Next up: our coats. But it’s necessary — a recent high of 63F became the next day’s low of 12F. We went back to 67, and are on our way to low 30s.
Winter is coming.
Nay; winter is here.

So, for now, shoes.
If you need a reminder, this is what I’ve said about my shoes in the past.

I am not counting all of my shoes. I have a few in immediate purgatory (set aside to consider for donation/resale), a few in deep purgatory (all but certain I will donate or resell), and many packed away for summer. For fall/winter, here’s what we’re working with:

  1. Everlane Day Heel/black. (Thrifted.)
    I wore these to church yesterday! I find them pretty comfortable. The heel height and stability is perfect. These are a 9.5. They are the right size with the elastic in the back, but would possibly be a touch big (I’m between 9/9.5 after kids, usually a 9.5 in anything heeled, and sometimes an 8.5, most often in sandals). That said, after a few hours, I find the elastic back annoyingly uncomfortable.
  2. Everlane Day Heel/oxblood. (Purchased new.)
    I wear these much less frequently, especially since I’m purging the brown suit I wore them most with and my ONLY dress pants and dresses right now are black/black based. That said, I think they are lovely and they are more interesting to me than a plain black shoe, so I plan to keep them. Part of the issue with these is, of course, that I’m not working outside the home at the moment. I may pack up my better work shoes at some point, rather than donate (much like I pack up my off-season items). These are a size 9. They are snug, especially with the elastic, which becomes borderline painful. I am thinking about cutting it on this pair; I think the 9.5 would be too big if I did cut it on that pair. If the 9s become supremely comfortable, I’d consider getting the black in a 9 and doing the same, then reselling the 9.5s.
  3. Rothy’s Loafer/leopard. (Birthday gift.)
    These are great for church and slightly dressy events, but they aren’t necessarily the GOLDEN SHOE they are marketed to be. I think they are a great gift. I don’t feel compelled to buy more. I love that they require no break in. I like the design and look of them. I think it’s brilliant they are made from recycled water bottles and can be machine washed. I like the shoes. But, they run hot (the synthetic is woven, which helps, but my feet sweat a lot in them in the summer), they have negligible arch support (my arches roll in them to the point of mild discomfort and diminished aesthetics), and they run small (which limits my options/tolerance for swapping in an orthotic bed). They are keepers, but maybe not forever. To my experience they also don’t really stretch, because synthetic.
  4. Talbot’s Suede heel with brass detail/black. (Purchased new.)
    I bought these for Nee’s wedding (our former nanny and, now, dear family friend). I love them. I think they are so beautiful. I tried them on in a 9.5 and they felt blocky/big, so I got the 9. By the end of wearing them for any stretch, I wish they were a 9.5 (because heels). But I’m still very happy with them. I’m so glad block heels came back. I do think I might try to stretch them just a little?
  5. Frye Carson Flat/cognac. (Thrifted.)
    These are a size 9 and also run a little small. I have the same pair in black, which are true to size. I do love the fit and color when I want to wear cognac with black. They have stretched nicely, but you can really see my toe shape in them, which would be less pronounced if they fit more TTS. However, the black flats, which broke in so nicely, feel like they fall off my feet by comparison, to the point that I almost never wear them anymore and am considering reselling them, especially since I have the next pair on this list.
  6. Everlane Day Flat/black. (Purchased new.)
    I bought my first pair of day flats in the bright red 9.5. They felt huge and were too bright for me. So I returned them and stalked the options until a 9/black became available. I wear them frequently! They run TTS for me, though I do still find the elastic uncomfortable by the end of a long day. I think, when they are worn out, I will try something more like the Day glove, which people rave about, and which I follow on Poshmark in different colors, but I don’t need both the Day FLAT and the Day GLOVE at the same time, and like the flats well enough not to want to replace them when they are in good shape and work well for me.
  7. Everlane Modern Loafer/black. (Thrifted.)
    LORD HAVE MERCY WITH THESE SHOES. I love the idea of them so much. This is my FOURTH pair, which probably makes them some of the most expensive shoes I own, even thrifted! I purchased them new in 8.5 before I became pregnant and found them snug, but serviceable, with the promise they’d break in…eventually. By the time I was pregnant a few months later I could NOT GET MY FEET IN THEM. So I sold them. I then bought the same shoe in a 9, because my feet were a little bigger. OUCH. Still not an option, and the 9 felt tiny. SO I bought a TEN, and finally! Comfort! But they were huge. And they were comfortable, but also felt just too big. I knew I’d never wear them. So I resold the 9 and the 10 and sat with this for a bit. I couldn’t stop thinking about them, and a 9.5 popped up on Poshmark, so I bought them and wore them with sock liners for the next half-dozen wearings (they were like new). They are finally pretty comfortable, but I still worry they look big. And I do find my feet (arches) roll in a bit, which is a pet peeve of mine, so I might get some stick-in arches? I have room for an orthotic, but they do feel crowded when I wear one. Anyway, for those keeping track, I bought these new, then thrifted three pairs, and resold three pairs. I would be shocked if I didn’t end up paying $200 for these $155 shoes. Sigh.
