My Wardrobe, Myself

The intersection of clothing, emotions, and life

My recent posts about my shoes (HERE and HERE) got me thinking about something very important when it comes to my closet (and possibly some of your closets as well). To a certain extent, it really doesn’t matter how many clothes, shoes, or whatever types of items we own. What matters are the things we’re actually wearing. The rest is simply “filler” that gives us a false sense of security that we have a sizeable wardrobe or “enough” to wear. In today’s post, I expand upon this concept, using the example of my shoes (since that’s fresh in all of our minds) to illustrate my points.

false sense of security

Do you THINK you have more viable options in your closet than you actually do?

The Number Isn’t the Real Issue

As I mentioned in my May 12th post, I currently own 28 pairs of shoes. This often feels like too many shoes given my present lifestyle, but if I were wearing all of them at least semi-regularly, I wouldn’t worry that much about the number. I’d likely put the brakes on new shoe purchases to cap the number that I own, but then I’d just wear what I have and let the overall number gradually decrease by means of attrition. As shoes wear out, or when I stop liking particular styles, I’d purge them and get my collection down to a more appropriate level for my needs and preferences.

But my primary issue isn’t that I have too many pairs of shoes in my closet. The real problem is that I have a number of shoes that I rarely or never wear. When I stare into my closet, I see what looks like a lot of footwear options, but can I really call them that if they’re never being chosen? If some of my shoes are only worn once in a great while simply because I feel guilty for having bought them, do those shoes even belong in my wardrobe?

When I wrote in my initial footwear “Rule of Ten” post that I wasn’t ready to own just ten pairs of shoes overall, that was only partially true. It’s not so much that I feel a strong need to have a semi-large footwear collection (opinions vary regarding what that means); it’s more about the fact that I have so many shoes already. If I take a good, hard look at what I’m actually wearing in terms of my shoes, I realize that I mostly reach for the same few pairs over and over again each season.

If I Were Starting from Scratch Today…

Most of my remaining shoes are fillers that I’m either not wearing at all or that I only wear occasionally just because they’re there. I probably wouldn’t purchase at least a third of my shoes today if I had it to do over again. There are various reasons for that strong assertion, but the bottom line is that I would leave those shoes in the store rather than take them home with me (or I’d return them if they were purchased online).

If I were starting from scratch today and visited a hypothetical shoe store that only carried the twenty-eight styles of shoes that I currently own, I’d have a relatively easy time selecting which ones to buy for year-round wear. I think I’d discover that I’d do fine with far fewer pairs, as I have a good idea which styles best suit my personal style aesthetic, the occasions in my life, and my comfort needs.

Of course, I’d have to try things on in order to make the right determinations related to fit and comfort, and it would also be helpful to view photos of my clothes to properly assess which footwear options would best fit into my wardrobe. But if I didn’t already own the shoes in question, I think it would be quite easy to choose the best options from among them. As the old saying goes, hindsight is 20/20. It makes sense that I would know now which of my shoes I should or shouldn’t have purchased, as I’ve had them all for a while and I understand the issues with some of them. Should I have been able to foresee those issues at the time of purchase? Well, that’s a different question, and one that I’ll examine later on in this essay.

The Same Would Be True for My Clothes and Accessories

I presented the example of my shoes above, but I believe the same would be true for my clothes, jewelry pieces, and other accessories as well.  There are simply a lot of items that I wouldn’t purchase again today if I were offered a “do-over.” I don’t feel all that bad about some of these pieces because they were either inexpensive or served their purpose for me over time. If I’ve worn something a number of times but no longer like it or it no longer fits me, the guilt factor is relatively low. But if I purchased an item and rarely or never wore it, I feel a tremendous sense of remorse. I feel like I should know better by now what will and won’t work. After all, I’ve been writing about my wardrobe for years at this point, and I’ve even written two books about shopping and wardrobe management. Clearly, I don’t always follow my own best advice.

The guilt causes me to delude myself about the truth of many closet items. In my heart of hearts, I know the answers. I know what should stay and what should go, for the most part. Sure, there are a few questionable pieces that I either need to take for a “test drive” or spend time trying to style before gaining clarity on their appropriate fate, but those are more the exception than the rule.  In most instances, I know why I’m not wearing a lot of my pieces – and I know that I shouldn’t have purchased them in the first place.

We all have our favorites, and most of us wear some garments, shoes, and accessories more than others. It’s the rare person who wears everything equally. If that’s you, more power to you, but I’ll probably always have an uneven distribution of wears among my closet pieces. I’m fine with that, but what I’m not fine with is having the false sense of security that comes from a large wardrobe with lots of filler in it.

We Can’t Always Know What Will Work for Us

We can’t always know what will and won’t work for us when we’re in the store or perusing an e-commerce site, and we sometimes we’re still not sure once we get things home. There are some intangibles like how we’ll feel in a given item, how comfortable it is, and how well it washes and wears. I’ve purged many a piece over the years because of discomfort, fussiness, and poor quality.

I’ve gotten better at figuring out in advance what might be fussy, uncomfortable, and problematic with garments, shoes, and the like, but sometimes I’m still surprised when what I thought was a gem ends up being a dud. Yet the hard part is letting go of a dud that cost a lot of money and cannot be returned.

