Despite constant trend turnover, the best Chelsea boots are too versatile a wardrobe mainstay to ever actually leave our shoe rotation. Originally popularized by fashionable Brits (including the Beatles) in the ’50s and ’60s, the classic ankle boot has since evolved into the icon we know and love today, with a slip-on design, stretchy side panels, and chunky soles. And thanks to its durable craftsmanship and city-friendly walkability, it’s no wonder that stars like Taylor Swift and Daisy Edgar-Jones rely on this essential year-round—especially when the temperature drops.
As we stride into 2026, it’s time to ditch the notion that the millennial-beloved shoe is outdated; yes, they may have defined the early 2010s thanks to Alexa Chung and Saint Laurent, but the style goes far beyond skinny jeans. On the contrary, Chelsea boots offer a foolproof addition to a slew of outfits, from officewear looks to casual, pared-down ensembles. Whether you decide on a flowy maxiskirt and a button-down shirt or wide-leg jeans and a slouchy top, one thing’s for certain: The boots inject the perfect amount of edge without compromising the “chic” in any look. These are the absolute best Chelsea boots to shop for this season and beyond, from trendy suede pairs to budget-friendly Amazon bestsellers.
The best Chelsea boots for women, at a glance
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Best leather Chelsea boots
While boot trends come and go, there’s never any shortage of smooth leather Chelsea boots. Why? They stay true to their versatile roots, equipped with ample arch support, rugged outsoles, and stylish hues that will remain in your closet for years. If you’re on the hunt for a classic, consider a pair of work boots from Australian standard-bearer Blundstone. (Multiple Glamour editors will tell you that they’re worth the investment.) Black Chelsea boots also make for the perfect going-out shoes—and luckily, they’re available in a variety of dressy, statement-making options, including stompers from Coach and heels from Dream Pairs.
Best suede Chelsea boots
In case you missed it: Suede boots are the style du jour, beloved for their velvety texture that strikes the perfect balance of function and fashion. (You get bonus points if they fall into the season’s biggest color trend, chocolate brown.) Want your soft and supple ankle boots to make a statement? Pair camel-colored Chelsea boots with straight-leg trousers for an effortless French-girl feel, or opt for a neutral hue, like ash gray, for a pared-down look.
Best shearling Chelsea boots
Chelsea boots with cozy shearling lining will have you stomping through cold weather in comfort and style. The cushy yet wearable shoes are primed for peak wintertime and available in a bevy of fun options: fur-lined platforms from Sam Edelman, fuzzy Doc Martens, waterproof foldovers via Hunter. The key to rocking a pair of lined Chelsea boots is not to overthink it, and you can never go wrong with a chunky sweater and baggy jeans. Throw a down coat on top for a full-on cozy ensemble.
Best waterproof & slip-resistant Chelsea boots
Water-resistant Chelsea boots are a winter essential because, depending on the style, they’re both fashion-forward and impervious to inclement weather, impromptu showers, and slippery sidewalks. L.L.Bean, Hunter, and Barbour offer time-honored favorites that will literally keep you grounded when the weather gets gross. But perhaps our favorite pair here hails from Sorel, which offers chunky, interesting silhouettes that can counter any forecast while adding an unexpected twist to your look; just look at those vibrant peek-a-boo rubber soles.
By India Roby
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