Fall/Winter 2020 Footwear Must-Haves
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.
Need a professional and polished looking shoe but don't want the height? I recently got these flats from woman-owned shoe brand Ally Shoes and am obsessed. Super chic and sleek, this handcrafted leather flat is available in four different widths, padded with an ergonomically-designed insole, built-in metatarsal and arch support, and was designed in partnership with a podiatrist. Wear with your work trousers to the office and your ankle jeans or even your dressier joggers on the weekend. This camel color is a universal neutral that goes with most everything. I've been a fan of Rothy's flats for several years (read my original Rothy's flats review) and love how the shoes reduce waste (they're made from recycled water bottles), are machine washable, hug my foot, and come in some fabulous colors and prints. The Rothy's loafer style is great for winter because the higher vamp offers more coverage and doesn't look odd when worn with socks. While Rothy's offers several solid colors to blend with your wardrobe, I am a fan of their prints, like this Grey Botanicamo pattern which is an unexpected neutral adding fun to an outfit whether it's at home or out and about. Have you been wearing your Birkenstocks all summer and not sure what to do now that it's colder and your toes need coverage? Birkenstock carries shoes and some of them are pretty cute! This Mary Jane style shoe from Birkenstock has the same amazing footbed as the brand's sandals and gets great reviews for fit and comfort. This is the kind of shoe that looks at home with midi skirts and t-shirt dresses as well as straight-leg pants and boyfriend jeans. Keep these at the door along with a utility jacket or puffer and you can go from sleep to street! I love tall boots like these for slipping over leggings, jeggings, and even joggers for comfort, style, and protection against the elements. With a cushioned insole, arch support, a tread sole, and stretch panels along with a zipper for comfort, fit, and ease, this boot will look better with time and wear. Available in three chic and timeless colors. These shoes from Allbirds, made with soft, temperature regulating ZQ Merino wool are a great alternative to slippers as they are more cushioned and supportive. Not only that, Allbirds makes shoes that are carbon neutral, sustainable, and made from ethically sourced materials. While their gray loungers are shown here, Allbirds has a few different styles and many colors to choose from! When comfort and style merge in a season... the clog is back! Yes, this shoe is back in style just in time for fall and winter 'demic comfort. The Dansko Professional Clog is a classic, and looks on trend in this distressed honey-colored leather. I can't think of a shoe that better works with the wide-leg denim styles that are also on trend this season! If this color isn't your jam, the link offers six other colors to choose from. Get the support of a sneaker, the softness of a slipper, and the style of a designer flat with Birdies shoes. 'The Starling' is just one of their styles which come in an amazing array of colors, fabrics, and prints. Crafted with seven layers of cushioning, Birdies provide dual-layer high-density memory foam, shock absorption, and arch & heel support while looking chic. I don't want to freak you out, but the holidays are right around the corner and there's a good . chance your holiday shoes from last year are a style that doesn't fit or work this year. Vionic, one of my favorite brands for comfortable yet stylish shoes, offers this flat with a sophisticated silhouette in amazing colors and prints like this holographic silver snakeskin as well as gold, patent, neutrals in leather, and even a cat-print calfhair. All this style plus an orthotically cushioned footbed that helps support the natural alignment of the foot with every step you take. If you're looking for a stylish flat that has a little more coverage on the foot, this flat from Børn is a great choice. Available in neutrals, on-trend colors, and even a cat print, these flats have plenty of toe room, cushioning and support, and get rave reviews for comfort and style. Not ready to forego heels but want a lower heel and more comfort without sacrificing style? This sleek kitten heel bootie from Clarks offers a padded footbed and support in four colors and prints including this chic black and brown versatile snakeprint and a fab leopard calfhair. With a shaft high enough to slip under your pant hem, these can be worn with your coziest socks and no one will be the wiser. Remember that old commercial with the jingle, "Looks like a pump, feels like a sneaker?" I kept humming that when I saw these slipper/boot/chukkas from UGG. Made of soft suede with a lining from UGGpure, a textile made from wool to feel and wear like genuine shearling, these are just as cozy as a slipper but with a sole and laces to make it a functional, supportive shoe able to leave the home. And don't judge this shoe by this pink color; I chose it because this is a sea of neutrals and I wanted a pop. And the pink IS fun as well as the red, highlighter yellow, and cheetah prints available but there are also neutrals like camel, blush, and black to blend with your existing wardrobe. If you're looking for a boot that will get through whatever the rest of 2020 is going to throw your way, this is a good choice. Since 1870, Blundstonehas crafted comfortable yet durable footwear. Made from sturdy, water-resistant leather, this easy to slip on Chelsea boot has an anatomically designed, shock-absorbing PORON® XRD® footbed for all-day comfort. Available in two colors, these are a great option if you decided to try Doc Martens again and found them uncomfortable but still want that grunge-esque style. They're also perfect for all the wider-leg denim styles that are popular this season.Fall/Winter 2020 Footwear Must-Haves
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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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
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! 🙂
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
I love this list- care to post links to any of them, like the grey boot with rugged sole and the leopard slip ins?
Hi, your dansko link isn’t going to the clogs, just to Walking Co Home page.
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!
I recently got the Ally flats in gray suede and they are fantastic!
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!
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
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.
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.
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?
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!
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.
I just ordered the AllBirds! Exactly what I have been thinking would work for me ~ Thanks!
Can you give advice on socks? I’m really struggling to find socks that are thin, low and stay put!!
Thanks!
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.
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.
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.
Thank you!!
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.
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.
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.