The Most Comfortable Designer Chelsea Boots for Men to Shop Right Now

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These boots were definitely made for walking (and showing off).

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When it comes to fall footwear, the Chelsea boot is unrivaled in its comfort and stylish looks. Their signature design includes two elastic gores and a pull tab—the rest is up for artistic interpretation.

Like most timeless pieces, this one, too, has stood the test of time thanks to its functionality. Fashion historians attribute the first pair of Chelsea boots to Queen Victoria’s shoemaker—J. Sparkes-Hall who claimed in 1851 that the monarch “walks in them daily.”

The name “Chelsea boots” (they were first called Paddock boots) though didn’t come until the 1950s when a group of young creatives in London dubbed “ The Chelsea Set” started wearing them regularly (Chelsea, here, refers to the King’s Road area in the English capital). The Beatles were notoriously fans of the Chelsea boots except that theirs were fitted with Cuban heels—a type of heel that is slightly tapered at the back.

The rest, as they say, is history.

Now, check the most stylish pairs of Chelsea boots to add to your shoe closet this fall.

Brunello Cucinelli Chelsea Boots


Brunello Cucinelli Chelsea Boot

Rich suede in dark brown and a classic Chelsea silhouette make these boots a fall staple. The twin elastic gores guarantee perfect fit and the loop on the back makes it easy to put the boots on. Wear them with a pair of slacks and a blazer for a modern look.

To buy: $895, nordstrom.com

Gucci Quebec Leather Chelsea Boots


Courtesy Saks Fifth Avenue

True to its flamboyant aesthetic, Gucci’s take on the classic Chelsea boots is an extravagant one. They sport a pointy-toe silhouette and spiked details on the soles. One of the two side gores is also given an ornate treatment—it features three adjustable gold-tone buckles. For style inspiration, look no further than this Jared Leto look.

To buy: $1,250, saksfifthavenue.com

Fendi Square-Toe Leather Chelsea Boots


Courtesy Saks Fifth Avenue

Logomania at its finest! Fendi’s stylish Chelsea boots have the company’s signature double F logo printed all over their backs. They are crafted from flexible leather for maximum comfort and feature two elasticized gores. While the soles sport a square shape at the front, the boot itself has a classic round-toe design.

To buy: $850, saksfifthavenue.com

Salvatore Ferragamo Darien Leather Chelsea Boots


Courtesy Saks Fifth Avenue

These dressy Chelsea boots are the epitome of Italian craftsmanship. They are made from genuine leather sporting the signature cross-hatched look of Saffiano leather. We are also fans of the loop design —instead of popping up from the back, it is constructed as a tab laying fairly flat for a more stylish silhouette.

To buy: $895, saksfifthavenue.com

Tom Ford Men's Stuart Lug-Sole Suede Ankle Boots


Courtesy Neiman Marcus

Need a sturdy pair of stylish boots? Tom Ford has you covered. This pair of classic calf suede Chelsea boots features lugged rubber soles for maximum stability even when the weather is not cooperating. Stretchy gores and a pull tab complement this must-have pair of footwear.

To buy: $1,190, neimanmarcus.com

Frye Paul Leather Chelsea Boots


Courtesy Saks Fifth Avenue

Frye’s Chelsea boots are cut for a below-the-ankle fit and sport a comfy almond-toe silhouette. The deep brown hue of the leather adds a bit of a vintage vibe to the boots and the padded soles make them the perfect everyday option for fall.

To buy: $298, saksfifthavenue.com

Giuseppe Zanotti Chelsea Boots


Courtesy Zappos

Inspired by the Chelsea boots of the 50s and 60s, this pair by Giuseppe Zanotti sports a classic Cuban heel for some added flair and height. The leather upper has been given a scaled treatment for a luxe crocodile-like look.

To buy: $669, zappos.com