State of the Wardrobe: Shoes

A long post about my shoes. How much I’ve been wearing them and why, how much I’ve spent on them, cost-per-wear and wears-per-month, and a look back on my shoes of yesteryear.

Current shoes

It’s been a while since I actually did some good old fashioned Airtable stuff, and given how by far the most popular pages on the site are the wardrobe tracking ones, I thought it would be good to dive back in for a post as well as have a look back on how my shoe collection has changed.

If you’re interested in tracking your outfits or just inventorying things, check out Wardrobe Inventory and Outfit Logging Methods for a list of pros and cons of different approaches including Airtable, spreadsheets, and proprietary apps like Stylebook.

Here’s a gallery view of all my current 24 pairs of shoes sorted in descending order of wears per month as well as total wear count since January 2018 (when I started this Airtable database) and cost per wear:

(click the image to view it full res in a new tab)

shoes gallery cpw and wears per month nov 2019

The black sneakers and sport sandals high wear counts because I often wear them to volunteering, but I don’t really think of them as “outfit” shoes anymore. The flip flops are “going around the building to the laundry room” shoes which don’t get recorded.

And for a view where you can more easily compare the actual data, a sheet view (click image to open full size in new tab):

shoes statistics november 2019

The sheet I realized afterwards didn’t include the few “gear” items like rain boots, but I didn’t feel like redoing it.

An Aside

So, Airtable does have a spreadsheet view, and in terms of sorting, filtering, and grouping things as well as having a gallery view option, the UI is much nicer, but the browser extension I usually use to take full page screenshots apparently needed permissions to “read and change all your data on the websites you visit” in order to auto-scroll a page with an iframe in it (apparently the sheets view uses iframes, but the gallery view doesn’t?). I mean, it could be legit. But also how about no.


So instead I exported the view as a CSV file, pasted that into google sheets, converted the Photo field into embedded images, realized that the extension doesn’t know how to scroll within a google sheet, exported the google sheet as an HTML page, loaded the HTML page in the browser, then took a full length screenshot of that because I didn’t feel like making a nice chart with thumbnails totally from scratch.

On the other hand, it looks like google sheets has a much less jank way of embedding images into cells now, which is nice.

If you decide to sign up for Airtable, you can use my referral link which will give me a few dollars in Airtable credits at no cost to you. Otherwise, you can sign up at I am not partnered with Airtable and otherwise do not receive any money for plugging it. I’m just sharing because I have personally found it a very useful service.

The free tier of the app should be plenty for personal use as a wardrobe tracker. However I additionally use it for other projects.

Instead of looking at just wear count, I prefer to look at wears per month (WPM) because it’s easier to grok.

For example, if someone tells you they wore a pair of shoes 25 times last year, it’s harder to intuit what that really means, but if they say they wear it about twice a month, that’s a more familiar way of thinking of clothes for most people.

Wears per week can work too, especially if you have a more minimal set of shoes, but I find that there are always a few pairs that don’t get worn very much either because they are formal, weather specific, or hard to style, and the number for WPW (for example, with 5 total wears is about 0.1) is harder to visualize than WPM (for 5 total wears is about 0.4, or about once every other month).

WPM is also nice because you can get a sense of how much you’re wearing something compared to other things right away. With just wear counts, you have to wait a few months or even years before the counts start becoming comparable.

Most-worn shoes

  • There are 21 outfit shoes (not include hiking boots, rain boots)
  • 10 have WPM > 1
  • 7 have WPM > 4

top wears per month shoes november 2019.png

Aaaand yep, those would be very reasonable choices for a minimal shoe capsule, should I ever need to pare down.

  • Black boots are clearly a staple for me, but within the three pairs that made it here, the chunky, low-set silhouette of the 1460s are unique within this set, and the patent leather lace-up boots are a lot louder from the shine and texture of the eyelets than the chelsea style boots)
  • A good spread of weather is supported, and there are casual and dressier options for warm and cold weather
  • They all fit into my current preferred style of a vintage inspired, feminine but not fussy look
  • While there aren’t really any “WOW” statement shoes, these are all pretty easy for me to style with the clothes (particularly bottoms – gotta get that shoe-pant-interaction right) I have. There are things that work for wide leg pants, tapered loose pants, straight leg and skinny jeans, and skirts of different volumes.

It’s interesting that even though I now have nicer shoes, I still pretty much rotate between open shoes, boots, and sneakers like I did before deciding to actively focus on clothes. Ballet flats, mules, and loafers and I still have a hard time getting along, but since the collection is so well rounded, I am totally okay with not working to branch out for now.