Selling some of these items online has helped to assuage my guilt, but I only ever recoup a portion of my initial investment. That’s the nature of the resale game; just like a new car rapidly decreases in value once you drive it off the lot, wardrobe items can usually only be sold for a fraction of their original cost, even when they’re “new with tags.” Despite being able to earn some money for closet cast-offs, the time investment in the process can make the whole thing feel like a “wash.” I often can’t decide if it’s worth it or if I’d be better off just donating pieces like I used to and simply cutting my losses, but that’s a topic for another day…

Many of us think we like certain items – and maybe we do in theory, but that’s not what matters. For instance, I like the look of some shoes that kill my feet, and I love to gaze at footwear that I can’t walk more than a few paces in. I also admire many items of clothing that wouldn’t work on my body shape or have no place in my lifestyle. The hope is always that I’ll recognize such issues in the store or within the return window, but that won’t always be the case.

Sometimes these types of items taunt us every time we see them in our closets. We think of the money that was virtually flushed down the toilet, but you know what? We’re not going to be able to get that money back, and holding on to things just because we “messed up” won’t help us in any way. It will only make us feel worse about ourselves, especially if we’re not wearing the items in question – and aren’t ever likely to do so.

Enter “The Rule of Ten”…

So, what now? I no longer want to be under the false illusion that I have significantly more outfit options than I actually do. I want my closet to house only my working wardrobe and not a lot of filler and fluff. That’s why I decided to implement the Rule of Ten. I’ve only applied it to my shoes thus far, but I’ve already learned so much. I’ll be doing another shoe post soon to address my summer shoes that are “on the bubble,” and I’ll also give an update on decisions I’ve made about the “not summer” shoes I was unsure about.

There’s nothing magical about the Rule of Ten. It’s simply a construct that I put in place to help me gain increased clarity about which items are favorites (a.k.a. “all-stars”) and which are “benchwarmers.” I don’t believe that ten is the right number of items for me (or anyone else, for that matter) to own in all wardrobe categories, but it’s a place to start that feels comfortable to me. I may decrease the number in certain instances where I need fewer pieces, or I may split up certain collections like I did with my shoes (into summer and “not summer” groupings).

The number and the way I specify the categories matters a lot less than the end result and what I learn along the way. I want to get the “dead weight” out of my closet. I’m thinking what I’ll do soon is determine my Rule of Ten (or fewer) selections for my various wardrobe categories. I’ll then either place the remaining items in “purgatory(a.k.a. my holding zone) for a while or prioritize “trial runs” to see how I feel when I wear them.

I did that with a pair of shoes last week, and a short errand run was all it took for me to figure out where those shoes belonged (hint: it wasn’t in my closet!). The shoes ticked all boxes for me except the most important one – comfort, so it was time for them to go! Sometimes more than one trial run might be needed if the issue is more about styling, but if an item is uncomfortable or fussy, the decision can be made fairly quickly, as long as we’re honest with ourselves.


I’ve been gradually reviewing the various areas of my wardrobe. Just yesterday, I tried on all of my dresses and skirts, as well as the tops and toppers I typically wear with them. I’ll share my findings and thoughts from that experience shortly, but I’ll just say this for now… If your body, lifestyle, and/or style aesthetic have changed recently, it’s a good idea to conduct a wardrobe review. In some cases, all it takes is to look at everything and see how you feel about it, but I’ve found that trying things on can lead to some surprising results.

Some dresses that I thought were favorites had me feeling “ho-hum” – or worse. Due to the pandemic, I didn’t wear most of them in 2020, so it’s been close to two years since I put them on my body. A lot can change in that time frame, so I’m glad I made the effort to try everything on. Doing so eliminated the false sense of security I had about how many dresses I have to wear.  I feel much better now knowing the truth about that section of my wardrobe, and I plan to gain that same level of knowledge about all of my other closet categories soon. Stay tuned for more wardrobe evaluation posts, and feel free to share your thoughts about this one.

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43 thoughts on “Do You Have a False Sense of Security About Your Wardrobe?

  1. Sally says:

    Hi Debbie,

    It looks like you are getting a much better grip on your wardrobe and what needs to stay and go, following your analysis and trying on sessions.

    My thoughts on reading these comments:

    “If I were starting from scratch today and visited a hypothetical shoe store that only carried the twenty-eight styles of shoes that I currently own, I’d have a relatively easy time selecting which ones to buy for year-round wear. I have a good idea which styles best suit my personal style aesthetic, the occasions in my life, and my comfort needs

    “I believe the same would be true for my clothes, jewelry pieces, and other accessories as well.  There are simply a lot of items that I wouldn’t purchase again today if I were offered a “do-over.”

