My Wardrobe, Myself

The intersection of clothing, emotions, and life

Last week, I wrote about my shoes in the first installment of my periodic “Rule of Ten” series. I decided to split my footwear into two Rule of Ten collections: one for my summer shoes and the other for my “not summer” shoes (for the cooler months of the year). While I could have selected ten pairs of shoes for each collection, I only wanted to include the footwear that I love and wear regularly. Therefore, I chose only seven pairs of shoes each for the summer and “not summer” seasons.  I also shared my reasons for making these Rule of Ten selections and speculated on the types of footwear I might be interested in purchasing in the future.

As I mentioned in my last essay, I don’t want to make new shoe purchases while so much of my existing footwear (14 pairs!) is still “on the bubble.” I’d like to make concrete decisions about each of my “maybe” shoes so that I can do one of three things:

  • Start wearing them regularly
  • List them for sale online
  • Pass them on via donation

Today’s post kicks off that decision process. I look at the six pairs of shoes that didn’t make the cut for my “not summer” Rule of Ten collection. I explore my feelings regarding these cool weather shoes and highlight why I didn’t feel right including them among my favorites. I then let you know what I plan to do in order to make up my mind about each pair of shoes in the near future.

deciding on shoes to keep or purge

Sometimes it’s difficult to know which shoes to keep – and which to purge. 

I decided to begin with this group of shoes (which I’ll show below), as the cooler weather “season” will be wrapping up in another month or so (it typically lasts from December through June).  I’ll address the eight pairs of shoes that I didn’t include in my summer Rule of Ten collection in a few weeks.

A Few Words About Numbers…

Before I delve into my shoes that are “on the bubble,” I’d like to share some thoughts about numbers. A few readers questioned my decision to have two separate Rule of Ten footwear collections, as they themselves easily get by with fewer than ten total pairs of shoes (and some even have fewer than five pairs!). While I’ve become more minimalist in many areas of my life, my wardrobe is one area in which I’m still more of a “maximalist,” although not nearly as much as I used to be.

That being said, I do want to pare down my closet – and also decrease “closet churn,” which is a big part of why I created the Rule of Ten and am writing these posts. While it’s possible that I may eventually be happy with only ten total footwear options, that’s not what I’m choosing today. As someone who owned over fifty pairs of shoes for many years, I’d be quite satisfied to get down to twenty or fewer pairs this year – and maintain that level.

There is no one right number of shoes – or any other type of wardrobe item – that a person should own. It’s a very individual decision and is dependent on many factors. For some people, clothing and shoes are just basic necessities that are decided upon for purely practical reasons. But there are many others who enjoy the creativity of putting outfits together and using clothing as a means of self-expression.

While it’s definitely possible to be creative with a smaller number of pieces, many people like to have a wider array of options from which to choose. That’s true for me, but I also don’t want to hold on to items that I’m not using, as that can become overwhelming. Many of the shoes in my closet are simply gathering dust, so I’d like to either have them become part of my working wardrobe – or sell or donate them so that someone else can hopefully use them.

“Not Summer” Shoes that are On the Bubble

I classified the six pairs of “maybe” shoes below as “not summer” options, as they either have a closed toe or a peep-toe.

cool weather shoes that are on the bubble

I’m not sure whether to keep or purge these six pairs of cool weather shoes. 

These shoes are less-open forms of footwear than what I wear during the warmer months. I realize that they’re likely more open than what many of you wear from December through June (at least in the northern hemisphere), but it doesn’t get that cold where I live. Therefore, I often wear both closed-toe and peep-toe shoes in the cooler months, and my feet are usually warm enough. If I’m going to be outdoors for a longer time period, I’ll generally reach for closed-toe footwear worn with socks, but that’s not how I spend most of my days.

I’ll go through the above shoes one by one to explore why they weren’t included among my favorites and what I plan to do next to get them out of “limbo land.” So that you don’t need to keep scrolling up to the picture above, I’ll include a photo of each pair of shoes in the appropriate section.

Black Ecco Chelsea Booties

black Ecco Chelsea booties

These boots are ten years old! I actually gave them away at a 2017 clothing swap, but I got them back a year later when my friend decided she no longer wanted them. I thought that perhaps I’d enjoy wearing these boots again, but that hasn’t really happened. My main reason for taking the boots back is because they’re very comfortable and I can walk in them for long distances. In fact, I purchased them in Las Vegas when the boots I had been wearing there gave me some pretty extreme blisters (if you’ve ever been to Vegas, you know that extensive walking is the name of the game in that town).

