13 Comfy and Stylish Shoes to Wear This Fall

Published on: Sep 16, 2021fb-roundtwitter-roundemail-round
comfy and stylish shoes for the fall seasonDesign: theSkimm | Photo: On, Birkenstock, Sam Edelman

We don’t know about you, but as soon as there’s a light breeze in the air, we’re just itching to transition from flip-flops and sandals to booties, loafers, and clogs. To give you the best recs possible, we consulted Skimm HQ’rs on the autumn-weather shoes they can’t get enough of. 

Enter: Our fave options that rank high in the comfort and style departments. We’re talking about pairs you’ll want to walk more than a few blocks in. And many that’ll perfectly complete your IG-ready, the-leaves-are-changing-and-I’m-outside outfit.


allbirds womens running sneakersAllbirds
Allbirds running shoes made from renewable materials…

Thoroughly tested by both pro and amateur runners, these sneakers have serious support and cushioning ideal for road running. The midsole is made from sugarcane, while the body of the sneaker is made from eucalyptus trees. We’ve been running in them for weeks and find them to be extremely lightweight, breathable, and comfortable. ($125, Allbirds)

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frye black short bootiesFrye
Frye booties with hand-knit soles that are durable and waterproof…

They’re ideal for the fall season, especially since they’re short. You’ll be able to easily tuck jeans into them or slip ’em over a pair of leggings. Reviewers say they take some work to break in the leather, but are fully worth it once you get that worn-in feel. ($278, Frye)

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black buckle biker bootsNordstrom Rack
And a pair of buckle biker booties to up your streetwear game…

Also waterproof, this pair is great for everyday wear when you need to put an outfit together quickly. They go with basically everything and can immediately enhance your style factor without much effort. One Skimm HQ’r owns a pair and says they’re comfy enough to wear on long days spent outside when you’re doing a ton of walking. ($64.47, Nordstrom Rack)

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sorel chelsea rain bootsAmazon
Sorel Chelsea-style rain boots for blah weather days…

No need for cumbersome rain boots when these marry style with function. One Skimm HQ’r raves about them, highlighting their comfortable footbeds that mold to your feet. She’s worn them on both long hikes and to sit-down dinners, proving they’re a versatile shoe that’ll come in handy on more than one occasion. ($65+, Amazon)

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blue suede bootsAmazon
Suede boots to complete the classic fall outfit you’ve been planning…

Nothing like a chunky sweater, flat-brim hat, and pair of suede shoes to help you embrace the feeling of fall in the air. So whether you’ve got day or night plans, these boots will be your go-to. ($129.88+, Amazon)

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everlane black sock bootsEverlane
Everlane glove boots for a sleek and sophisticated look…

With just the right amount of stretch, these ribbed boots are the trendy pair everyone should have in their closet. Each pair is made from nine plastic bottles, so you can do good for the planet while you look your best. ($120, Everlane)

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reebok sneakersAmazon
Reebok sneakers if you need a new seasonal go-to…

If you’re going for a more casual look, Reeboks are perfect to throw on before heading out to brunch. They’ve got that vintage flair with a midsole that’ll absorb impact — so when you’re walking around a city all day, you won’t feel a thing. The low-cut design gives your ankles full freedom and mobility. ($40+, Amazon)

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puma sneakersAmazon
And a pair of Pumas that are iconic for a reason…

They’ve got a rubber outsole that’ll provide traction and grip, so you won’t feel like you’re sliding when on slick surfaces. You’ll get the classic formstripe but with an updated and modernized design that’ll equal all-day comfort. ($39.95+, Amazon)

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running sneakersOn
Sneakers with a speed-lacing system so you can slip them on and off…

If you’ve ever wanted to walk on a cloud, here’s your opportunity to get close. These shoes are made of Zero-Gravity foam and CloudTec so you have the ultimate cushioned experience. The mesh is antimicrobial and the heel is molded for a really secure fit. What can we say? Skimm HQ loves this shoe. ($129.99, On)

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sam edelman black bootsAmazon
Sam Edelman Chelsea boots that’ll truly never go out of style…

These boots are made with extreme attention to detail, meaning the curve of the shoe allows your foot to be evenly placed. This helps with distribution of pressure. So you feel more comfortable as you go about your day. ($169.95+, Amazon)

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shearling birkenstock clogsBirkenstock
Birkenstock shearling clogs that literally scream ‘cozy’...

If you need something to keep your feet warm as you run errands or head outside to pick up the mail, these clogs are a must-have. They’re the perfect slip-on option that you’ll never get tired of. The cork footbed is sustainably sourced and is naturally insulating. Goodbye, chilly toes. ($190, Birkenstock)

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loafersRothy's
Stylish loafers that you’ll actually wanna commute in…

What’s ideal about these is that they’re both structured and flexible. So they’ll feel substantial on your foot as you head from your apartment to the subway to the office. The raised nubs on the bottom provide that extra bit of grip too. The body is made from Rothy’s signature thread, crafted with plastic water bottles. Psst...remember that these aren’t meant to stretch much, so if you’re in between sizes, go up. ($185, Rothy’s)

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clogsNordstrom
Memory-foam-cushioned clogs with serious arch support…

For some reason clogs get a bad style rap, but we’re here to banish that idea. Skimm HQ highly recs these, with more than one person confirming just how comfortable they are. They’re easy to slip into, provide more than enough padding, and have a lil’ buckle accessory we think is adorable. Case closed. ($134.95, Nordstrom)

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If you buy anything from this email, theSkimm may get something in return. Oh, and if something’s out of stock, oops, it was there (and all prices were accurate too) when we published. Thanks.

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Skimm'd by Alexandra Napoli & Emmy Favilla