    I wondered whether this slightly different approach may work better or easier for you, rather than focusing on your Rule of Ten (or fewer):

    Start with your shoes, as you have done most of the analysis on them:

    1. Remove ALL your shoes from your wardrobe (summer and not summer)
    2. Only put back in your wardrobe those shoes that you would purchase again today
    3. Then retry them on to check that they suit your personal style aesthetic, the occasions in your life, and your comfort needs and if they don’t then remove these from your wardrobe too
    4. Put the rest of your shoes in your holding zone, out of sight, as they are not really part of your wardrobe and as you say, give you a false sense of security
    5. If you find that you have an occasion where you do not have the right shoes in your wardrobe, recheck to see if any in your holding zone meet that need
    6. If they don’t then you know to get rid of those shoes from the holding zone
    7. Then add the type of shoe that you were missing onto your shopping list
    8. If you find the shoe on your shopping list, try it on at home to make sure it meets ALL your criteria. If it’s not comfortable at home, it won’t be comfortable if you were to wear it out
    9. Return any that don’t meet all your criteria within the return window

    Then repeat this next for ALL your clothes at once, as you have already started to do this, then jewellery and accessories.

    When you do this for clothes, step 1 should be relatively easy as you have a good sense of your style now, but step 2 you will probably find that you remove quite a few more pieces due to fit issues, as you have already started to find out.

    It doesn’t matter how many items you end up left with, even if they are more than 10, all that matters is that everything in your wardrobe you will wear today, it suits your current style, size and comfort. The right numbers for your wardrobe will naturally evolve from this process and this will be different for everybody.

    You can then easily get rid of pieces in your holding zone if you don’t end up reaching for them and you also have a very specific shopping list for things you actually do need for your current lifestyle, and not “nice to haves”.

    You will have enough items left so that when you are looking for items on your shopping list you aren’t desperate enough to have to settle for something that isn’t quite right.

    You have already learnt from past experience that if you buy something that’s not quite right, you keep on buying more items until you eventually find the right one.

    Then you end up splitting your wears, as you only reach for the perfect one, so you have ended up wasting money on the clothes that you settled for.

    I hope that this may have given you something to think about.

    Regards Sally

    1. Sue says:

      I think we all have different reasons for the size of our wardrobe. I crave options. I arrived in Europe decades ago with a backpack full of mostly casual summer clothes. In my first years in Europe, I can remember being desperate for a winter coat, buying suede heels on the way to a wedding, and urgently searching for a party dress on the day of a party. Years later, when I had put on too much weight one time, I can remember running into a department store with my family already dressed and waiting in the car to find a dress, suit, anything for a wedding that afternoon. And years after that, I recall another frantic shopping day with my grown up daughter, looking for something, anything I could wear to an outdoor wedding dinner after a heatwave hit. (That’s one of the few ‘desperate’ purchases that I really love and still own.) Nowadays, I own clothes (and many shoes and accessories) that I seldom wear, but I love them all and I am ready for anything: whether it’s a casual barbecue dance at the beach or an elegant wedding in the snow, I have plenty of options. And that makes me happy indeed! I regularly purge items that become worn, out of date or uncomfortable but if I can imagine that I might have any use for something (like slightly frumpy but excessively comfortable shoes for sore feet at a wedding), I will hang onto it gladly. I much prefer a well-stocked wardrobe to a mad, last-minute dash to the shops.

      1. Debbie Roes says:

        Thanks for your openness in sharing your experience, Sue. I appreciate when commenters are willing to be open about their own struggles. I agree with you that having a well-stocked wardrobe is preferable to the “mad dash” to the shops. I remember one time close to 20 years ago when I needed a dress for a holiday party and I waited too long to search for it. It was SO stressful and I wasn’t very happy with what I ended up with. I can definitely relate to what you wrote! It’s good to be ready for anything, even those occasions that don’t occur all that often.

    2. Debbie Roes says:

      Thanks for sharing these suggestions, Sally. You’ve given me – and I’m sure others – some food for thought. I remember a blogger who did something very similar to what you suggested. Although I don’t remember all of the specifics, I recall that she called her “holding zone” the “boutique,” and she would periodically shop her boutique when she found a need to add to her wardrobe (when seasons changed, etc.). I liked the fact that she shopped her closet (the “boutique”) before shopping in stores. I think a lot of us focus too much “out there” and not enough on what we already have. The Rule of 10 has been helpful for me with me shoes. It’s not so much about the number; it’s more about the fact that it pushed me to focus on what I have and evaluate it more fully. No matter how we go about it, I believe that such evaluation is beneficial.

      1. Sally says:

        Hi Debbie

        I had to go through my whole wardrobe using the steps I outlined above because I have retired, so no longer had any use for my smart work clothes and work shoes. I gave them to charity as in good condition, so they may be of use to other working women.

        I also gave away some shoes that were too high or were uncomfortable and hurt my feet, so there are no shoes in my holding zone, which is a wardrobe in the spare bedroom, out of sight.

        I gave away any clothes that weren’t my style anymore or I didn’t like or weren’t comfortable.

        The only clothes in my holding zone are those that are still my style, I like them and they are comfortable, but unfortunately are now too small as I have put on weight.

        Imogen Lamport said that there’s no need to be a slave to trends, unless you want to, just pick those you like and suit you. But if you don’t want to look old fashioned by wearing outdated style of clothes, see if you can find items in a similar style to yours in the shops today.

        Most of my clothes and shoes have been bought in the last 2 years since I retired, to suit my new lifestyle and weight, so similar items can be seen in the shops today and I also have a classic style, so they don’t date too quickly.

        Therefore everything in my wardrobe, both clothes and shoes, I would still buy today, I wear them all, they suit my style, body shape, are comfortable and suit my lifestyle.

