Fall/Winter 2020 Footwear Must-Haves

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It's a new year, a new way of living, and with it we all have new needs for our fall and winter footwear. Maybe we're telecommuting after years of heading to the office, maybe we've decided to give up the high heels, and possibly we've found over these months that our personal style has changed and with it our previous footwear wardrobe no longer works for us. I know my needs have changed and I have been looking for styles that offer support, comfort, and durability while also remaining stylish and working with my personal style. Since I was searching myself, I figured you may be looking as well so I gathered some styles that offer what we may need this year versus last year. Below, some of the must-haves for many footwear wardrobes for this fall and winter.

Fall/Winter 2020 Footwear Must-Haves

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I'd also love to hear from you! What shoes are you finding are getting a lot of wear now that the temps are dropping? Are you finding that your fall/winter 2020 shoe wardrobe is different from what you wore this time last year?

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  1. I inexplicably want some aggressively ugly nylon puffer shoes or boots. Like the kind that look like you have strapped sleeping bags to your feet. I don’t know if it’s a passing moment of madness or an actual style moment, it just seems like the thing I need right now – something slip on, water proof(ish), and cozy for outdoor visiting and morning walks. Preferably in some kind of loud color or metallic finish. Really, no idea what’s come over me. Lol

  2. I am cracking up that my always is the new normal. My Blundstones, Chacos, Born, Danskos, all Birds, even my Stegmann or Haflinger boiled wool, tread- soled slippers….
    Mountain town kindergarten teacher style for the win! 🙂

  3. This fall my shoe lineup is as follows
    -black vans ward low sneakers
    -a slip on gray ankle boot with a rugged sole
    -red danskos
    -leopard slip ins
    -backless low heeled slip on mules in leather from. Free people

    1. I love this list- care to post links to any of them, like the grey boot with rugged sole and the leopard slip ins?

  4. I love shoes so much; they are seriously my favorite thing to buy! Since I work in public education, I tend to dress casually and am mostly indoors, plus I live in the South, so there’s not a huge need for “serious” winter shoes. However, I did finally buy myself two pairs of ankle boots that look like normal boots but are waterproof. One is from Sorel and the other is from Uggs (not the old-school Uggs). Both look great with jeans and pants, which is mostly all I wear; they are comfortable; and it’s so nice to not worry about wet feet when the weather is yucky. They are a great casual option. My other favorite shoes are loafers from Sperry. Honestly, they are one of the few pairs of shoes I’ve ever gotten that felt wonderful from the first time I wore them. SO comfortable; the leather really did seem to mold to my foot. Started with a cognac pair and picked up a grey pair too. Love both. The one shoe I want but haven’t gotten is a pair of Rothy’s. Every time I think I’m ready to bite the bullet and treat myself, something happens. So maybe, just maybe, I’m going to tell my husbands I want a pair for Christmas!

  5. Allie- thank you so much for this post! With the rain arriving to Portland Oregon, I have been thinking about putting the Birks and Chacos away. Sadly, I’m not feeling the Stan Smiths I impulse bought at the Adidas Employee store last spring either. Too summery, white shoe.

    I was wishing for a post just like this and hoped you would put one out! I was thinking about the Danskos in that exact color you posted. But also thinking maybe a high top sneaker might be better? I’d love to see a high top post although I know they aren’t your personal style (as far as I can tell). I also need a new pair of rain boots as my bog booties from the past 3 years have a hole. I don’t want to spend a ton on shoes this year. I’ll buy two pairs tops. Thanks for this!

  6. What I’ve actually been wearing this fall:
    * Birkenstocks in the house and almost everywhere else on warm days
    * running shoes for walking and running
    * Chucks or Sperrys for getting “dressed up” for the grocery store, doctor/dentist appts (with Smartwool Hide & Seek or Secret Sleuth socks)
    * Driving mocs (Ugg and Blondo) for patio dining
    * Hiking boots for hiking (La Sportiva, bought at REI a few years back: 1/2 size smaller than my running Nikes, 1/2 size larger than most of my casual shoes; daughter really likes her Ariat hikers and they are both more attractive AND waterproof)

    Now that it is getting colder or wetter, I will be pulling out the waterproof boots and booties. Just put away most of my sandals and pulled out booties this weekend.
    * LL Bean wool slippers–new pair is not a comfy as my old ones, hope they break in soon (not waterproof, but can go outside to get the paper)
    * Blondo booties for “dressy” events (note that Blondo also makes some water-resistant loafers / mocs)
    * La Canadienne riding-style boots for “dressy” events
    * J Crew chelsea style rain boots
    * Hunter rain boots
    * Bearpaw (Ugg-style boots that are actually water-resistant) for block happy hours
    * Sorel Joan of Arctics for winter dog walks
    * Smartwool socks with almost everything

    1. Thank you for sharing this list! I have similar taste but not quite enough storage for all these shoes. I will check out Blondo as I’m in Portland, OR and it’s constantly wet/dry here.

