How to Style Ankle Boots for Fall

If you’re anything like us, the best ankle boots likely get the most mileage in your day-to-day wardrobe. And it’s no wonder—flat or heeled, they’re endlessly incredibly comfortable, versatile to style, and ready for any weather scenario that comes your way. They’re a smart investment if you’re in need of a new pair—not to mention one of fall’s top boot trends, imagined in both trending hues (burgundy! chocolate brown!) as well as print (leopard! snake skin!) and material (calf-hair! suede!).

Speaking of suede, the material is seemingly everywhere, and it’s reached ankle boots, too—from dark brown to warm cognac, this luxe texture looks great with other fall standbys like leather and denim. We’ve also been loving the embossed croc look, which elevates standard black leather boots to something a little more dressed up. Of course, you can never go wrong with the classics. Timeless Chelsea boots are always city-chic, and punky platforms like The Row’s signature zip-front boot are ready to stomp come rain, snow, or shine.

Whether you’re looking to shake it up this fall with a statement style, or just looking to invest in a new signature, these are the best ankle boots to shop for the season ahead—and seven ways to style them from the ankle up.

Downtown Cool

Khaite’s Nevada boot is a signature for a reason: the subtle western detailing and sculptural heel are effortlessly cool, ready to dress up or down as needed. With your favorite pair of jeans and a laidback leather jacket, these boots are ready to pound the pavement.

Leather and Lace

Mix and match textures by pairing croc-embossed ankle boots with a lace-trimmed skirt and a lush, oversized knit.

Countryside Core

Gucci’s boot-meets-loafer hybrid in deep brown suede is built for crisp fall strolls. Wear it with winter whites, a plaid barn jacket, and just a peek of preppy sock.

Stomper Meets Slipdress

Astudy in contrast, The Row’s chunky zip-front ankle boot plays well with a daintier satin dress. A suede tote and simple pendant are elegant touches that keep the look from tilting too far into grunge territory.

Office Polish

Keep work attire grounded with a high-shine Chelsea boot. Alongside your favorite trouser and button-down, topped off with a cropped suede jacket for a winning, casual-cool combo.

Ladylike Refinement

Toughen up a staid pencil skirt by opting for one in luxe leather. Cashmere adds sumptuous texture, while heeled ankle booties give the look a sophisticated finish. Opt for jewelry extras in a similar silver tone to match the embellishment on Tory Burch’s pierced bootie.

Model Off-Duty

Ground mini shorts and a scarf top with lace-up ankle booties. Oversized shades bring the requisite drama of an early aughts supermodel arriving late to her fashion week fitting.

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