Comfort is always a big plus, but there are two main issues with these boots. The first is that I usually choose to wear my other two pairs of black booties (shown below at center and right) instead of the Ecco Chelsea boots, as I prefer those styles (they were both included in my not summer Rule of Ten).

my three pairs of black ankle booties

My three pairs of black ankle booties – I prefer the style of the second and third pairs. 

The second issue is that these boots pair best with either boot-cut or wide-leg pants/jeans because of their wider opening. Back in 2011 when I purchased the boots, my pants all had wider hems, but now I mostly wear a narrower straight-leg style.

In order to make a decision about these boots, I need to try them on with all of my pants. If any of my pants work well with the boots (hopefully at least one or two will), I’ll wear the combination at least once to see how I feel – and if I might potentially reach for this shoe option over others, especially in situations when I might be doing a lot of walking.

If I don’t have any good pant options for the boots, I still might hold on to them for the comfort factor, especially since wider-hemmed pants are becoming more popular again (and I’m likely to embrace that silhouette). But the bottom line is that I’d like to make a decision about the boots – and all of my “on the bubble” shoes – by the end of the year, if not much sooner.

Black Gentle Souls Cross-Strap Wedges

black Gentle Souls cross-strap low wedges

I purchased these shoes in 2018 because I liked the style and they felt comfortable on my frequently fussy feet. I still like the style, but I’m not sure if I like the way the shoes look on me and with the types of outfits I wear. I often put these shoes on, only to remove them shortly thereafter and choose an alternate footwear option. I’m not exactly sure why I do this, but that’s something I need to figure out.

These shoes have a small wedge heel, which is in line with my preferences. I generally opt for heels instead of flats when wearing pants or jeans, as I like the slimming effect the elevated height creates (yes, even with my tall stature!). Although I appreciate the look of flats with pants on other women, I often feel frumpy and bottom-heavy when I wear that combination myself. I’ve been trying to get past this perception for the sake of increased comfort, but it’s still a struggle for me. Interestingly, I can embrace certain styles of lower-heeled sandals with pants, but I’m not as keen on the closed-toe options for some reason.

Maybe the heel on these shoes is too low for me, or perhaps the silhouette is different enough that my eye hasn’t sufficiently adjusted. In either case, it’s frustrating to own shoes that I ostensibly like and not know how to make them work in my wardrobe. Maybe I haven’t tried hard enough, though. I’ve mostly stayed in my comfort zone wearing the same few pairs of shoes over and over again, and these cute shoes have gotten lost in the shuffle.

Since I like these shoes and they’re comfortable, I’m going to push myself to wear them soon. I’ll figure out some potential ways to wear them that I hadn’t previously considered. Perhaps I’ll try pairing them with a dress instead of pants – or maybe with different pants than I’ve tried in the past. If you have any suggestions as to how to wear this type of footwear, please share them, as I’d love to make these shoes part of my regular rotation.

I used to “play” in my closet on a regular basis, putting outfits together and taking photos to remember the combinations I liked the most. I haven’t done much of this for years, which is part of why some of my wardrobe pieces have become orphans. Because I’m unsure how to wear some of my closet items, I primarily stick with the “tried and true” when getting dressed. If I want to incorporate some of my less worn pieces into my regular repertoire, I need to put a little work into styling them.

Black Vince Camuto Lavette Peep-Toes

black Vince Camuto Lavette booties

I picked up these shoes at a local consignment store in February 2020 and never got around to wearing them prior to the pandemic and shelter-in-place orders. When I had an opportunity to include them in an outfit not long ago, I discovered that they weren’t as comfortable as I thought during my simple try-on at the store. I have very high arches and insteps, so shoes often fit snugly at the top of my feet, which was the case with these peep-toes. My husband put them on a shoe-stretcher a couple of times and they fit better now, but I’m not sure if the heel height is manageable for me.

