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The Ultimate Guide to Men's Boots: The 6 Boot Styles You Should Know & Tips On How To Wear Them

There comes that point in the season when shoes no longer cut it. That's when snow-stomping, ankle-shielding, manly leather boots step in. From Chelsea to chukka to dress boots, there are plenty of options out there to keep you warm and moving this fall/winter season.

The Chelsea Boot

Chelsea boots are characterized by no laces, ankle-high height and a close fit. This unadorned and elegant elastic-sided slip-on boot says a lot without saying too much.

How to wear the Chelsea boot

The Chelsea boot works just as well with a suit in a formal look as it does with jeans or chinos in a casual outfit. If you're wearing it with a suit though, make sure the cut of the trousers complements the slim, clean lines of the Chelsea boot.

The Chukka Boot (or the Desert Boot)

The chukka boot is an ankle boot with two or three lacing eyelets. The sole of the chukka boot is traditionally made of leather. Crepe-soled chukkas are called desert boots.

How to wear the chukka boot

The more traditional suede version of the chukka boot is a casual staple in your boot arsenal. In beige or tan, it is ideal for weekends paired with jeans or chinos. The chukka boot in dark brown or navy can be a great choice to complement a smart weekday look.

The Dress Boot

Dress boots are sleek, perfect looking formal boots with laces. Their clean, elegant appearance says they're designed to be worn with suits and dress pants in formal looks.

How to wear the dress boot

Well this one is self-explanatory. Wear dress boots when you're putting together a dressy look. However, you can also rock the sleek dress boot to contrast with a casual outfit.

The Brogue Boot (or the Wingtip Boot)

Similar to brogue shoes, brogue boots are boots with perforations and, most commonly, a wingtip toe cap.

How to wear the brogue boot

Brogue boots are dressed up enough to be worn with suits, yet the perforated wingtip design makes them casual enough to go with jeans or cords.

The Casual Boot

The casual boot is a workhorse, the laced-up, ankle-high handsome staple in your fall and winter casual wardrobe. A perfect casual boot has a rugged, worn-in look that says they don't mess around and they get the work done.

How to wear the casual boot

This one is a no-brainer. Casual boots lend themselves perfectly to casual outfits, so wear them with jeans, chinos and wool trousers. However, the casual boot is also a great footwear choice if you want to spice up a formal suited look.

The Work Boot

Most work boots are lace-ups made from leather, usually with a thick rubber sole and often with steel toecaps. They are comfortable, practical, durable and just stylish enough to stay on your feet during the colder months.

How to wear the work boot

Wear the work boot with a pair of khaki chinos or tough denim and a knit cardigan for an outdoorsy, adventure-ready look.

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