        As my wardrobe is no longer cluttered, all my clothes now hang on matching wooden hangers, which I treated myself to, arranged by type, length, colour and they are evenly spaced so that they look neat and I can easily see what I’ve got.

        All my shoes are kept in their original boxes and my handbags in their original cloth bags, to keep them all in good condition and dust free.

        My wardrobe now looks like an upscale boutique and is a pleasure to open and peruse.

        If I do lose some weight, I will try on the clothes in my holding zone and if they fit they will make it into my main wardrobe and the clothes in my main wardrobe that are now too big will go into my holding zone, as undoubtedly the weight will go back on!

        Sometimes, however careful we try to be, we all still make mistakes. I bought a top the other day which seemed great when I tried it on at home, but when I wore it out for the day the neckline irritated me. I wore it out one more time just to make sure, then gave it to charity. There was no point putting it in my holding zone, even though I had only worn it twice, because if I wore it again it would still irritate me.

        Obviously, as seen by the comments, everyone has different methods of sorting out their wardrobe, how many clothes they are happy to have and how old their clothes are. There is no right or wrong, I am just sharing what I have done, in case anyone else finds it helpful.


  2. Gail says:

    There are way, way worse things than feeling you have too much clothes or anything for that matter. You are hurting no one! My parents’ andin-laws’ generation felt secure in stocking up on household items such as toilet paper and soap. Security is important! I recall an article you wrote–or two–about set-point. That is to me also about security. If you can feel comfortable with owning and perhaps hardly using certain items in your life, go for it. Security is hard to come by. A full pantry and refrigerator sometimes make me feel happy–perhaps secure. We have a stash of hurricane supplies that we feel more secure possessing. It’s okay. It’s only when the excess bothers you that it might be consiered to cut some of it. I feel better with fewer clothes, but please do not think I am criticizing others for feeling better–more secure–with lots. I know you think I am judging those with big wardrobes, but I am not. I AM trying understand, though.

    1. Debbie Roes says:

      I think we all have our items that we stock up on, Gail, and probably more so after what we’ve all collectively gone through! I know that we have more toilet paper and non-perishable food on hand than we used to. Many of our ancestors went through very difficult times like the recent/current pandemic, and now we understand their tendency to hang on to things for security’s sake. Yes, people definitely hold on to wardrobe items to feel more secure, but what I’ve realized is that such security can be false, at least in my case. If I’m not going to wear those surplus items, then why have them around? Of course, there are some gray areas, but that’s what I’m working to address, in addition to letting go of the “dead weight.”

  3. Juhli says:

    It sounds like you are gaining insights into why you hold on to items you don’t wear. I was introduced to the concept of sunk costs many years ago. Letting the money we spent in the past cause us to keep something that no longer works for us or makes us unhappy/uncomfortable doesn’t change at all the fact that the money was spent and is gone. It sounds like you are near to reaching the point of taking what you can learn from those sunk costs into your future spending decisions and letting go of the items that make you feel guilt or a false sense of security. Well done!

    1. Debbie Roes says:

      The sunk cost theory is so valuable, Juhli, and it explains why many of us tend to hang on to possessions that aren’t serving us – or even to people and relationships in whom we’ve invested a lot of time and energy. I remember when I was helping a friend clean out her closet years ago. She was reluctant to let almost anything go, even if she hadn’t worn it in years. She would tell me the designer or say something like, “that’s cashmere.” This was before selling things online was as popular as it is today, which might have helped her to let go of more of her old clothes. I’m usually pretty good at letting go of clothes, but I’ve had a tougher time with shoes for some reason. But as I peel away more layers, I’m getting pickier about what I should keep, which I think is a good thing, regardless of how much something originally cost.

  4. Murphy says:

    Great insights on this topic! I think that separating “what I would buy right now” is a good exercise. Then I can shop what’s left if I feel the need. One problem I have is that I get sentimental about certain items and feel guilty getting rid of them. For example, I have a lovely, expensive blouse that I bought with my husband’s help when we were on vacation in Scotland 5 years ago. It’s pretty, but I only wear it once or twice a year and probably wouldn’t buy it now because it’s a little showier than what I usually choose. But it was such a great trip and my husband was so generous and he thinks it’s pretty and… You can see the problem. There are quite a few things like this in my wardrobe and It looks like I have a lot to wear but I often find myself scrambling to come up with a presentable outfit because 3 or 4 things are in the wash and NOW what? Thinking that I shouldn’t have more than some magic number including the bench-sitters isn’t helping. Probably I should at least move the sentimental-only items to their own section as part of facing reality.

    1. Debbie Roes says:

      That question (“Would I buy right now?”) can be SO helpful, Murphy. I like “Does it spark joy?” as well. It’s tougher when it comes to sentimental items, like your blouse from Scotland. Some people choose to keep such pieces in a kind of “keepsake box” to look through occasionally, while others prefer to take some photos (perhaps with them wearing it) and then pass the item on, if they no longer enjoy wearing it (or maybe never did). It’s an individual choice, but I don’t think our loved ones want us to hang on to gifts from them out of guilt. I agree that maybe isolating your sentimental pieces and moving them to a separate area is a good first step to take. Then you’ll have a better sense of what you really have in your “working wardrobe.”

