My Wardrobe, Myself

The intersection of clothing, emotions, and life

In my last post, I began a two part series (or maybe more…) on depression and anxiety and what we can do to experience a greater level of happiness and peace in our lives. I’m grateful to all those who responded to that post, either directly on the blog or via email. I continue to ponder these issues and will offer my own tips and those of others in an upcoming post. However, since I’m not ready to go with that quite yet, I’m going to write about something else that I’ve been thinking about.

For almost two months now, I’ve been doing a modified version of the “30 for 30” remix challenge. My reason for doing this was to shift my focus from what’s “out there” in the stores and online to what is already in my closet. Since this is the time of year when there’s a “big sale” seemingly every other day, it’s difficult for us recovering shopaholics not to get caught up in a major case of FOMO. I also got a lot out of doing a similar challenge back in April/May (see my recap here), so I thought it would be helpful for me to do an encore.

essential wardrobe challenge

It can be helpful to challenge ourselves to dress with less for a period of time.

How the Challenge Works – and a New Rule

Here’s a reminder of how this challenge works, including a new rule I’ve instituted this time around:

  • I will be dressing with 30-item capsules for both my “out and about” and at-home wardrobes for the months of November and December.
  • Instead of selecting my capsule items at the beginning of the challenge, I’m building them organically as I go, adding new pieces until I reach 30 items in each capsule while also tracking how often each capsule item is worn.
  • Only clothing items are included in my capsules, but I’m also keeping track of my accessory pieces (shoes, jewelry, etc.) and how often I wear them.
  • I’m keeping an outfit journal for my “out and about” ensembles, rating each outfit and jotting down what did and didn’t work and why.
  • NEW FALL RULE: I can swap items out of the capsules for either weather or style-related reasons. For the latter, the swapped out items will go “on probation,” which means that they may be potentially eliminated from my wardrobe. At the end of the challenge, I will re-evaluate these items and see if using them in new combinations changes the way I feel about them, but I will pass on anything that is uncomfortable, fussy, or unflattering.

I’m really glad I decided to take on this challenge when I did because it has been enlightening. I will do a full debrief in January, but I want to share a few thoughts and insights with you today.

Timing is Everything

The fact that I opted to do the challenge around the time when the seasons changed ended up being particularly instructional. This varies a bit year by year, but the warm weather where I live typically lasts until sometime in November (this warm weather doesn’t begin until late June or July, so things even out…). This year we got lucky and it was still quite warm until right around December 1st, when the overcast days set in and the temperatures dropped. Until that time, my challenge was proceeding very well and I was happy with the pieces I had selected and the outfits I was wearing, but then things started to go awry.

This challenge has led me to realize that there is very little crossover between what I wear when it’s warm out and when it’s cooler. I don’t know if this is unique to me, but it’s almost like I have two disparate wardrobes for the warm and cool months. When I embarked upon the challenge, I thought that I could perhaps just swap out a handful of things to navigate the weather shift, but I’ve ended up swapping out quite a few items. That’s okay, though, as it’s made me do a lot of thinking. I’ve also made notes about all of my outfits that have helped me to see where things have been going right and where they’ve been going wrong. In my wrap-up post, I will outline any patterns I noticed in these notations, but there’s something that’s already quite clear to me.

It’s All About the Pants

In my post introducing this challenge, I mentioned that I had purchased a few pairs of looser-fitting pants for the warmer months, including printed options. These pants have been game changers for me in that they opened up lots of new outfit possibilities and increased my comfort level dramatically. I enjoyed wearing these pants so much that I was sad when it became too cool outside for me to wear them any longer.

Since the beginning of this month, I have mostly been wearing jeans and black pants. I haven’t been nearly as happy sporting these bottom pieces as the ones I wore during the summer months. Part of the reason for this is that jeans are less forgiving and aren’t generally as comfortable (for me) as other types of pants, including my new summer pants. But that’s not the biggest reason for my discontent. I’ve recently noticed that none of my jeans are quite long enough, thus I end up pulling them down to try to get some additional length. This decreases my comfort level, as the waistband of my pants digs into my high hip area, which doesn’t feel very good at all!