Least-worn shoes

Here in the bottom third of WPM, we unsurprisingly find all the statement shoes and formal shoes.

least wears per month shoes november 2019.png

Besides things that are simply formal (pumps, suede sandals), I’m less likely to wear something if it’s

  • uncomfortable – The tan lace-up boots seem like they’d fit in with the more worn items, but they require wearing socks that are taller than the shaft, which has an unfinished, chafe-y edge that I did not realize was that way until I had walked half a mile in them. But aside from those, everything else is actually pretty okay
  • only go with one or two bottoms (cut or color)
    • Tall boots only work with leggings/tights and skirts, and with anything but leggings and a sweater they end up feeling too extra for the office.
    • The Hieronymus Bosch docs, while being the coolest docs ever to be produced, have a busy print and a chunky silhouette, so I realized that I really only like them with tights, leggings, or bare legs so that the shoe-pant-interface is just not something that needs to be worried about at all. The things are just so loud on their own they need some breathing space, at least with the types of clothing I have.
    • Tbh I just haven’t figured out the metallic oxfords yet. I have a pretty hard time with color coordination, and the purplish metallic is annoying

I’ve been quite careful to not buy anything that is uncomfortable for me due to heel height. But I don’t wear my statement shoes as much even if they are flat. Hoping to change that this coming year since I recently found a combo I like for the tall boots (leggings and a flowy. sweater, or a short smock dress), and a combo for the printed docs, which I realized I like best with tights or bare legs because otherwise they feel like they’re competing/clashing with the bottoms.

Another thing of note is that I really needed the right “wardrobe infrastructure” to support statement shoes. Current set of shoes would not have worked in my 2017 wardrobe which was mostly black and gray stretch fabrics.


I’ve spent $2,522.30 on just the shoes in the spreadsheet, which even now amazes me. I grew up mostly with Payless and Target shoes being told “It’s the same styles! Look how much you’re saving! Hah, all those people paying hundreds for shoes are suckers” but in my experience, that shoes with actual leather in the $100-$200 range have typically been a lot more comfortable, better-looking, and wear out more gracefully. Cue the ol’ link to the Vimes quote on boots. (Of course in terms of value, none of this matters if you end up not wearing your very nice boots anyway. I espouse the strategy of getting a cheaper pair of shoes (that’s still comfortable enough that you’ll actually wear them) if you’re still figuring out if you’ll actually like a style.)

Financial context

I’ve been working as a software engineer at startups in San Francisco since 2016 and my salary starting as a new grad was $95k. It has since increased significantly, mostly through pay bumps from switching jobs. I don’t have a car, kids, pets, or (fortunately) debt. Fashion is my only hobby that results in high spending. So while $2.5k on shoes in two years is a LOT, I’m very privileged in that about $100/month going to shoes on average wasn’t a financial burden. It’s definitely something I want to slow down though. Can’t buy shoes faster than I actually wear them.

Thoughts on tracking cost-per-wear

CPW is under $5.00 for more than half the shoes, which I’m pretty happy with given how most of them were over $100 to start with and that all the ones with low wear rates are either statement shoes or formal shoes.

I don’t really like optimizing for CPW as a primary goal when it comes to building a wardrobe. For me, since it’s the dressing up part that’s fun and I adopted this whole wardrobe curation endeavor largely as a hobby and not as a purely functional venture, while I do want to make sure all my items get regular wear, I think it’s more helpful to shoot for a higher number of wears in outfits that I actively like. Optimizing for awesome rather than budget, while keeping budget in mind. I’ve definitely had shoes before (particularly black ankle boots) that I’ve worn out and had <$1.00 CPW, but I wasn’t actively happy with most of the outfits I had with them. They were just functional.

I tag my outfits on Airtable as liked/loved/favorite, and for the past few months almost all of them have been at least “liked” (this in itself is a whole other blog post). Looking at the Favorites field, the shoes that get worn often and in favorite outfits are the t-strap clogs, Birkenstocks, and patent leather lace-up boots. I think I need to convert this to a rate of (count of outfits it’s in that are favorites / total count of outfits it’s in) because I think the Birkenstocks just have way more wears than anything else to start with, and I have fewer summer shoes than boots so the clogs get a boost from that.


Some of the priciest shoes here are the Bosch 1460s, which you can read more about here. These are inflated eBay prices because they were a limited edition run from the museum collection a few years ago.


The cheapest shoes are all secondhand Born shoes from eBay and Poshmark. I find that I still really like the oxford styles that had a moment around 2010 when twee was popular, but there hasn’t been much choice in stores recently (it’s all loafers), so I went for online.

Shoevolution, a retrospective

Most of my shoes were purchased within the past two years. I did a wardrobe overhaul in 2016-2017, and before that I had a still not terribly minimal collection of 19 shoes (rain boots, flip flops, and athletic sneakers not pictured) vs 25 today, which kind of surprised me because I didn’t really consider myself a Shoe Person back then.

I didn’t have stats from these (I took this inventory right at the beginning of when I decided to overhaul), but I mostly had the gray boots, sport sandals, and sneakers on rotation. IIRC I actually never wore the heeled sandals during the time I owned them, and only wore the flats, espadrilles, and sandals a few times each. Mostly because I didn’t find them comfortable, but also because they always felt tacked on to my outfits, which mostly consisted of the free t-shirt, jeans, and hoodie combo.

shoes 2017.jpg

I don’t actually think this is a bad collection at all. It covers all the practical bases and I think fondly back on all the fun well-worn sneakers. It is pretty youthful vibe overall though – I could easily picture any of the sneakers, sandals, and flat boots on the parade of kid visitors to the museum I volunteer at on the weekends. Not that it’s a bad thing, but at the time (just post-grad) I decided that it didn’t really feel like who I was anymore, and I wanted to go for a more refined/edgy style. (For more on what elements make things read as youthful, see my post on How to Look Older in Casual Clothes)

Fast-forward from that snapshot of 2016 to 2017:

A lot more black, more medium height block heels, and a few more pointed toes.