  5. I think zeroing in on the FALSE sense of security is a key insight here. I get a sense of security (among other things) from having a large wardrobe, but I wear everything I have, and am set for a lot of different situations, so that security is real. What would happen if you followed the initials steps Sally laid out above? How does it feel to look into the closet and see only things that you would buy now? Is it enough? Are there common lifestyle events/situations you aren’t prepared for? Do you not have enough to make your laundry cycle work? Or is it just a feeling of not enough? If it feels like not enough, I’m wondering whether this feeling, combined with how difficult you seem to be to fit, would cause you to want to quickly fill the closet up again with not-really-right pieces that start the whole full closet false security cycle again.

    1. Debbie Roes says:

      Those are some good though-provoking questions, Sally. I’ve done quite a few wardrobe challenges in the past and I’ve had mixed results. Part of my issue is that I’m “moody” with my clothes (and in general), so my answers to “Would I buy it now?” might vary from day to day. That’s a big reason why I have a holding zone, as sometimes I will “rescue” items that I thought I wanted to pass on. It’s great that you wear everything you have, even though you have a large wardrobe. That’s why I always say that there is no one right number for everyone. I always have to consider the “closet set point” that I wrote about years ago (, as if I pare down too quickly, I get the feeling of scarcity that can lead to “panic shopping.” It can be a delicate balance…

  6. Vildy says:

    As usual, you explore a very complex and vital topic. For some reason, I don’t feel secure about my wardrobe even though it tends to be sizeable and I have frequent reactions of delight at outfits I’ve put together. Probably the only things that help me feel secure are whatever money I have in my checking account (no savings nor investments) and some open lines of credit ( cards are zero’ed out), as well as a working heater, air conditioners. I guess I’m a real basic gal, that you would never figure out from my wardrobe/outfits. 😀

    So I start to think Security against *what? In the above cases, I feel better thinking I might be able to meet emergencies and, in the case of climate
    control, I won’t have to suffer. And when the furnace broke this winter boy did I suffer until they were finally able to figure out what was wrong. It wasn’t horribly cold in the house but I figured out that some days I had as many as eight layers! And the huge bill (my inexpensively priced GoTo
    furnace guy had retired) had to go on a credit card. Though the company had its own payment plan – hmm, why would they have developed that?

    But clothes. What are the security issues behind that? I need shoes to protect my feet and allow me mobility and, in treacherous weather, keep me upright. I need things like winter coats, gloves, hats and (all of mine are always ineffective no matter what design I try) umbrellas. Otherwise, I
    think the key is to examine what our social/psychological needs are. Why do people (women?) go so crazy about having the “right” outfit for
    an event? What are we trying to prove to others (sometimes ourselves as well?) by our appearance? It seems to me this is not a wardrobe
    issue but an anxiety issue. What pejoratives are we trying to avoid? As a corollary, I recently stopped reading a fashion forum that is known
    for being polite and positive but, in fact, it became clear to me that a proportion of people were concerned about not being misidentified as
    a type of person they scorned. So, it wasn’t *for* themselves, except in the sense that it was *against* others. It put me in mind of that Fug
    Girls site except that they were more self-aware and accepting of their disdain for certain others and must have been quite successful in
    monetizing that by attracting readers who wanted to deride but also keep on the right side of judgment.

    I think a good place to start finding out the why behind the drive for security is to use a downward arrow technique.
    You start with one proposition like: If I don’t find or have the right outfit for attending a wedding, then….
    You complete that sentence with the worst consequence you fear. It often comes down to What kind of person I would be.
    Maybe it’s someone who has exposed herself to ridicule or reveals she doesn’t care about the happiness of others…
    And that brings its own consequences in your mind. And you continue down the page until what you really fear – what threatens
    your security – reveals itself to you.

    So it looks like I have set myself a task, eh. 😀

    1. Sally says:

      Hi Vildy

      Thanks for sharing, you raised some interesting questions as to why clothes provide security, which will be different for everybody.

      I grew up with low self esteem and had trouble making friends, I didn’t really fit in and I felt anxious and tried to avoid social gatherings. I was also teased for being tall and had trouble buying clothes that fit me, so I was very self conscious.

      When I got a job, I found working in the city was very competitive. I lived by the saying “dress for the job you want, not for the job you have”. I saw managers and executives in smart, expensive clothes and accessories, which put mine to shame and I felt inferior and not good enough. In order to give me the confidence to apply for promotions or new jobs, I wanted to look the part, so I started to buy expensive clothes and bags too.

      I needed other people’s approval. I believed that I must fulfil certain criteria expected by society – beauty, thinness, success, qualifications, wealth, status and popularity. My self-esteem was tied up in external and material things.

      I used to buy “just in case” clothes, which gave me the security that if I was invited to an event, like a wedding, a day at the races, a black tie function, then I would have the perfect outfit all ready, so that I would look great and fit in and it would give me confidence.

      As I moved up the corporate ladder I was invited to more exclusive and sophisticated events. I would wear my designer clothes and bags as armour to hide my insecurities, so that I looked like I belonged there.