People always tell me that I’m lucky to be so tall, but there are definite drawbacks to being well above average height. Sadly, even “long” or “tall” pants are usually still too short for me, but because finding pants that fit my proportions are difficult enough already, I have often chosen to “settle” for the length being half an inch or an inch too short. I thought it would be no big deal or that I could stretch the pants out or wear lower heels, but it never quite works out all that well. The end result is that I’m unhappy with many of my outfits because they’re not quite right. Additionally, since I prefer to wear heels over flats, some of my shoes just don’t work with the pants I predominantly wear, so they end up gathering dust in my closet. Clearly, searching long and hard for pants and jeans with longer inseams needs to be my top shopping priority in 2019.

It May Not Be Pants for You…

I know that most of you don’t share my specific wardrobe challenge outlined above, but perhaps there’s an area in which you’re settling of which you’ve been mostly unaware. Maybe it’s a different fit challenge or it could be a color or fabrication issue. You may end up buying things that aren’t quite right simply because they’re on sale or a “good deal.” Doing a challenge like the “30 for 30,” Project 333, or similar can help to highlight problems that you weren’t aware of previously.

It’s amazing how crystal clear wardrobe problems can become when we push ourselves to dress with less. Travel can definitely highlight issues we have with our clothes. For instance, have you ever been on a trip and struggled to get dressed because you neglected to pack a particular item? Or maybe you packed too many similar pieces and not enough variety, or too many prints and not enough solids to ground them. It could be that we need to improve our packing prowess or it might be that our wardrobe at large needs work. Either way, traveling or doing challenges like mine can be very educational in terms of our wardrobe needs and the degree to which we are or aren’t meeting them.

I’ve identified other issues besides pants length that I will mention in my challenge recap in January. I was surprised that I didn’t notice these things previously, but when I was working with my entire wardrobe, they were simply easier to overlook because I had so many items to choose from when getting dressed. Not recognizing my “blind spots” has led me to focus on the wrong types of purchases when shopping. Sure, I often bought some great pieces, but they weren’t the ones that would add the biggest bang for their buck to my wardrobe. It’s wonderful to have a lot of pretty tops and toppers, but if the pants they’re paired with are substandard, the resulting outfits won’t be “10”s. If I want more higher ranked ensembles, I have to do the work to find better pants.

Next Steps

In addition to finishing out my challenge (I will stop at the end of the year or when I reach 30 “out and about” outfits – I’m up to 26 so far), I’m going to do a few other things to deepen my learning and help me dress and shop better moving forward:

1. Formulating Seasonal Capsules

I’m going to formulate seasonal capsules out of my existing wardrobe items. Maybe I won’t have many pieces that do “double-duty” for both warm and cool weather – and maybe that’s okay. However, I would like to identify what I view as my core items for both conditions so I better understand what I’m working with. If there are gaps between what I have and what would be ideal, I will make note of them. I will also list all of the items that serve the same basic role in my wardrobe (e.g. multiple black and white t-shirts that are interchangeable and potentially redundant).  Through doing the challenge, I saw that I have multiple items that are so similar that they don’t add a whole lot of value to my wardrobe. More on this in my recap…

2. Outfit Creation Sessions

I used to spend a few hours every month or two putting outfit possibilities together and photographing them. I haven’t done much of this at all in the past few years and I think my wardrobe has suffered as a result. I don’t realize that there is a wealth of outfit options in what I already have, so I think I have to go out and buy more in order to dress well, and the cycle continues. My recent challenge has showed me that I need to allocate the time to “play” in my closet to prove to myself that I have enough. I may learn that I only need a few strategic purchases rather than a lot of more of the same of what I already have. I suspect this will be the case and that these items will all be bottom pieces. That’s my guess, but I will have better knowledge of that through finishing this challenge, doing the exercise above, and doing a few outfit creation sessions over the next month or so.