I used to love wearing higher heels, but now my upper limit is two inches – or maybe two-and-a-half, and these have a three-inch heel. I’ve hesitated to wear them because I didn’t want to be stuck out and about with uncomfortable feet, but I need to figure out if these shoes will work for me – or not. I love the style, but I’m committed to no longer owning any “sitting shoes.” I’m going to try wearing these shoes soon for a quick outing to see if they can be worn without discomfort. If my feet hurt, the shoes won’t get to stay in my closet!

Black White Mountain Peep-toe Mary Janes

black White Mountain peep-toe Mary Janes

These shoes are even older than the Ecco booties I wrote about above! I bought them in April 2011, and I’ve worn them many times over the years. However, they fell out of my favor a few years ago when I purchased new options that better fit my current style aesthetic, including the ones featured in my post last week.

In the past few years, these shoes haven’t left my closet much. I no longer track wears, but I think I’ve only worn them a handful of times in recent years. I’ve mostly hung on to them because they’re comfortable and used to be a favorite of mine. I have a hard time letting go of comfortable shoes because it’s difficult to find options that don’t hurt my feet in one way or another. However, these peep-toes are less than pristine at this point – and even though they’re still technically wearable, I always seem to choose something else instead. Now that I’m thinking about it, perhaps the black Gentle Souls wedges I covered above might work for outfits in which I used to wear the White Mountain peep-toes. I’m going to experiment and see if that possible substitution is a valid option.

Taking the time to go through my shoes has helped me decide to let this pair go. I don’t love and wear them anymore, so why hang on to them? I’m going to donate these shoes soon, along with some other closet items that I’ve culled over the past month or so. The Rule of 10 exercise is helping me determine which pieces I like most, which is making it easier to let go of lesser-loved items.

Metallic Gentle Souls Cross-Strap Peep-toe Wedges

metallic Gentle Souls peep-toe wedges

I purchased these shoes around the same time as the closed-toe black pair I wrote about earlier, and they’ve been equally challenging for me to style. I’ve worn them, but not very often, and their mostly “benchwarmer” status can be attributed to the same reasons. I just don’t know how to wear them in a way that feels right to me. Again, I need to spend time doing a bit of experimentation, and I have yet to make that a priority. Once in a while, I’ll put these shoes on with a given outfit, but I usually take them off because the combination looks wrong or I feel frumpy.

I don’t think the shoes look frumpy and I still like the style, so maybe there’s hope for them yet. But I don’t want to keep them around if I’m not going to wear them. I want the items in my closet to earn their keep, even if everything isn’t worn equally as often. As with the black Gentle Souls shoes, I’m open to suggestions for how to wear this shoe option. What would you pair them with? Maybe I need to think outside the box a bit more…

Navy Faux Suede Arcopedico Booties

navy faux suede Arcopedico booties

These boots were given to me by my mom just days before the pandemic shutdown occurred. She was visiting me and we did some shoe shopping together. My mom has fussier feet than mine and lives in a place (Tahoe) where there aren’t many good shopping locations, so she often wants to look for comfortable and cute shoes when she’s in town.

While we were in my mom’s favorite shoe store, I tried these boots on and commented that they felt like slippers on my feet. I didn’t own any blue footwear, so my mom offered to purchase the boots for me. I was excited to wear them, but then we all know what happened next… The lockdowns occurred and I wore only athletic shoes and slippers for months on end! I haven’t had many out-and-about occasions during the cooler months, but I know that I could have worn these boots at least a couple of times and didn’t. I’ve typically stuck with my standard black or metallic footwear when I’ve ventured out and haven’t tested out other options.

As with some of the other shoes covered in this essay, I need to figure out what to pair these shoes with. See a pattern here? When I don’t take the time to experiment in my closet and do outfit creation, I just stick with the same “tried and true” options over and over again. I know I have clothes that I can wear with these navy boots, but given my overall mood and energy level during the pandemic, I’ve taken the easy route when putting my outfits together. I’ve worn the clothes and shoes that I knew worked for me and left the more challenging or problematic options alone.

I’m not going to beat myself up for sticking with my proven footwear favorites in recent months, as it’s been a difficult time for all of us. It’s only natural that outfit creation and dressing our best has taken a back seat, especially since we’ve mostly been at home for the past year-plus. But now that we’re beginning to see light at the end of the tunnel, I’m feeling more in the mood to up my style quotient and make decisions about what to keep and what to purge in my closet.


