For a touch of Nineties elegance, Prada’s brown suede Chelsea boots offer a rounded square toe that avoids pressure and ...

A suede ankle boot is always a winter wardrobe necessity, but instead of sky-high stilettos, make yours a kitten-heeled ...

The 2976, which has been manufactured since the ’70s, is the brand’s hard-wearing Chelsea boot. The pair is handsome and understated, made from a smooth leather that’s more matte than patent ...

Chelsea boots are a classic for a reason: They never go out of style. Sure, designers might introduce a few unexpected twists ...

Why We Love It: These shoes encapsulate all of the traits we look for in a pair of Chelsea boots. They’re made of soft, slightly shiny leather, have strong proportions and smooth lines ...

Cole Han's Berkshire Lug Water-Resistant Chelsea Boots are still on sale for just $110 when you use the code HOLIDAY at ...

Shoes are what tie any outfit together, though, and right now, you can grab these rugged but handsome Chelsea boots from Ugg ...

Winter short boots blend warmth, style, and practicality, making them essential for cold weather. From the sleek Aldo Marthia ...

The Silva boots are fully waterproof Chelsea boots with equal parts style and toughness. The brand uses Italian full-grain pull-up leather for these handsome Chelsea boots. Full grain leather is ...

Learn more The leather Chelsea boot has been a fall staple since Victorian times, when it was still a style worn by horse riders. These laceless boots are characterized by their elastic sides and ...

Upgrade your everyday ankle boots with this cowboy-inspired take that’s currently on sale. They’re made with shiny black faux ...