Conclusion and Your Thoughts

I hope you found this post interesting even if you don’t share my particular wardrobe challenges and insights. I know that not all of you have done Project 333 or the 30 for 30 Remix, but you have probably gained knowledge about your wardrobe in various other ways. I’d love to get your feedback on this topic. Here are a few questions to help you gather your thoughts, but feel free to comment however you’d like.

  • What have you learned about your wardrobe and your style preferences from times when you needed to dress with less (i.e. travel, a closet challenge, or a body or lifestyle change)?
  • What “blind spots” have you discovered with your wardrobe and how did they impact the way you dressed and how you felt about your outfits?
  • What are your biggest fit challenges and how do they affect your wardrobe satisfaction?
  • What have been your greatest wardrobe challenges overall?
  • What wardrobe and style goals do you have for 2019?

I look forward to reading your thoughts on these questions (and they may inform future blog topics!).

Thank you for reading. I plan to publish another post before the end of the year, but today I would like to wish all those who celebrate a very Merry Christmas!

christmas pets

I hope that whatever the weather brings on the holiday and whoever you spend the day with, it is a joyous occasion for you. Many blessings to all of you, my dear readers! I appreciate your reading my words and sharing your insights with me.

12 thoughts on “Insights from My Fall Essential Wardrobe Challenge

  1. Tara C says:

    I’m really short and everything needs to be hemmed, but I have very little trouble finding pants that fit. My problems are usually not having enough special/interesting tops. I tend to find one style I really like and then buy too many of that same style, so I had to make myself a rule that I can now only buy two of any particular top. Also, since I stopped working and hardly go out, I end up wearing tshirts, jeans and tennis shoes 90% of the time, which leaves a large portion of my wardrobe unworn. Unlike you, my summer/winter clothes aren’t much different at all in San Diego, I just throw a hoodie sweatshirt on over my tshirt. Boring! My goal is to push myself to wear more of my clothes. I’ve worn the same jewelry for months as well. Part of that is grieving after the deaths of both my dogs this summer, but part of it is just laziness and apathy too. Who really cares what I look like, so why bother, is how I’ve been feeling. I’m hoping I can get out of my rut/funk in 2019.

    1. Debbie Roes says:

      I struggle with not having enough special and interesting tops, too, Tara. I love my stripes and feel happy wearing them, but I definitely have too many similar striped tops and would have done better buying different styles that would give me more variety. I think it’s a good rule to only buy a maximum of two of any particular top. I usually do that, but sometimes I lapse and end up being sorry that I did. I hear you on being in a style rut and feeling like why bother sometimes. I have that issue, too. In regards to having separate summer/winter clothes for San Diego, I probably could have a lot more crossover items than I do, but I have cultivated these distinct wardrobes that don’t play well with each other for the most part. This is something I want to work on… You have had a rough 2018, so it’s understandable that your style would take a back seat. I hope that 2019 will be a much better year for you in all respects. Have you chosen a word/theme for the year? That often helps me to get to a better place. I haven’t pinpointed my 2019 theme yet, but I will write about it in a few weeks.

  2. Katrina B says:

    If I look at wardrobe challenges over my entire life, the height/pant length far outweighs everything else. I could never get pants long enough when I was a very tall child and teenager, and I don’t seem to have grown out of that awkward and uncomfortable feeling of people making fun of my “flood pants”. Even now that it’s stylish to wear very short pants, I feel ridiculous with my hems at my ankles or above. This is one of the main reasons that during my huge closet purges over the last couple of years, I couldn’t seem to give up several pairs of jeans and pants that didn’t fit me due to some weight gain. They were the perfect length! I am so thankful that I kept all those jeans, because I can now wear them again and I saved myself hundreds of dollars and the frustration of searching all over again for brands that fit well and are long enough.