      However, at these events there were always people who were more successful and richer than I was, who made me feel less than them, because however great the things were that I had, they had something better. Trying to keep up with them was an impossible task, I was never satisfied with what I had, I was always trying to find something better to be like them, which I couldn’t afford to do.

      A lot of the “just in case” clothes I bought ended up not being worn, either because the imagined event didn’t happen, or by the time it finally did the clothes weren’t my style anymore or didn’t fit or weren’t appropriate for the actual dress code. I had a huge inspirational wardrobe of clothes and shoes I never wore. I wasted a lot of money.

      Now I no longer work and I suffer from depression and anxiety I rarely leave the house and I don’t go to any events, so I no longer need to dress to impress or to fit in.

      I have also put on so much weight that the pleasure of buying and styling clothes has diminished as nothing fits or looks good on me anymore.

      I no longer buy fashion magazines or follow fashion blogs as they create FOMO and make you think that you need to have the latest designer items to show how successful you are. They just make me feel worse about myself and my body.

      I now wear clothes just for me, for my current lifestyle and body size, that I am comfortable at home in or for the odd trip to the doctors or shops, the occasional meal out and for walking the dog in. I don’t need as many clothes as I used to, I don’t buy “just in case” clothes anymore and I wear all the clothes that I have.

      It’s just me, my husband and my dog and they love me and accept me whatever I look like or am wearing, so I now get my security from their love, not my clothes, or what other people think of me.

      1. Vildy says:

        “It’s just me, my husband and my dog and they love me and accept me whatever I look like or am wearing, so I now get my security from their love, not my clothes, or what other people think of me.”

        I would wish that for every person and creature in the world.

      2. Debbie Roes says:

        I appreciate your openly sharing about your life and some of the issues you’ve had related to clothes over the years, Sally. I’m sure a lot of people can relate to what you wrote. I know I could… I think a lot of my buying has a lot more to do with how I want to feel and “safeguarding” myself from bad feelings than it has to do with real wardrobe needs. Because how many clothes do most of us really need, especially if we have simpler lifestyles like you and I have. It’s so wonderful that you’re now dressing just for yourself, and that you feel accepted and loved for who you are. I second Vildy’s wish that everyone would feel that way!

    2. Debbie Roes says:

      Vildy, thanks for your detailed and introspective comment. You’re right that our issues around “security” with our clothes usually have more to do with social and psychological issues than actual concrete lifestyle needs. I know that anxiety plays a very large role in the whole thing for me, which I’ve written about on numerous occasions. I like your “downward arrow,” “if then, what?” technique. I think we can learn a lot by asking those types of questions! I agree that it’s often about what type of person we would be – or at least what type of person we would be PERCEIVED as. Hmm… lots of food for thought in your comment!

  7. Gail says:

    Once someone said in a conversation among three of us that “He only THNINKS he is happy.” Another said, “But if you think you are happy, aren’t you then happy?” I wonder is when you feel secure you are secure?😃

    1. Debbie Roes says:

      Very astute comment, Gail! I definitely think the way we feel is of paramount importance. To a large extent, happiness and security are “inside jobs” (beyond the point where one’s basic needs are taken care of, which is true for most of us).

  8. Katrina B says:

    Absolutely, I have a false sense of security about it. I’m sitting here thinking I have the exact right number of tops and bottoms to create the exact right outfits for work, travel, and lunch with the girls. At the same time I know I haven’t worn 99% of those clothes for 16 months and I have no idea how they fit or look anymore. I think trying everything on and a session of “would I buy it now” are much needed at this point.

    Thank you for sharing your discoveries with us – I always come away with something interesting to think about and apply to my own life.

    1. Katrina B says:

      I decided to take a stab at the try-ons this weekend, and let me tell you it is EXHAUSTING. Well, you probably know that since you’re already in the midst of it. It took me more than 4 hours to do 4 pairs of pants (matching tops and shoes to them) but I think it was worth it. I have documented 23 outfits that I like and are comfortable. Only one shirt had to be set aside – I love it, but it doesn’t really “work.” Over the next few weekends I will continue the try-ons – it’s pretty fun, in spite of being time consuming and tiring.

      1. Katrina B, kudos for taking on the task! For people who have not been wearing their usual clothes during the pandemic, this is an especially good time to revisit their wardrobe.

    2. Debbie Roes says:

      That’s so great that you did some try-ons this past weekend, Katrina! I agree that it’s an exhausting process, which is why it can be good to do it a bit at a time (that’s what I’ve been doing, too). It IS so worthwhile, though, as we often don’t know the possibilities in our closets until we do some experimentation, especially after “weird times” like what we’ve all recently endured. Congrats on documenting 23 outfits that you like! That will take you a long way! And great that you only came across one top that didn’t work. I hope you continue to experience such great success with this process.

  9. wjgravity says:

    I like your idea of what would you buy if you had to start over. I have some categories I know I would keep nearly everything (T-shirts that I wear to work. Most are souvenirs from traveling for work and personal trips, and I rotate through the collection pretty often), others I’d keep a lot less for style/comfort reasons (see my dresses that rarely get worn), and others I would keep purely because I can’t find replacements that actually fit.

