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The Big Short: The 9 Best Ankle Boots and How to Wear Them

Not quite ready to pull your heavy-lifter boots out of the closet? Our fashion pro, Kimberly Cihlar, says shake some booties this fall with these 9 ideas for easing into cooler weather.

We’re in that in-between stage of the season. It’s getting ch-ch-chilly but not full-on freezing. This is when booties, the younger cousin of the knee-high variety, make the most sense–with pants, of course, but also with leggings, skirts, and dresses. Yep, fall ankle boots are a perfect segue into cold weather.

Here, we look at the long history of short boots, how best to wear them, and the coolest styles now.

The Roots of Short Boots

Short boots hearken all the way back to the 1800s, when women and men stepped out of knee-high riding boots. In the 1960s, came the hybrid “shootie,” as some called it, crafted with elasticized rubber at the ankle for easy on-and-off. Voilà, the Chelsea boot was born. The abbreviated boot had a moment again in the grunge years of the ‘90s, when post-apocalyptic Dr. Martens and other engineer boots were juxtaposed with baby doll tunics and slip dresses.

Now, as the pre-frosty days of fall appear, booties are the obvious choice for ramping up your style game without having to go with the full-monty style, a look better suited to shivering temps.

Read More: Hats Off to Winter: 7 Ways to Keep Warm, Look Cool

How to Wear Fall Ankle Boots

*Rock the ankle bootie with a bare leg if you’re game to show your gams. Short dresses and skirts, both A-line and figure-forming, look great with an ankle bootie. Long, flowy maxi dresses pair well, too, giving a flash of spunk under the fabric. Skirts with a high slit allow for maximum leggage.

*If the weather is cool enough and you don’t want to expose so much of your own skin, wear tights with your booties. For a long line, consider coordinating the color of your tights and bootie. This season, the hot hue is aubergine (aka eggplant, oxblood, or merlot). This creates a long line for the eye, elongating the leg in the eyes of the viewer.

*Wearing booties with leggings is an easy style get. They also work well with a sleek, peg-legged pants look and flared jeans.

*Go bold with booties in neutrals of silver, gold, and leopard (NextTribe’s style fave) that can go with any and every kind and color of short dress. Our own editor-in-chief, Jeannie Ralston, swears by her silver peep-toe booties for both casual and dressy events.

*One styling caveat: Wear sleeker booties under long dresses, while you pair your chunkier, more casual booties with shorter skirts.

Sole, Woman

Nine booties to ease you through autumn.

1. The Unofficial NextTribe Lace-Up Boots $180

Here it is: the perfect blend of chic (the on-trend, beloved NextTribe print) and chunky (the combat boot).

2. Bling Booties $128

Short, sassy and shimmery. Perfect for dressing up jeans or for an evening look. 

fall ankle boots

3. Hooked on a Classic  $278

Rugged and cool, these engineer boots by Frye have washed and oiled uppers and are great for leggings and narrow jeans as well as for making a style statement with a short dress.

4. Power Boot $158.95

These pointy-toe booties mean business with a stylish, tulip-shaped topline and tapered heel.

fall ankle boots

5. Patchwork Pleasure $179.95

There is nothing these retro-inspired boots won’t go with (promise!). We love the tonal patchwork upper, the curvy, sculpted heel, and the tapered square toe. By one of our favorite shoe designers, Sam Edelman.

6. On the Fringe $84.99

These fine-fringed wonders by Dingo have a real 70s vibe that fills us with blissful nostalgia.

fall ankle boots

7. Golden Girl $179.95

These scrumptious booties by Vionic, with their embossed crocodile print, feel like something out of Battlestar Galactica, in the best possible way.

8. Buckle Up $79.95

So much to love in these short books by Clarks–the buckle, fat heel, and the hot aubergine color.

fall ankle boots

9. A Double Meow $150

These Lizzo ankle boots by Sam Edelman give us two shots of feline fineness: Classic kitten heels plus a bold tiger stripe. Wear them as a neutral (seriously) because they will add pizazz to anything.

fall ankle boots

Read More: Next Tribe Fashion Survey Results: See How Your Style Stacks Up!

By Kimberly Cihlar


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