    It’s interesting about the blind spots. Maybe we can only see (haha) one at a time. It actually took me a couple of years to realize that I was very uncomfortable wearing the short sleeved rayon T shirts that I had thought I loved. The fact that I was wearing crisp button front shirts with 3/4 sleeves every time I left the house finally got through to me. Now I’m having some sort of epiphany about wearing columns of color rather than contrasting separates, but I haven’t yet worked out what that means for my wardrobe.

    I look forward to reading more about the results of your challenge.

    1. Debbie Roes says:

      Another tall woman! I nodded along while reading your first paragraph, Katrina. I have struggled to embrace cropped pants for the same reasons you mentioned. They just feel “wrong” on me, especially the ankle length ones that are reminiscent of my previous flood pants. I tend to hold on to too-small pants/jeans for a long time, too, even if I don’t love the style that much anymore. I always fear that I won’t be able to find good replacements and that is a valid concern! I’m glad you were able to fit into the old pants again and save yourself money and frustration. I have been hoping I could, too, but the menopausal weight gain is being very, very stubborn 😦

      Thanks for sharing your blind spot story. I think sometimes we buy stuff because it’s either trendy or someone else pushes us to do so. I have definitely had “what was I thinking?” moments about some things in my closet. I like the column of color look, too, and want to embrace it more. I think it’s a flattering look and I also like the simple and minimalist aesthetic. I think I need to spend more time finding style images that resonate for me and then trying to translate them in my closet. Doing this will help me to get out of the bit of a rut I’m in, plus it will help me to identify what I most need (in addition to the long enough pants/jeans!) so I can hopefully shop better (always the goal, isn’t it?).

      1. Katrina B says:

        I also should say that I plan to keep my larger jeans and pants from the “menopause years.” I have learned a few lessons (at almost 60 I should hope!) and one of them is that nothing is permanent. Changes in my health and the various medications I take could also impact my weight, so I might as well be prepared. This is not the popular minimalist mindset, but common sense takes precedence. Wow, I sound just like my mother! 😆

        1. Debbie Roes says:

          Well, minimalism is about having things that add value to our lives and for people who find it hard to find jeans and pants that fit, having some on hand in case of weight gain or loss sounds valuable to me 🙂 I don’t hold onto a lot of “just in case” clothes these days, but I have kept some of my too-small pants/jeans, as long as I can see myself realistically fitting into them again. I’m sure you have a lot of wisdom at almost 60, Katrina, and this is a good example. I sound like my mother a lot, too, as does my husband (like his mother, not mine lol). In fact, we have a notepad on our fridge with the saying, “Sometimes I open my mouth and my mother comes out.” Makes me grin every time I see it!

  3. Gail (Helen) says:

    So glad to have a post to read this a.m. by my favorite blogger. I have noticed I am happier on a trip, having even less to choose from than my 30-40 total pieces at home. I make sure to pack so that everything goes together. I wear the same things all year except for a few–coat, thick cardigan, fleece. It is very hot here in summer and for a long time, but I did find a blind spot through my being cold in air conditioned spaces as well as in winter. I needed warmth and have found it through an under layer of tank tops in addition to the usual toppers.
    I am barely a petite–5 feet 3.5–and have trouble with pant length, but found L.L.Bean petites work. (I hate sewing.) I also cannot stand to wear jeans or nylon pantyhose and have feet that require orthotics and a big toe box. So there are clothes choice limits, but as I am 72, who cares! I prefer simplicity, classics, small wardrobes, but I LOVE reading about others’ preferences and solutions, esp. when well-written and forthright as in FLR.

    1. Debbie Roes says:

      I’m proud to be your favorite blogger, Gail 🙂 I’m happier on a trip, too, especially if I pack wisely. Even when I didn’t do the best packing job last April/May on a trip to see my family, I still appreciated the simplicity of dressing with less. Interesting that you also feel this way even though you already have a very minimalist wardrobe. I think I crave simplicity but because of certain neuroses I have, I haven’t been able to “get there” with my wardrobe just yet. Hope springs eternal, though, so I’m going to keep working on it!