So, there you have it… I looked at the six pairs of cool weather shoes that weren’t included in my Rule of Ten collection for that time of year. I explored why those shoes didn’t make the cut, and I created a plan for how to make concrete decisions about them in the near future. Now I just need to execute that plan, which I intend to do before the summer season arrives. I don’t want these shoes to continue gathering dust in my closet for another five or six months until it’s seasonally appropriate to wear them again. If I decide they’re not going to serve my sartorial and stylistic needs, I’d rather move them along as soon as possible so that someone else can hopefully enjoy wearing them.

As you can see, it’s not easy for me to let go of shoes. The ones I opt to pass on are usually uncomfortable, worn out, or totally not my style anymore, which doesn’t apply to most of the shoes I wrote about above. I guess the bottom line, though, is that if I have to talk myself into keeping something, I should probably recognize that I have other footwear options that better fit my current lifestyle and style preferences – and it’s time to pass the item in question on.

I don’t want to be under the illusion that I have more footwear options than I actually do just because I have a lot of shoes in my closet. I want everything I own to be worn on a regular basis, with the rare exception of a few formal-wear items. This applies not just to shoes, but also to clothes and accessories, some of which I’ll address in future Rule of Ten posts. This was a good place for me to start, however, and I believe that I gained valuable insights through engaging in this exploration. I’ll update you on my shoe decisions in a future essay, and I’ll continue to share more Rule of Ten collections and “on the bubble” item reviews in the coming weeks and months.

Your Thoughts?

Even though this essay focused only on my shoe collection and personal opinions, I hope you still found it interesting and helpful. Sometimes reading about how another person thinks about things and the insights they’ve gained can help us better understand our own challenges. You may have very different issues with your footwear than I do, or you may not struggle with letting go of shoes at all, but hopefully you still benefitted from reading my process.

I’d love for you to weigh in on this post. Here are a few questions for you to answer, if you’d like:

  • If you have shoes that are “on the bubble,” what do you see as the reasons for that situation?
  • What do you plan to do to make a decision, one way or another?
  • Do you enjoy these wardrobe review types of posts?
  • What other types of posts would you like for me to do?

I welcome any thoughts and insights you want to share, whether it’s about my footwear issues, your own shoe challenges, or the future of this blog.

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29 thoughts on “Addressing “On the Bubble” Shoes – Not Summer Edition

  1. Vildy says:

    I do enjoy analytical posts like this. I’m wondering if the metallic wedges would look fine with pants because of the bit of contrast but it’s sister black pair might create a heavy look under dark pants because of the wedge style. Somehow seeing the separation between forefoot and and heels creates more energy and looks less clunky. Even though the actual shoes on their own aren’t particularly clunky. So I think with the black ones you need to see the skin on the top of your foot and they should work well with skirts and dresses.

    Glad you came to the decision to get rid of the worn out mary jane flats. Comfortable is a big draw and hopefully your remaining shoe wardrobe will
    provide you with exactly that. The other day in the thriftstore I along with other oldsters were talking about breaking in shoes. It used to be every shoe
    but now we want our shoes to feel comfortable right away. And that’s great but also the more you wear leather shoes the more they should start to
    conform more and more to your own foot and gait. In the meantime, I’m guessing the Ecco super comfortable shoes could be your version of hiking boots. 😀 Though sadly they’re probably not doing your total look any favors vs your sleeker looking boots.

    1. Debbie Roes says:

      Thanks so much for your prompt and helpful comment, Vildy! What you wrote about needing to see the separation between forefoot and heels makes good sense and was a “light-bulb moment” for me. I will try the black wedges with skirts and dresses to see if I might like that look better. I also think the peep-toe of the metallic pair breaks up the look a bit, but I agree about the contrast of the color with the dark pants that I usually wear.

      I completely agree about wanting shoes to be comfortable right away! I guess I’m an “oldster” now, too, lol. Yes, the black Ecco boots are not as stylistically pleasing as my other boots, and I wouldn’t have kept them at all if it weren’t for their extreme comfort. Good idea to consider them more like “gear” for those days when I’m going to be walking a lot and don’t want to wear sneakers. They’re a step above wearing sneakers with a “regular outfit,” but they’re certainly not up to my usual style standards.

