Ankle Boots

Step out in style with a pair of elegant Ankle Boots for men from Stylight. The ankle boot is a versatile piece of footwear, and it fits superbly with everything from smart suits to casual jeans. This selection of ankle boots for men has all kinds of different colors for you to choose from, from earthy shades and classic black hues to more intriguing and eye catching monochromes. Comfortable and handsome, our ankle boots for men are made by top designers.

The Best Ankle Boot-Bottom Pairings

Some pairs are a match made in wardrobe heaven. Cooler than jeans and a tee, and more casual than a suit and tie, we deem the following ankle boot, trouser combos the best of any and all fashion pairings.

Jeans

No matter if they’re dark washed and straight-legged or bright white and skinny, team your favorite denim with a killer ankle boot to match.

Why: From the rowdy and rebellious to the prim and proper, the best of the stylish best have donned denim perfection with their favorite footwear. We think it’s time you paired the beloved bottom with ankle boots that are just as cool.

How: Find a cut and color that fit your style best. Are you clean cut and casual? If so, find comfort in a pair dark blue, slim fit jeans and a suede ankle boot. Looking to don something a bit more daring? Roll the hems of an inky black skinny and style the bottoms with studded, leather ankle boots.

Cropped Trousers

Hitting just at your ankle and floating casually above the neck of your boot, there’s something so polished and proper about a perfectly cropped trouser and ankle boot combo.

Why: The clean cut of a cropped pant offers a playful juxtaposition against the edgier appearance of an ankle boot.

How: Turn up the contrast and team a cool colored cropped trouser in blue, olive or burnt orange with a sinister, black ankle boot. Go for texture and find a boot made of lush velvet or buttery leather.

Suits

Bring a cool kid look to your suits with the help of a bad boy ankle boot.

Why: Unleash your inner rocker and get noticed by HR for all of the right reasons. The boot works as an unconventional office-appropriate option that brings more personality to your corporatewear than those loafers ever could.

How: Keep things neutral and pair a matte black ankle boot with a bespoke, gray suit. Not only will the monochrome look play in your favor, you’ll also be able to get the most wear out of a black shoe.

Challenge monogamy and pair your ankle boots with any of these three bottoms for a dapper look that can’t be beat.

Finding your ankle boots' perfect match starts with finding the perfect ankle boot.

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