    I’ve stopped shopping/decluttering my closet lately since I spent most of 2020 very sick and lost an unhealthy amount of weight. We are working to fix that, so I’m looking forward to once my weight settles back to its healthy state to trying some of the methods you and the other commenters to rebuild a wardrobe that works for me (and my life) and not that has been acquired just because I *needed* something specific for an event, or because something *mostly* fit.

    1. Debbie Roes says:

      I’m glad to read that your health is improved, mjgravity, and that you’re gradually getting back to a healthy weight. It’s smart to put the brakes on shopping when one is going through a transition or a time of uncertainty. I wish you the best of luck with trying some of the methods laid out here for gaining clarity about your wardrobe and cultivating a workable wardrobe that you love. It’s good that you believe you have some wardrobe categories that are in good order now. I hear you on keeping some items because it’s hard to find replacements that fit well (I’m looking at you, pants…).

  10. Cathie Perkins says:

    For clothes or shoes that I love the look of but would be impractical for my lifestyle I save them on Pinterest. I have a board called dresses for a dreamlife 😉 and that’s where they go. I can admire them any time I like but I don’t own them. I have in the past purchased ridiculous high heels and referred to them as wardrobe jewellery as they just looked pretty on the shelf but impossible to wear. Now they are saved on Pinterest too.

    1. Debbie Roes says:

      I love the idea of Pinterest “dream boards,” Cathie. We definitely don’t need to own all of the clothing pieces that we admire, especially when they serve no real purpose in our lives. I like the term “wardrobe jewellery,” too. I think I may start a Pinterest dream board myself now, as I certainly don’t need fancy dresses or super high heels!

  11. Jenn says:

    So many of the clothes I have in my closet could be described as filler, and they were probably were purchased to give me a false sense of security that what I have is enough.

    The thought of going through those pieces, item by item, and determining which of them I’d buy again has seemed overwhelming, but it’s something that I’m sure I should do. I’m sure that even some of my newer pieces are items I would not repurchase.

    For instance, I have three T-shirts that I most often reach for, summer after summer. And my scarcity mindset tells me they won’t last forever, and I need to find more. Though there may be some truth to that, when I couldn’t find anything I like as well as those three, I settled for a few I don’t enjoy wearing nearly as much, resulting in a waste of time and money. With the addition of these shirts, my wardrobe (and my self-esteem) is left in worse shape than before.

    I think I’m ready to (slooowly and by season) try the method Sally described. I’ll make sure I leave myself enough to wear, but no more. I am hopeful that I’ll gain clarity from this experiment, and probably more.

    1. Debbie Roes says:

      I agree that going through all of our pieces item by item seems overwhelming, Jenn. While I admire Sally’s “all at once” type of approach, it feels daunting to me, which is why I’m doing things a bit at a time, much like Katrina described above. A slower approach is also good for those of us who might be prone to panicking and going out shopping due to a feeling of scarcity. The fear element is why I often set my castoffs aside for a while before they actually leave my home. I do “rescue” things from time to time. I think it’s great that you have three favorite summer t-shirts that you reach for over and over again. I always wish I could know in advance which pieces would fit that type of description so I could purchase a few more. But when I make such a determination, the items usually aren’t available anymore – sigh… Good luck with going through everything, and I hope you gain a lot of knowledge and clarity from doing so. It’s helping me a lot to do it, and I hope that my sharing my process is benefitting others.

  12. Maggie says:

    Hi Debbie,
    As always, your posts make me think…I wonder if anyone has read the book, “Scarcity: Why Having Too Little Means So Much” I can see understand the points that everyone has made about security.

    I am going on close to 50 days with my stuff still in storage. I have bought a few things at goodwill. In one case, I found a pair of jeans that fit me well and bought the same style in a different wash on Ebay.

    I have bought a set of gauze joggers and a black-white space dye maxidress (my first).

    I suppose the thing I like about this experiment is I don’t try to find the “perfect” thing.
    I am just seeing if I can lower my expectations and buy something that is “good enough” for now.
    For example – it just got hot and I made sure that I had a pair of shorts and 2 tanks tops from Goodwill to wear since my summer stuff is all in storage.

    The funny thing is that in stores, sometimes the XS and S is all sold out while in Goodwill – at least in tops – there are plenty of size XS and S. I like that they put the print tank tops in size small on one rack so it is easy to browse.
    (It is rather strange not to have shopclerks watching you.) The other strange thing is that I try on things that I wouldn’t normally try on just to experiment. So, now I am going once a week to Goodwill, the nicest one in my area, as a “retail experience” and to see what they have. It is very low-stress shopping.


    1. Maggie says:

      FYI – I am thinking of volunteering at the Goodwill where I shop just to get myself out of the house and play with clothes without spending!

    2. Debbie Roes says:

      That sounds like an interesting book, Maggie! That’s great that you’re navigating your move process well and have found some great clothes at Goodwill. Volunteering at that Goodwill sounds like it could be a win, win situation for you – great idea! I also like what you said about not having expectations of “perfection” from new purchases. Sometimes “good enough” really IS sufficient. Buying resale items can be a great way to experiment with new styles and silhouettes. I wish I wasn’t so sensitive to fragrances, which makes it difficult for me to buy used items anymore, but I’m glad that it works so well for you and others.