  2. NATALIE K says:

    Debbie, It helps me see how you think through exiting something from your closet. I recently read your article on finding a hobby. All so true!! I need to actually add a few flats, but otherwise I feel pretty good about my shoes. I’ve decided if I don’t wear my clogs this winter, I may need to slim those down a bit. I now will be able to really think through how I feel about each shoe. They are all such investments.

    1. Debbie Roes says:

      It’s great to hear that you’re reading and liking my old posts, Natalie. That’s great that you feel like you’re in a pretty good place with your shoes. Yes, it’s a good test to see if you wear shoes during their appropriate season. Shoes can definitely be a big investment, but if they’re not working for us for whatever reason, we sometimes need to let them go. Good luck with the further evolution of your shoe wardrobe.

  3. Thanks for sharing how you are working through these decisions. Whether a person is curating a closet of 6 pairs of shoes, or 26, or 206, analyzing whether the shoes are a good component of that wardrobe is important.

    The cross strap wedges are very cute. I think the black ones could work well with a skirt/dress. With pants is a definite possibility, but they might need to be an ankle or cropped style or a rolled up skinny pair. A full-length pair with the straps doesn’t feel right. For me (in Minnesota) that is definitely a warm weather shoe. I don’t wear sandals at all. I wonder whether that style of shoe fits a niche for you, if you prefer boots and sandals.

    This is a tangential comment, but your discussion of not knowing how to style certain items you buy made me wonder whether something I’ve always thought of as a normal part of purchasing and deciding to keep items is not as common. When I get something new, I make a point as soon as possible (at the latest, the first weekend I get to after the purchase) of trying it on with the things in my closet that I have expected it to work with as well as other things in my closet to make sure it is going to be a functional part of my wardrobe. Then if it doesn’t actually work with what I have, I can either send it back (this should be the outcome most of the time) or, if I love it on but need something else to make it fit in, I can decide to work with that and prioritize identifying and buying the missing piece (this should be the outcome in very rare cases).

    I own too much, but I don’t tend to have things that I don’t wear because I try to approach things on a wardrobe level and don’t keep things that don’t work with the wardrobe over all. (My problem is that it’s SO easy to incorporate new things into my wardrobe that this doesn’t act as much of a barrier these days!)

    It’s funny, I think I got in the habit of doing an immediate outfit creation session with new purchases when I was growing up and getting something new was a relatively rare event due to finances. It was just so exciting to have new things that I was eager to start trying them out, and the idea of keeping something I wouldn’t happily start wearing right away…that would not have computed for me because that item should go back to the store so I could get something different that I would love.

    1. Vildy says:

      I really like Sally’s idea of using cropped or rolled pants with the black cross strap wedges and showing some skin that way, though in your specific case I think I remember your past frustrations at finding full length pants at your height. So you might not have much in the way of cropped pants.

    2. Debbie Roes says:

      I really appreciate your feedback, Sally! I agree that the cross-strap shoes probably wouldn’t work so well with full-length pants, or at least the best feature of these shoes wouldn’t be visible in that instant. While I avoided cropped pants for a long time (to Vildy’s point) because I associated them with the “floods” of my youth, I have embraced that style in recent years and now have a decent amount in my closet. I will try the shoes with cropped pants and see what I think.

      Your practice of styling new items immediately upon getting them home makes good sense, and I usually do that type of thing NOW. However, when I bought many of the shoes I wrote about, I didn’t engage in such a practice, to my detriment. I think I was much better about doing it with CLOTHES and I mistakenly thought that shoes would work as long as I liked the style and they were comfortable. I think it’s not necessarily a common thing for women to style new items, as when I used to do wardrobe consulting, I found a lot of unworn items in my clients’ closets. A lot of people never return anything! I return a lot, but clearly not enough sometimes…

  4. Gail says:

    Always yor posts are interesting, Debbie.
    Iused to buy shoes that seemed to have good archsupport without myorthotics (I have metatarsalgia). They never were good enough once I regularly tried to wear them. I have learned to buy ony those shoes that accommodate my orthotics. Big lesson learned, but I do not always like the looks of the shoes. As hard as it is to see money spent on shoes that do not work, it is a great feeling to donate and to learn, finally, how to select new shoes.