      Good for you for discovering a blind spot and working to correct it. I love that you have a “who cares” attitude about your clothes choice limitations now. I’m not there yet, but I hope that will come with time and age. I have read that the 50’s are when women stop caring so much about the opinions of others and follow the beat of their own drummer more. I’m still in my early 50’s, so I’m hoping that comes for me, too. We’re the ones who have to live our lives, so it’s always our own opinions that should matter most! Thanks as always for your support and kind words 🙂

  4. Sam says:

    Just wanted to tell you you’re my favourite blogger too, and I’m sure Gail and I are not alone in this! It’s the way you write and convey your emotions and insights. And the photos you used to take – I have even printed a sunset of yours and hung it in my living room. I want to thank you for sharing your talent and wish you and your readers a lovely Christmas.

    1. Debbie Roes says:

      Thank you so much, Sam! The kind words from you and Gail were especially meaningful to me now because I’ve had a rough few days. I’m so touched that you printed my sunset photo and hung it in your living room! I plan to start posting photos from time to time again. I haven’t been taking them as much lately, but I miss it. I got a bit overwhelmed with the quantity of photos I already had, but that’s kind of a separate issue from the enjoyment I get from taking them! I have read of others who just save one or a few photos from each session and I like that idea 🙂 Merry Christmas to you, too, and I wish you many beautiful sunsets.

  5. jenn says:

    I’ve learned that when I travel, I don’t need much variety. We drive to Florida each year (from Michigan) so we can take our dog with us. I dress for comfort in the car. Knit pants. A light-weight sweatshirt. Last year, I took very few items to wear at our destination and still never wore a couple of the tops. We only stay for a week, and warm-weather clothing doesn’t take up much room, so I’m pleased with the amount I took.

    Blind spots, hmm. I probably have many. One problem is, sometimes it seems I forget that I’m retired (almost five years), and I’ll buy a woven blazer in a pretty color that I’ll only wear because I feel I need to. Not because I want to. Like you, I want my clothes to “give,” and I rarely dress up. I also have way more outfits for every type of activity that I need—except funerals—because I look deathly in black (pardon the pun). I’m in the process of figuring out just how many outfits I have. I’ve written out potential (winter) combos. My plan is to start getting ready for events way ahead of time, so I can try things on and determine if and how I want to wear the items I own. If I don’t love an item in any outfit, and it’s not something I can use around the house, it’s going out the door.

    I also want to purchase less items than I get rid of and be more intentional with those purchases.

    Those are just a couple of the resolutions I’m taking on for next year with my own Happiness Project.

    Fit challenges for me are a long torso, short (but not petite-short) legs, and virtually no shoulders.

    Unlike you, I have succumbed to the deals offered over the past few weeks. The perfect jeans, the perfect black pants… It’s sickening to think of all the returns I have to make. I’m quite selective until I get worn down and tired from all the trying on, deciding, returning… it’s a time-sucking cycle I intend to break in 2019.
    On a lighter note, Merry Christmas, Debbie. I look forward to learning more from you in the New Year.

    1. Debbie Roes says:

      I feel the same about travel, Jenn. I always THINK I will want lots of choices, but then I’m okay with just wearing a handful of favorites. Perhaps I should be taking the lesson from that! I get what you’re saying about your woven blazer and wearing it because you feel you need to. That has happened to me many times, but I’m doing better now at buying things that are a match for my casual lifestyle. I’m going to do the same thing as you with my “winter” outfits (in quotes because we don’t get true winters here). I did that for summer and it was very helpful. I was amazed at how many combinations I had. Some of them I didn’t end up loving when I wore them all day long, but I still had a lot of choices. Getting ready for events long ahead of time helps a lot, too. I did that with my brother’s wedding in August and my outfit ended up being pretty good.

      Try not to be too hard on yourself for succumbing to the deals. Hopefully at least some of your purchases will work out, but I understand the frustration with dealing with all of the returns (that was the case for me with NAS). I intend to break the buy/return cycle in 2019, too, so perhaps we can help each other. Wishing you a Merry Christmas, too! I hope to post more often in the New Year than I have the past few months.

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