Pretty much every guy can rock sneakers. And most men own a pair of dress shoes. Boots, however, are a heavily underutilized form of footwear, and we think it’s because not many people know where to start. That’s a shame, since men’s boots come in such a wonderful range of designs, heights, materials, etc.

In this essential guide, we’re outlining the different types of men’s boots and giving some pointers on how and when to wear them: 

Men’s Boots: Chelsea Boot

Height: Ankle

Laces or Pull-on: Pull-on

Style: These close-fitting boots have an elastic side panel, and they are typically made of suede. Men and women first wore Chelsea boots in the 1800s Victorian era. Then in the ’60s, these boots made a re-emergence in British mod fashion when they became the Beatles’ footwear of choice.

How to wear it: The Chelsea boot is semi-casual but trendy. Wear them with  jeans and a blazer, sports coat, trench coat or leather jacket.

Men’s Boots: Cap Toe Boot

Height: Ankle

Laces or Pull-on: Laces

Style: Cap toe boots feature a straight-seamed cap over the toes. These leather boots are considered more formal and can be worn with dress slacks, chinos, nice jeans, and blazers.

How to wear it: You can wear cap toe boots with a winter suit and overcoat. Think: swank Sherlock Holmes.

Men’s Boots: Wingtip Boot

Height: Ankle

Laces or Pull-on: Laces

Style: These low-heeled leather boots are similar in style to cap toe boots. Instead of a straight seam across the toes, though, wingtips feature a “W” shaped cap that extends toward the heel. Wingtip boots have decorative perforations along the seams. Originally called “brogue shoes,” wingtips used to be considered a strong outdoor shoe, made from untanned leather. They’re now often worn in offices, though still considered more casual than cap toe boot shoes.

How to wear it: Wingtip boots are semi-formal. You can wear them with a flannel suit or with dark jeans, a collared shirt, and a sweater.



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