Shopping·12 min read

Comfy and Stylish Shoes to Wear This Fall

Design: theSkimm | Photos: New Balance, Anthropologie, Free People, Nordstrom
September 7, 2023

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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 recommendations possible, we consulted Skimm HQ’rs on the autumn-weather shoes they can’t get enough of.

Enter: Our favorite 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. Traipsing around in the fall leaves = not optional. 

Psst…for more recs to wear to work, when going out, and while at home, check out Fashion You’ll Actually Wear Week, our destination for affordable, stylish, and practical clothes.

New Balance

A pair of New Balance sneakers we can’t believe are still in stock…

Considering how trendy New Balance has been recently, it’s rare to find a pair like these still available. We’re obsessed with the silver and gold colorway and would wear these with a pair of trousers in a heartbeat. You know they’re going to be so comfortable, too. ($154.99, New Balance)

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The perfect marriage between a Mary Jane and a ballet flat…

This fall, it’s all about the ballet flat. Stand out in this ballet flat-style with the added Mary Jane strap for a look that’s all class. Blair Waldorf would wear these with eye-catching tights, so we would too. Plus, they also come in silver. At this price, what’s keeping you from adding to cart? ($59.95, Nordstrom)

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The original Boston Birkenstock with a shearling lining…

When we bought these on a whim, we had no idea how essential they would be to our fall/winter wardrobe. Not only do we wear these supremely comfy clogs on a coffee run, to a Pilates class, or to the grocery store, but also they even look polished with jeans or trousers to the office. ($170, Nordstrom)

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A pointed-toe bootie that comes in the color of the season…

When we spy bright red, we simply have to buy, but these boots are classic in any color. The pointed toe is sophisticated and looks good peeking out of any pants or with skirts and dresses, and the kitten heel is just high enough. ($180, Anthropologie)

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Moto boots that are worth the investment…

We know these are pricey, but we’ve been hearing good things about Reformation’s boots, and we can confirm the quality is worth the price. Between the buckle, the block heel, and the calf-height shaft, these are classic enough to remain a staple in your shoe collection forever. You know they’ll only look cooler (and feel comfier) with time and wear. ($498, Reformation)

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An Adidas sneaker that’s a little less widespread…

Adidas Sambas continue to be incredibly popular, but if you want to stray from the fashion crowd, may we suggest the platform Gazelle? This black and blue colorway will go with everything in your closet. We love the thought of stomping around in these with chunky socks during the colder months, then with our floaty skirts and dresses in summer. ($120, Revolve)

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Frye booties you’ll wear for years to come…

They’re ideal for the fall season, especially since moto boots are back as a trend in a big way. You’ll be able to easily tuck jeans into them or slip them over a pair of leggings. We’ve been wearing these for years, and while they do take some breaking in, they’re extremely comfortable after a couple of wears. ($278, Frye)

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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. Use code skimm923 for $10 off your order of $100. ($135, Allbirds)

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Suede booties to complete the classic fall outfit you’ve been planning…

There’s nothing like a chunky sweater and pair of suede boots to help you embrace the feeling of fall in the air. These have a cushioned footbed and the perfect height stacked heel. Whether you’ve got day or night plans, these boots will be your go-to. ($179.09+, Amazon)

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A pair of sleek sock booties…

With just the right amount of stretch, these ribbed boots are the trendy pair everyone should have in their closet. They make every outfit look more sophisticated, elongating your legs when peeking out of your favorite denim. Each pair is made from recycled plastic bottles, so you can do good for the planet while you look your best. ($150, Everlane)

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Free People

Reebok sneakers if you need a new daily go-to…

If you’re going for a more casual look, Reeboks are perfect to throw on before heading out to brunch, errands, or even the office. They’ve got that vintage flair with a midsole that’ll absorb impact — so when you’re walking around all day, you won’t feel a thing. The low-cut design gives your ankles full freedom and mobility. ($110, Free People)

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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 lightweight foam so you have the ultimate cushioned experience. The mesh is antimicrobial and the heel is molded for a really secure fit. HQ’rs love this shoe. ($139.99, On)

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Sam Edelman

Classic Chelsea boots that’ll truly never go out of style…

These boots have all the details of a classic Chelsea boot — from the back tab to the side goring to the pull-on style — but with an added edginess, thanks to the platform. The contoured footbed helps with the distribution of pressure, so you feel more comfortable as you go about your day. ($170, Sam Edelman)

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Birkenstock shearling clogs that define cozy...

If you need something to keep your feet warm but also make a statement as you run errands or head outside to pick up the mail, these are the shoes for you. They’re the perfect slip-on option that you’ll never get tired of. The cork footbed is sustainably sourced and is naturally insulating. Plus, they’re fully lined in shearling, and the platform will give you a little lift. ($190, Birkenstock)

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Stylish loafers that you’ll actually want to 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. The body is made from Rothy’s signature thread, crafted with plastic water bottles. ($189, Rothy’s)

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Memory foam-cushioned clogs with serious arch support…

This may be an unpopular opinion, but we think clogs are chic. HQ’rs highly recommends these, with more than one person confirming just how comfortable they are. They’re easy to slip into, provide a ton of padding, and have a little buckle accessory we think is adorable. ($139.95, Nordstrom)

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A pair of platform sneakers we’d wear every day for the rest of our lives…

A bold statement, we know, but these Converse are some of the most comfortable shoes we’ve ever put on our feet. They’re surprisingly lightweight, with an angular platform that gives you a little height and a whole lot of attitude. They come in black, white, and pink. ($75, Converse)

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Free People

Platform loafers to take your preppy look to the next level…

Can you tell there’s a trend here? Platforms are in. Besides being downright stylish, these loafers are also comfy. Pair them with jeans, skirts, and dresses. Don’t forget the frilly socks. ($165+, Free People)

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A futuristic sneaker you can wear beyond the gym…

The next sneaker brand having a revival? Asics. These look just as good with a pair of relaxed trousers for the office as they do with leggings for the gym. Plus, if you can run in them, you know they’ll stand up to everyday wear and tear. This red-accented colorway is just cool. ($176+, Farfetch)

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