    1. Debbie Roes says:

      Metatarsalgia sounds painful, Gail. I remember having a friend with that problem and she was pretty miserable sometimes. My mom wears orthotics in her shoes (for a different issue), so I know it can be challenging to find attractive shoes that accommodate them. I think it’s getting at least somewhat easier these days, but there are still a lot of shoes that people who wear orthotics have to pass up. You have a good attitude about donating and learning, which is great.

  5. Murphy says:

    I really like your point that you don’t want the illusion that you have more footwear options than you actually do just because there are a lot of shoes in your closet. I always have a hard time getting ready to go out of the house because I frequently end up changing out of the shoes I thought would go with my outfit. This week I made some progress towards figuring out why I don’t wear certain shoes. I just donated 3 pairs of shoes that I loved the look of, but when I tried to wear them for a even a short time they hurt my feet. I just took them right to Goodwill before I had time to change my mind. I suspect that a few more pairs will be following soon if I am realistic. I think I need to try on outfits and see what shoes I need to make my favorite items work, like Sally suggested up thread – that’s a great idea in general!

    1. Debbie Roes says:

      Congrats on the progress you made this week with your shoes, Murphy! I’m glad you got rid of shoes that hurt your feet, and good for you for taking them to Goodwill right away before you changed your mind. It’s not in our best interest to hold on to uncomfortable shoes, no matter how cute they are or how much they cost. Good luck with going through the rest of your shoes! I agree that Sally’s advice is something we should all follow.

  6. Maggie says:

    HI Debbie,
    I have just moved to another state and I have been wearing the same things for one month. (Everything else is still in storage.)
    So, I discovered the thing that I missed most was my robe – I guess the comfort factor.

    My spouse and I are in a short-term apartment while we find a house to rent.

    I brought my favorite cashmere sweater, fleece jacket, 3 pairs of pants/jeans and one set of loungewear.and half a dozen tees.

    I happened to go into a Goodwill and it was really nice in there. It was clean and clothes were on racks by type, size, and color.
    For example, one rack had short sleeved shirts in size S that were blue to green.

    Last week, I ended up with a pair of jeans, a lounge shirt and a print tee. I bought two more cashmere sweaters on Ebay and Poshmark in a style similar to my favorite sweater.

    I am trying a new shopping pattern.

    I am going to try and just buy prints and clothes that I think are “happy” at Goodwill and see how that meets my needs to have something new for the season and other things I will just keep buying my basics/classics.

    I have replace Ecco boots on Ebay that I have actually worn out. You can always change the color of shoes – I think you changed a pair of sandals to cobalt blue once?

    As to your shoe wardrobe, the ones from gentle soles look a little more feminine to me – like ballet slippers. I would think that they would look better with dresses or prints or maybe more of a nude color would work with summer stuff? Colorblocking could be interesting too.

    (I have definitely found that my mood is related to the comfort of my shoes and the padding in my insoles so I have high expectations in this area.)

    I will keep you posted on my Goodwill experiment.


    1. Maggie says:

      Hi Debbie – I forgot to mention that I brought my four favorite pair of shoes to my temporary digs.
      They are: Ecco Sense black toggle shoes (full price at Ecco)
      Ecco Goretex high ankle hiking boots (first pair was full price at Ecco years ago – since them replaced twice on Ebay with pair in better shape.)
      Hush Puppies Women’s Cyra Catelyn Chukka Boot (ankle boot in waterproof suede – olive brownish color) Originally bought these in gray from DSW and liked them so much I bought another pair in same size but different color on Ebay.
      Merrell Ortholite Mary Jane slip on slides with adjustable strap – black suede I think (these often work as sort of slippers since I can slide them on and off as needed.) These were bought at Savers Thrift Store in New Hampshire.I like them because I have a narrow foot and I can adjust the strap agross the top so the shoes don’t slide.

      I probably have 2 pairs that I wear infrequently (I think – my other shoes are all in storage at the moment!)
      One pair are Ecco Soft 7 in a light blue print. (Very comfortable but not water resistant in New England weather and not in my usual color palette.)
      The other pair is a pair of brown suede zip ankle boots with a maybe 1-1 1/2 inch heel? I wear these for dress up only or when I want a little height.

      I have discovered with shoes that I do best when I go and just try on for fit and comfort. If they work out, I can always return them and get a different color somewhere else.

      Also, I do have my insoles for high arches in all of my shoes.