  8. Everlane Modern Point Loafer/burgundy and raisin. (Thrifted)
    These are a snug 9.5, due to the pointed toe, which is why I tried the 10 in the Modern Loafer before the 9.5. They are, however, MUCH softer and easier to break in than the Modern Loafer, save for a troubling hot spot (seam) in the inner heel of one shoe, which rubs blisters unless I keep a bandaid on the shoe. They are also splitting a bit at the seam near the toe, but it’s barely noticeable and I may try to fix it. My arches also roll in with these, so I don’t wear them as much as I otherwise would. I think I’ll order stick-in arch pads for both shoes today.
  9. Minnetonka Moccasins/dark brown. (Christmas Gift)
    These have been disappointing, but I love the aesthetics so will wear them until they wear out. My chief complaint is that the stitching near the ball of one foot came apart within a few wears. I was able to pull it closed and knot it sufficiently, and now it stays. But that’s a serious quality control problem. And the leather is weirdly stiff in spots – the shoes have broken in nicely in some places, but remain stiff in others. They are not comfortable shoes for extended wear, so they are largely house shoes at this point, but when it’s hot I usually reach for Birks, and when it’s cold, I prefer my Wicked Good Slippers or even Ugg boots (reviewed below). I do like them in transitional weather with jeans and a tee or sweater once in a while. If I were to get another pair, I’d likely opt for the moose-hide in natural, which looks much softer.
  10. Cole-Haan slip-on loafer/cognac. (Gift)
    These are some of my oldest (and smallest) shoes, but they still work! They are a size 8 and my mom bought them for me in college, back in about 1999. They are timeless. I wear them a few times a year in the spring and fall, mostly.
  11. Frye Dorado Tall Boots/whiskey (Thrifted).
    These were such a find! They are amazing color and retailed for over $450 new. I got them in like-new condition for $139 and I’m thrilled with that find. (Often with popular brands like Everlane or Frye, you’re lucky to find like-new for 10/20% off.) I think I got them just as interest in tall boots began to wane (late 2016), but I have recently enjoyed pairing them with a black midi dress.
  12. Veja V-12/white and emeraude (purchased new).
    These are my newest shoes! I have been eyeing Veja, but concerns about break/in and comfort (and unisex sizing) put me off full-price purchasing. Like other popular brands, I was often finding used shoes for too-close-to-new pricing, or really worn for the asking price. I finally found them new and on pretty good sale (30% off), so I snagged them. I do find the tongue really stiff, but I can also tell these are really well made and will last a long time. I like the ethical/sustainable approach and the 80s retro styling of the V-12.
  13. Nisolo Dari Boot/black (purchased new).
    This was another stalk/buy brand and pair of shoes. I finally had a 20% off coupon and 20% sale at the same time, and I snagged them for about $165 shipped, versus $238. They smelled DIVINE when they arrived and I wear them frequently. I find them very comfortable, despite a higher-than-usual-for-me heel. They have broken in BEAUTIFULLY. I did get the 9.5 and can wiggle my toes, but they don’t feel too big at all. I love these shoes and this brand.
  14. Ugg Boots/tan (Christmas gift)
    I got these back in 2008 and wore them all the time, along with everyone else. I usually wore them at home, though, because they are so…big (especially since they are the tall model and I’m…not tall). I have thought about getting rid of them; they are a (generous) size 8 and I’m now a 9/9.5 in most shoes, but they are still nice when it’s really cold. In “dear lord, please cover my ankles NOW” weather.
  15. Allbirds Runner/charcoal (Christmas gift)
    I asked for these based on reports of comfort and because they are so breathable and washable and stretchy. They have NOT disappointed! I don’t wear them all the time (I don’t wear sneakers terribly often, though I love them), but they are in the “plan to keep until they fall apart” category for me.
  16. Superga Hi-Top/ecru sparkle (Thrifted)
    Um, I love these. I struggle so with the low-tops (they are in my maybe sell pile because I didn’t wear them this summer at all). But these? They work. I think the added support at the ankle keeps them from feeling so noticeably heavy? I also think I struggle a bit with the volume of a 40 in the low-tops (these are a 39.5), because the 39 became too small after babies, but the width of a 37/38 fits my foot better. It does help to wear insoles, but that doesn’t change the weight. Supergas are so classic – I’ve had three pairs since 1992(!) – but I’m not sure they’re for me in the low style.
