10 of the Best Fall Boots For Kicking in the Leaves

Everyone knows that those first few crisp days of fall can only mean one thing—boots season! With a seasonal pumpkin spice latte in hand, these staples will have you strutting out of the door, able to navigate life’s busy (or not so busy) schedules. From neighborhood play dates to at-home work meetings and everything in between, put that extra pep in your step with these top picks! They’ll keep you on-trend and comfortable, no matter your mood or style. 

Men were the first to wear heels. In the 10th century, men who rode horses needed their boots to have heels in order to stay in their stirrups.

Sky’s the Limit

Add some length to those legs with these Grayson Tall Boots from Free People. Pair these luxe leather knee-highs with a mini skirt and turtleneck. Perfect for turning a lunch meeting over into a romantic evening—even if it’s just some take out and a rom-com movie on the couch.

Bring It On

Who doesn’t love effortless style? This Sammey Bootie from Dolce Vita will have you feeling those second-cup-of-coffee vibes throughout the day.

Saddle Up

Errand day? Crafted in Portugal, Free People’s Moon And Back slouchy suede boots feature a western-inspired design with a stacked heel for extra comfort. Great to wear with your favorite pair of denim and a simple top.

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Cozy and Confident

Need a boot that makes you feel like you never left the house? Try UGG’s Classic Femme Toggle Wedge Boots. The hidden wedge will keep you feeling cozy and warm even on those rare occasions you have to leave your house.

In the late 1800s, people started calling rubber-soled shoes “sneakers” because they enabled people to walk or “sneak” around without making a sound.

Play Date Approved

This Oshay Pointed Toe Bootie from Marc Fisher is a mom’s best friend. The snake print pattern will dress up any outfit and it’s easy to pull on and take off. Just in case you have to chase your kids at a moment’s notice.

Fringe Up Your Style

Fringe is the accent that will add flair to any style. Add in this bright, bold golden yellow and you’ll be turning heads! These eye-catching, Italian-made Wild Rose Slouch Boots from Free People will take your outfit (and maybe even your day) to the next level.

Mama Fierce

Add some street chicness to your day with Gucci’s Trip Lug Sole Combat Boot. Comfy and stylish for fashion-forward moms on-the-go. Easy to dress up or down paired with a simple sweater dress or to toughen up your favorite fall florals.

Straight to the Point

The sleek silhouette of Free People’s Silent D Cabre Boots will have you seamlessly gliding through your day. These beauties hit just above the ankle which makes them easy to pair with maxi skirts or cropped denim. We love the faux pink alligator and buttery, honey-colored boots for fall.

Dr. Martens were originally considered practical working men’s boots for their air-cushioned soles.

Built for Anything

These are the quintessential fall boot! Tried and true, the Henderson Weatherproof Chelsea Boots from Vince are a go-to for anything your day may throw at you. A lugged sole and chunky block heel bring a utilitarian attitude to this outfit-making staple.

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Never a Dull Moment

An oldie but a goodie, these timeless Dr. Martens Jadon Lace-Ups stay true to the classic “eight-eye boot” style but bring a bold platform and bright accent to your fall wardrobe line-up.

Platform shoes used to be worn by Greek actors to signify status. Tragic actors would wear “buskins,” or raised platform shoes, to symbolize their superiority over comic actors, who would wear plain socks.