I mostly rotated through black ankle boots, with the occasional appearance by the tan boots or black flats. For warm weather, I was still mostly wearing the sport sandals. I’d branched out to the leather block heeled sandals, but I remember thinking that those still didn’t feel right for what I was going for (turns out that clogs were what I was looking for) even though they did feel more polished.

The wear counts here are for these items through the end of 2018, because I couldn’t be bothered to configure it to just show the 2017 ones, but the distribution was pretty consistent.

shoes 2017.png

For the low-wear count shoes,

  • the brown boots did get a fair amount of wear up through 2016, but I think I was really on a everything must be BLACK and MINIMAL and CHIC and EDGY kick and eschewed and eventually donated them. Funnily enough, I have similar boots again now, although they are at least nicer versions (these were no-brand faux leather ones with heels that disintegrated when rubbed into the floor that I’d bought at Savers many years ago).
  • The oxfords I actually liked the color and style of, but they were cheap polyurethane ones from Amazon and were horrifically uncomfortable (they did help me decide that I wanted to shell out for a better pair, cue the entry of the Born oxford pumps from eBay).
  • The sneakers were the aforementioned exercise sneakers that didn’t get incorporated into Outfits often, although looking back I’m pretty sure those are meant to be street sneakers and not workout sneakers.
  • I remember at the time thinking the high heeled booties were like, the platonic ideal for the style of boots I wanted, but I think they just didn’t jive with my foot shape because I was never able to get comfortable enough in them walking around a bit at home to wear them out, and the one time I did for a party was pretty terrible.

It’s interesting to see the progression in trends when looking at the shoes as well. Sneakers got chunkier, boot shafts got higher and more fitted. I think this generally follows macro trends in recent years, which go along with the change in pant silhouette from skintight full length pants to looser, more cropped pants which look better with a taller, sleeker boot or a shoe with more visual weight. Most of the time when people show old outfits from 10 years ago and go “hah hah look how bad this looks” I feel like at least 70% of the “bad” is just “not on trend anymore” and the other 30% is because it’s a high school picture and were still figuring clothes out.

While this was an improvement over the original set in terms of being closer to my style goal at the time, I felt like I did not have the variety of shoes for the variety of outfits I wanted to make. Too many booties in the same shape, no summer footwear or sneakers I actually liked.

Concluding Thoughts

  • Once I get that corduroy skirt hemmed I should aim to wear one of the statement shoes once a week while the weather is suitable for them until they become as intuitive to wear regularly as the others shoes.
  • Someday I would like to get my hair and makeup game up to the point where I can wear chunky sneakers with almost anything and it will read overall as practical but still fashun (I got the New Balances because u/full_boyle on reddit wore some in her now-deleted Japan travel post and she looked so good but I have come to the conclusion that it was mostly because she is on an entirely different plane than I am when it comes to hair and clothes)
  • Shoe-related things I’m considering getting that seem sensible
    • Some kind of chunky black sandal for summer, since I’ve had multiple outfits this year where I felt that the Birks weren’t visually heavy enough but the tan clogs didn’t quite work. I need a second walking sandal that works as an “outfit” shoe anyway for vacations to avoid a repeat of the smell-tastic outcome during my DC trip.
    • A replacement for my pleather leggings that wore out. They would also go with the docs and tall boots.
  • Shoes that I should not get
    • Any more formal shoes (3 is plenty!)
    • Shoes that don’t go with any of my jeans (everything in the high WPM group goes with at least either my light blue jeans or washed black jeans)
    • Any more docs, since the ones I have will probably never wear out at the rate I use them (on the other hand, my boyfriend bought his around the same time as me and his look like they’re on track to wear out some day since he is not at a desk 100% of the time)
  • If I continue the trend of increasing the average visual interest of my wardrobe, for shoes, if I get “extra basics” like the platform clogs or patent leather boots, those will probably get a lot more use than something that is a “statement” as in “doesn’t go with a lot of my core pieces”
  • I need to pay more attention to whether I have bottoms/outfits that work with shoes in office appropriate outfits when buying things. A lot of things I like with tights and short dresses/skirts/shorts and that’s what I picture in multiple outfits when I’m buying them, but that isn’t actually a look I wear often. I also find it harder to style less feminine shoes to my liking (i.e. full on combat boots like docs vs the softer brown granny boots), so I should err towards more feminine styles in the future
  • Tracking wears and keeping outfit photos has been good for picking out patterns and keeping it real and forcing me to think about how I can use all of my wardrobe

What about you? Accounting for formality and weather, do you mostly rotate through your shoes evenly or are there some shoes that you find are a lot easier to style in your wardrobe? What would need to change to reduce the friction in styling the less worn ones?

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