  7. Waterproof but comfortable—shoes that will be good for walking in the winter, so that I don’t have an excuse not to go out. I’m concerned that come winter, i will not leave my house, and so I’m gathering shoes that will allow me get out daily and walk.

  8. These we great. I am deeply devoted to Dansko (when things reopen, for folks in the NoVa/DC/Maryland area, there’s an outlet in Southern PA that near some great Amish and Mennonite farms; I take my kid and have an excuse for ice cream at Maplehofe Dairy or drive further to Lapp’s or hike along the Susquehanna).

    I also like clogs. Maguba, Troentorp, Lotta, Has-been, etc. They can be $$$ but you can find them gently used and on sale. I wear them with fun socks and their bright colors cheer me up.

    Alison, can you recommend some serious boots? Walking every day is helping my mood, as is weekend hikes. I’ve been wearing sneakers but as the weather gets colder/wetter, they won’t work. Looking for waterproof, good tread, ideally less $$$ than Danner. Any favorite brands that hold up well?

    1. Not Allie, but I have feet problems and needed really comfy hiking boots. I got the Hoka hiking boots. Expensive but we hike a ton and backpack, and they are great for long walks in the city as well.

      I love your clog ideas, so thanks for listing those! I had been eyeing the Danskos in the very same color that Allie posted here! Guess that means it’s meant to be. I had been wanting to look at boots, but didn’t have the energy to go through all the options by myself. Thank you and Allie and others here for posting these ideas as a great starting place!

  9. I bought a pair of leopard print suede booties with a zipper on the heel. Love that detail. Livvy Bootie by Journee Collection. I’ve walked a couple miles inside my building trying them out. I’ve now waterproofed them for winter wear.

    Sadly I’ve had to retire my Aerosole leopard flats. Too flat for my feet after developing bone spurs so I’ve been looking for something in leopard print I can waterproof (calf hair can’t be waterproofed). Between bone spurs and bunions, I’ve had to donate several pairs of shoes.

    Think my shoe shopping is done for the season.

    1. I really like these short boot socks from Smartwool. They aren’t chunky but because they’re merino they give warmth and they fit my size 8 feet pretty perfectly: https://shopstyle.it/l/bngJR

      I also got these as athletic socks also from Smartwool but I am loving them for all sorts of situations. They don’t restrict my ankles but have a really great fit that they don’t slide down even inside my slipper boots: https://shopstyle.it/l/bngKK

      Smartwool continues to be my favorite for any kind of sock. Good fit, hold up well, their no-see styles truly disappear under shoes, and warm without being bulky.

      1. Similar to Smartwool, I like Darn Tough Vermont. They have such an easy try and return policy (free both ways) and a lifetime guarantee. For anyone who’s a veteran or first responder, they also offer a great discount. I found the wool a little softer than Smartwool, and I like the colors and styles at DTV.

        1. I am a Vermont native and LOVE Darn Tough! So much stronger and just as comfy as Smartwool. AND made in USA with a lifetime return policy.

    2. I just purchased men’s no-show socks from Uniqlo and I think they are the best – even after shrinking a bit in the dryer, that stay in place and they’re comfortable.

  10. Like Ann Marie, I haven’t worn shoes in months. My closet full of gorgeous heels and loafers in the much-coveted size 10.5 — my hard-won collection! — sits unused. I try not to even think about it, but I do wonder if I’ll end up just giving away or selling all of them at some future point. I definitely won’t be buying shoes this season and anticipate wearing nothing but Glerups or Haflinger slippers pretty much nonstop this winter. The occasional trip out requires nothing more than some slip-on sneakers. Sad.

  11. Until recently, I had not worn anything other than some kind of sneaker since March. This month I wore my chunky loafers twice but as it gets colder, I will probably not wear them. Given that there will be no where to go, other than for a walk, once it gets colder and darker, I don’t see myself wearing anything but sneakers or maybe occasionally a Chelsea boot.

    I had wanted the Blundstone boots but didn’t want to pay the price so I bought the Eastland Ida boot in dark brown from Macy’s when they were on sale. It looks similar but is a lot less expensive.

    Overall I will not be buying anymore shoes this year. I also probably won’t buy anymore more clothes. I plan to “use up” what I already own and when I do eventually go back to working in an office (likely next spring at the earliest), I can then buy new shoes (and clothes) without any guilt.

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