      1. Maggie says:

        FYI – Inside Out Style blog by Imogen Lamport has a great article titled, “What You Need to Know About Choosing Shoes to Go With Your Pants.” (Also, sometimes it is easier to wear a specific article pants/skirt on the bottom if you are looking for ideas while shoe shopping.)

    2. Debbie Roes says:

      Thanks for your comments, Maggie. Dressing with a smaller number of items, as you’re doing in light of your move, can helps us to better understand what we like and what we need. That’s a great idea to use Goodwill for trying out new patterns and styles. Also great that you were able to find cashmere sweaters on eBay and Poshmark.

      You have a good memory about my changing the color of my sandals! I did dye a pair of light blue sandals to more of a cobalt blue (it actually turned out more teal, but it was still a better color for me). I sold those shoes late last year because they weren’t as comfortable and versatile as I’d hoped, but I would be open to dyeing shoes again. Maybe dyeing my worn out pair of Ecco wedge booties (shown in last week’s post) would help me to get more wear out of them. I may look into that soon. You’re right that the Gentle Souls shoes are more feminine than what I usually wear. Maybe that’s part of why I’ve struggled with them, but it makes sense that I might like them better with dresses.

      It sounds like you have some great shoes that are serving you well. I think that many of us mostly wear a small number of shoes most of the time, even if we have a much larger selection. Interesting that you have insoles for your high arches. Maybe that’s something I should look into…

      I will check out Imogen’s post on choosing shoes to go with pants. She always have a lot of helpful information, so I look forward to reading what she has to say.

      1. Maggie says:

        Hi Debbie, I just wanted to add that if I had the navy suede booties, I would wear them with jeans.
        As to dying a pair of shoes from black to another color, you can always dye them black again!

        1. Debbie Roes says:

          I agree that the navy suede booties would work well with jeans, Maggie. I also think that dyeing my less than pristine black wedge booties (that I covered in my last post) might help to give them some more life. Since it will be their off-season soon, I’m going to look into that option to see if it would be worth doing.

  7. Katrina B says:

    Very interesting, as always. Your essays always make me look at my own processes in a new light. After mulling things over since your last shoe post, I realized that I actually have a pretty organized approach now. Somewhere between the time decades ago when I had 50+ pairs of shoes in every style and color, and today when I have just 21 pairs, I started actually planning my wardrobe (thanks to Recovering Shopaholic as well as others!). This included narrowing down to a small color palette, as we discussed before, and defining outfit silhouettes. Once I determined there were really only 3 different silhouettes I wore, I realized I only needed a few types of shoes. No more boots, espadrilles, strappy sandals, slides, or ballet flats. Using a matrix of 4 neutral colors and 4 shoe styles (dressy flat or low heel, casual flat, sandal, and “fashion sneaker”) I identified the 16 pairs of shoes that would match up with every possible outfit. Of course I already had many that fit right into the matrix, but for the others it was a while before I could find that rare combination of style and comfort. Eventually I did complete this “collection,” and it is basically what I have today. My total of 21 pairs includes those those pairs that could be considered duplicates but I just think of them as backup for when the primary pair wears out.

    Of course at some point I need to do a reality check both on shoes and clothes, because life now is quite different from life when I did my wardrobe planning.

    If you find a good way to wear those beautiful shoes with the crossed ankle straps, please share. My only experience with a shoe with a high ankle strap was a leather version with a single strap that, lacking any stretch, cut into my ankle. Your shoes with the stretchy ankle straps look like they would be much more comfortable.

    1. Debbie Roes says:

      This is great, Katrina! I love that you figured out the shoe silhouettes that you like to wear and purchased those styles in a few colors that work with your wardrobe. I’m kind of doing the same thing now, but I still have a bunch of shoes left over from before that I’m not sure what to do with, which is why I’m doing these posts. I haven’t gotten it all down to such a fine science as what you’ve done with just three main silhouettes, but I’m inspired by your process. Maybe I will try to see if I can come up with the same type of matrix as you described (with my main silhouettes) and see how it works out. Perhaps this will be a future post!

      The crossed ankle strap shoes are very comfortable, especially the black ones. The straps on the metallic shoes are a bit snugger, but I suspect they will loosen up with wear. The stretch is key, as I’ve struggled with ankle strap shoes, too, as I have bony ankles. I’ve gotten some good advice here, so I’m going to try the suggestions and hopefully make the shoes work. I will definitely do a later update on my shoes.