      1. Vildy says:

        About “good enough really IS sufficient”: I often get ideas in my head of how I want/anticipate items to be. Of course this applies to online shopping –
        where things can really turn out different but also it happens to me with in-person shopping! I sometimes see with my mind’s eye only! My husband
        had great advice for this kind of disappointment. He puckishly suggested, Celebrate the differences. And you know, it works to blast apart idealistic

        1. Debbie Roes says:

          Your husband sounds like a wise man, Vildy. I’m going to keep that in mind, as perfectionism is often a recipe for unhappiness!

  13. NATALIE K says:

    I must say that Sally’s suggestion for going through your closet makes perfect sense to me, but I would definitely have to take it slowly because of my health and the number of clothing items I own. I won’t be able to do it by myself, but my girl friend has said she will help me. We did that two years ago and she just can’t believe how much I’ve purchased since then. She doesn’t buy clothing or accessories, BUT she buys expensive creams and household items. We all choose to spend our money on different things!! I have learned so much here today!!

    1. Debbie Roes says:

      I’m glad Sally answered you below and made some good suggestions, Natalie. I hope her method will be helpful for you. You don’t have to do it all in one day if it feels overwhelming to you, and if you put things aside in a sort of “holding zone,” the decisions you make don’t have to be final. I find that makes things less scary and overwhelming for me, as I can always “rescue” an item later should I choose to do so (which DOES happen, especially since I tend to be very emotional about my clothing and may either love or hate something based upon my mood in the moment).

      I know it’s hard when our friends or family members judge us for how many clothes we buy and have, but most people have their “things,” as your friend does with the creams and household items. From what you’ve written in the past, it sounds like you love clothes and fashion and like to express your creativity through what you wear. I’m like that, too, so I get it. When we don’t wear some of the things we buy, it can feel bad, but we can’t always know what will work (as I wrote). We can only do our best to learn from any mistakes that we might make.

      Good luck to you with going through your wardrobe. I hope you’ll benefit from the experience with both a more streamlined closet and some newfound knowledge about what does and doesn’t work for you.

  14. NATALIE K says:

    I am afraid of feeling I don’t have enough that it will send me on a shopping spree. This is what happened to me years ago when my girl friend helped me clean out my closet. But she said I had to get rid of things, so I did. Now I know better and would just put them in a plastic tote for later.

    1. Sally says:

      Hi Natalie K

      I definitely think you should take it slowly with your health issues, especially if you have a lot of clothes, so I suggest that you just do one section at a time, e.g. tops.

      The idea of the way that I suggested, is so that you have LESS clothes that you have to try on. You don’t have to try all your tops on.

      After taking all your tops out of your wardrobe, you only put back in your wardrobe those tops that you what you would still purchase today, as you still like the style and they suit your lifestyle today.

      Then you ONLY have to try on those tops you have put back in your wardrobe, to check that they still fit and are comfortable. If they aren’t then you remove those from your wardrobe again too.

      The reason I suggested to put them in a holding zone out of sight, rather than getting rid of them straight away, was to avoid the feeling that having less in your wardrobe may send you on a shopping spree or you may find that you have an occasion where you don’t have the right clothes in your wardrobe.

      The first thing you would do then, is to shop your holding zone, to see if there is something that you already have that would suit that need and then you can put it back in your wardrobe.

      You only need to go out and purchase something new if you don’t have anything in your holding zone that would work.

      It’s great that your friend is going to help you, but definitely put things in your holding zone rather than being influenced by her to throw clothes away that you might later regret.

      The only time to throw something straight away is if you definitely know however desperate you may be, you would never want to wear that item again, as it’s no longer your style, it’s not comfortable, it doesn’t fit right or it’s too worn out.

      Also, remember this exercise is all about YOU. Your friend may have a different style aesthetic, a different body shape or lifestyle and a different number of clothes in her wardrobe and this will influence the advice she gives, so you don’t want to end up with a wardrobe that she loves, but isn’t right for you.

      It’s ok to get a second opinion if you are on the fence about something, but you want to end up with a wardrobe of clothes that YOU love, that you want to wear, that suits your lifestyle, that is comfortable and fits right and that you have enough clothes in your wardrobe for the different occasions in your life.

      I hope this helps, take your time and have fun.


  15. NATALIE K says:

    Sally, Thank you!! That really does help!!

  16. NATALIE K says:

    I’m in more of a predicament then I’m sharing. My closet is full of Fall/Winter season clothing. I’m living out of totes right now with Spring/Summer clothing. Just about everything is new. I need to wear these items to even have an idea of what works for my Spring/Summer clothing. So now that we are back out that’s what I’m dong. Under my bed are full of totes with clothing. My coat closet is full of course of coats plus sweaters. Hope this helps to explain.

    1. Debbie Roes says:

      Just take things one step at a time, Natalie. I know that it can get overwhelming. I’ve been there myself many times. If you can pause or at least dial back bringing more items into your closet, that will help. That way, you can focus on evaluating what you have so you can see if you have any true wardrobe needs. I know that is easier said than done, but if you can stop online browsing, that will make not buying easier. I know that for myself, I will always find things to want if I look. Also, focus on evaluating the current season and worry about sweaters, coats, and the like later. Good luck!

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