We're Craving a Cozy Fall, and These Are the Shoes (and Outfits!) We'll Be Living In

A comfortable outfit starts at the bottom. No matter the season, feel-good, high-quality shoes will always be in style. In the colder months, add warm to the top of that list — because nothing ruins a day quite like a case of freezing-cold feet! In fall especially, there’s so much adventuring to be had. From casual touch football games to apple picking to corn mazes, there’s no time to be cold or uncomfortable.

Farmer’s Market

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Short ankle boots like these can be worn in so many different ways. Their unique shape gives them a hybrid look, making them work with any outfit you’d pair with sneakers or boots. Play off their sporty vibe by styling them with joggers, an elevated sweatshirt, and polished warm-weather accessories for a trip to your local farmer’s market.

Weekend Getaway

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Elevate your fall style with classic heeled booties. Perfect for a weekend trip, these boots keep style top of mind while embracing your feet like a warm hug. We love how the chunky sole gives them a bit of an edge, with the suede exterior solidifying them as a versatile wardrobe staple. Make them shine in a trend-focused look consisting of a vibrant sweater vest, crisp button-down, and bootcut jeans.

Pumpkin Farm

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Get your classic fall on in fluffy, chestnut-colored boots that are as synonymous with fall as PSLs and vanilla-scented candles. There’s no better place to take them for a spin than a nearby pumpkin patch. And no other boots will keep you as cozy and as warm while you’re there. We especially love how their soft, cushy sock liner makes them ideal in a throw-on-and-go situation. Try styling them with straight-leg jeans and a cheerful cardigan for a fresh, playful look.

Evening Bonfire

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These plush slipper-like boots will level up any fire-pit hangout. Like wearing clouds on your feet, they’re comfortable and practical and oh so soft. We can’t think of better shoes to snuggle up with. Lean into their comfy aesthetic by styling them with equally cozy pieces. We love this relaxed sweat set for its off-duty ease, and this charming plaid coat ties the look together with a burst of print and color.

Foliage Walk

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It doesn’t matter how long you’re on your feet: in these faux-fur calf-height boots, you’ll feel unstoppable all day long. Take them exploring and see what a difference it makes when your feet are toasty and cushioned. Skinny jeans are a no-brainer companion for these shoes, but leggings work just as well. Throw a fisherman’s sweater on top layered under a heavy-duty coat. A beanie in a soft shade provides just the right amount of pop.

Shop These Cozy Boots

  • Advay Boot

    $80

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    Berea Ankle Boot

    $100

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    Delene Mini Boot

    $90

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    Michon Mini Boot

    $90

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  • Victoria Tall Boot

    $110

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