  17. LL Bean Wicked Good Slipper (Christmas Gift)
    These are so nicely made. I wear them almost every day outside of the hottest part of summer, and wore them SO much postpartum. They are all the coziness of my Ugg boots, but softer and easier to slip on/off.
  18. On Cloud/green pink (purchased new 2015).
    I got these after my twins were born, because I wanted something lightweight, but with a bit of structure (more than my Nike Frees). I really like them. I love the lacing system, which makes them slip ons and which is totally customizable for fit. Four years later, I’m still not running like I’d like, but they are there for me when I do get in a jog.
  19. Adidas Galactic Elite/grey + pink (purchased new 2016).
    I did some workouts with jumping in our (cement sub-floor) basement and realized QUICKLY that the On Clouds are good for jogging, but not good for Plyometrics. Even though I hate jumping, I needed something cushier for when it’s part of a workout – or even part of a warm-up (jumping jacks). These fit the bill. They would also be nice to run in, but I prefer the On Cloud fit for that.
  20. Birkenstock Boston/dark brown suede (purchased new c. 2011?)
    When cloggy Birks had a moment again, long ago, among the middle schoolers, I remembered how much I loved mine and bought a pair. They are a 38, which is shocking, because they fit then and STILL FIT now (I’m usually a 39/40, depending on the style). I usually wear them when it’s socks-n-birks weather, because I’m past the Arizona (sandal) + sock days of late middle-to-early-high school (spring 1992- late 1994). (I loved those days, though.)
  21. Joules Rain Boots/Navy Floral (purchased new 2015)
    I stumbled upon these (probably a return from an online purchase) in my size at Target one day. I had missed my old Target Rain Boots (I put a hole in the top of of one by mistake and had to toss them) and snagged them at 50% off retail. They are a 9 and a touch snug, but perfectly suitable for their use, which has included everything from rainy days to moving 12 cubic feet of mulch.
  22. Classic Bean Boots-6 eye (purchased new 2014)
    I am a sucker for timeless classics. I have always loved these (they feel like the shoe version of an old Jeep Wagoneer), and when they had a style moment a few minutes back, I snagged a pair for myself as an early Christmas present while pregnant with the twins. Part of my motivation was the non-slip sole for winter; indeed, they came in handy both of my pregnancies, as the year I was pregnant with L, we had a lot more ice than usual!
  23. DV Dolce Vita ankle boot/tan (purchased new 2011)
    I got these shoes when folks were just starting to move away from tall boots (and tall boots enjoyed dominance for another 3-5 years, depending on where you live in the US, too). I have always felt they were “not quite right”, but in the dozen or so times I’ve thought about replacing them, I either find something that isn’t better, or is SO much the same, it’s not worth duplicating the expense for the same effect. In the meantime they have gotten REALLY broken in, and now are some of my favorite shoes. I try to remember this anytime a new pair of shoe is a/well made and b/stiff or boxy. They will get better with patience. And these have worn like iron, too – they are actually better today then when I bought them.
  24. 1.State Isak Bootie/gray (purchased new 2017). I bought these through Trunk Club. They are great and have a cut-out, which adds a little flair. However, that also means you can wear them with tights, but it’s hard to wear them with socks, which limits them a bit. Between that and the heel, I do wear them for special occasions more often than everyday (though I did like them for work when I was still in an office).
  25. Sam Edelman Petty Boot/brown (thrifted 2019). I totally was bitten by the influencer bug with these. I can’t say I’m wowed by them. I like the look, but they aren’t super comfortable. I am hopeful that they are like my DV boots in that they weren’t super broken in (they arrived in very good condition), and that, by next year, I’ll think they are the best ever. I do think they pair with skirts a little better than the DV (which skew Western). I did size down 1/2 size for me (I’m usually an 8.5 in sandals, 9 in flats, and 9.5 in very narrow flats, and in heels). My foot is a touch wide at the ball and narrow at the heel/ankle, and I’m a bit flat-footed (worse after pregnancies). I ALSO got this in a lighter brown in a 9 and did NOT like the fit at all, as they felt too long. I also didn’t love the color as much in person with my wardrobe (my browns skew warmer and the 9s are a cooler tan with green undertones), so I’ll resell them.

And that’s it. It’s NOT my entire shoe collection. For record’s sake (and completeness), I’ll review my warm-weather shoes (and the things I’m on the fence about for fall/winter) in the post after coats. I wager there are 15-20 pairs? I will say that, since I started writing this, I did pull my Lotta Clogs out of storage because I want to wear them with socks, but they’ll be reviewed with the summer/sort-ofs, because I didn’t have a photo ready for this post.

Lots of shoes. Just remember, I do share a birthday with Imelda Marcos.

xo, Roo

Leave a Reply