How to Wear Ankle Boots

Ankle boots are one of the most versatile types of boots around. Reaching to or just above the ankle, these shoes are simple to wear and suit a range of outfits, including casual and smart casual looks. To rock a pair of ankle boots, you must first select your style. While Chelsea ankle boots are a sleek and simple option, chukkas and other lace-up styles can also appear stylish. Once you’ve chosen your boots, pair them with jeans or trousers and a button-up shirt or sweater. Several styles stand the test of time, however, and deserve a place in your closet. Here’s a quick primer on key styles to invest in, plus, a rundown of our favorites for fall and winter available right now, including our editors’ picks.

Work Boots (or Trench Boots)

Rather than a modern steel toe boot best suited to construction projects, an early twentieth century-style work boot has old school appeal and is tough enough to wear on the daily, but won’t make you like a foreman. Also known as a trench boot, the lace-up, ankle-height, leather style possesses rugged elegance.

Chelsea Boots

Typically produced in smooth leather or suede, Chelsea boots feature elastic side panels that allow for easy slipping on and off. Originated in England, and once a favorite of The Beatles, the ankle-height boots pair easily with jeans or a suit.

Jodhpur Boots

What sets these low-heel, ankle-height boots apart are their signature buckled straps. Jodhpur boots were originally created as an alternative to tall riding boots. Today, we just know that they have some good style swagger.

Desert Boots

Like a lot of boots, desert boots have their roots in the military, and are inspired by British soldiers’ campaigns in North Africa, where they encountered the casual local footwear style. It evolved into the comfortable mens boot we know today with a flat sole and two to three eyelets for shoelaces. A desert boot is known for being super lightweight.

Cowboy Boots

These need no explanation. Not just for wrangling steers on the ranch, the boot typically hits mid-calf, often features an embroidered design and has a significant heel. Leave the spurs on the farm and they’re city appropriate for the fashion-forward dude.

Hiking Boots

Providing protection from the elements, hiking boots offer stability on dicey trails. Today’s best hiking boots make the most of technical fabrics and materials to keep you comfortable in all kinds of terrains.

Brogue Boots

A brogue boot is a suave, showboating lace-up style that’s appropriate for the office or even formal occasions. What sets it apart from other leather, ankle-height boots is the decorative perforations along the seams.

Sneaker Boots

Consider sneaker boots your trusted sports shoes’ winterized cousin. The style boasts hardier outer materials that better hold up to slushy streets than regular sneakers. They’re the perfect option for the sneakerhead who needs a little extra protection from the elements.

Mens Shoes

Casual Combo

Casual Combo

Casual Combo

Casual Combo

Casual Combo

Casual Combo

Casual Combo

Casual Combo

Casual Combo

Low-cut Boots

Low-cut Boots

Low-cut Boots

Low-cut Boots