  8. NATALIE K says:

    Debbie, I am quite surprised that you didn’t style your shoes right away. I thought everyone did that! I always have… but then I thought about it… When I was taken shopping with my Grandmother and mother, that’s what I was taught to do. Plus, we bought clothing that would mix and match. If you’ll start stying every new item you bring into your closet, I think you’ll find you have so many more outfits than you think. Have you ever had someone make clothing personally for you? I’m considering this and I just would like to know how it worked out for you. Thank you!

    1. Debbie Roes says:

      It’s great that your mother and grandmother taught you smart shopping habits, Natalie. I’m sure that’s served you well over the years. I’ve never had clothing personally made for me, but there was a guest post on Recovering Shopaholic about that topic that you might find helpful:

  9. Gail says:

    Is it just my Ipad, or are others having trouble commenting because of a tiny, one-line space in which to type. I cannot even see what I have written clearly, and corrections(which I need!) are very difficult since I can’t see where they need to be made. It wasn’t like this before.

    1. Debbie Roes says:

      Sorry to hear that you’re having trouble with commenting, Gail. I haven’t made any changes to the site and the comment box still appears the same as usual for me, so I suspect that it might be an issue with your iPad. Maybe try a different device and see if you are better able to comment?

  10. Jenn says:

    This hasn’t been as burdensome as it sounds, but I’ve tracked all my clothing and shoe purchases for nearly twenty years. I’ve also tracked wearings. Lately, I’ve taken a serious look at any Spring/Summer items that I haven’t reached for and am intentionally wearing them. Doing so has helped me eliminate 16 items, 3 of which were (uncomfortable) shoes.

    As for new purchases, I’m buying primarily from places with generous return policies and trying out items when I receive them to see how versatile they are for my wardrobe. If I don’t love the item and it doesn’t work with at least three other pieces, it’s going back.

    1. Debbie Roes says:

      Wow, Jenn, you have such an amazing wealth of data at your disposal! I tracked wears for eight years and I learned a lot from it. I think we often believe that we wear things far more often than we actually do. That’s great that you were able to let go of 16 items, including 3 pairs of uncomfortable shoes. That must be a relief to you. Like you, I mostly buy from places with good return policies. I found that many of my mistake purchases were bought secondhand or final sale, so I don’t do much of that anymore.

  11. RoseAG says:

    Unless you think your Mother will mind I think I’d sell those Navy booties. They seem to be hardly worn and outside of your established shoe colors. Being new and hardly worn is probably a plus for them on the resale market.

    I think you make a good case for going through ones’ closet and making up outfits. It’s been more than a year since a lot of our outfits have had a chance to be worn and it’s probably time to be reminding ourselves of what we could be wearing.

    1. Debbie Roes says:

      I haven’t worn those booties at all yet, Rose. It’s true that they’re out of my established shoe colors, but navy coordinates well with lots of colors. But you have a point… if I’m not wearing them, it might be worth selling them. Time will tell! Yes, taking the time to put outfits together serves us very well, especially with new items and at the beginning of a season. I also find that the less often I “get dressed” (in “regular” clothes), the more out of practice I get with the whole thing. That explains at least some of why I’ve been less creative and imaginative in what I wear as of late. I definitely need to set aside some time for outfit creation soon.

  12. Cathie Perkins says:

    Debbie, I bought my first pair of archepedico boots a number of years ago and have bought 3 more pairs since. I live in a similar climate to you and these are totally fine throughout winter. Comfortable enough to wear all day. Have used them in Europe in winter as my main travel shoe and regularly walk 10km a day in them. So comfortable, seriously like socks with supportive sole. The navy will be great with jeans. You can also throw them in the washing machine and they come up like new. I always look at the end of season for sale boots for the next year. They are quite expensive in Australia but I think worth it.

    1. Debbie Roes says:

      Thanks for sharing your experience with Arcopedico boots, Cathie. I’m glad they’ve worked so well for you at home and for travel. Being able to walk for 10 km a day in non-athletic footwear is quite a feat (no pun intended)! I think the pair that I have may be a bit too wide for my feet, unfortunately. They may work with thick socks, but I’m not sure. I didn’t realize they could be machine-washed. That’s pretty amazing! I appreciate your input here.

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