How to Wear Chelsea Boots Like a Fashion Pro This Spring

Shoe trends may shift from retro-inspired suede sneakers one moment to pointed-toe slingbacks the next, but knowing how to wear Chelsea boots stylishly has stood the test of time (and TikTok-fueled fads) as a hallmark of a true fashion pro. That’s because those in-the-know understand that it’s a classic for a reason: The best Chelsea boots have a way of complementing any outfit or aesthetic, they can be worn in any season, and they’re one of the few shoes that can blend comfort with polished sophistication. Basically, Chelsea boots are—and always have been—that girl.

Despite their versatility, Chelsea boots aren’t just any ankle boot: The unisex style is defined by its elastic side panels, which allow it to seamlessly slip on and off. Other than that, the footwear is entirely customizable. The wardrobe staple can range from contemporary chunky soles à la Dr. Martens to Prada’s sleek black leather signatures to statement-making stompers via Bottega Veneta’s brightly colored platforms.

But to better understand the Chelsea boot’s popularity, we have to first time travel back to the Victorian era: English shoemaker J. Sparkes-Hall designed the now-iconic silhouette in 1837 for OG horse girl Queen Victoria, who sought a sleek and secure style that fit into a saddle’s stirrups. (Before you ask “who’s Chelsea,” the boot’s name stems from the Chelsea neighborhood in London, where the style was created.) Nearly two centuries later, the slip-on style is still going strong.

Today, a pair of Chelsea boots can level up just about any outfit, which makes them a versatile wardrobe investment with unlimited sartorial possibilities. For a casual look, dress them down with your favorite pair of jeans, be it a baggy wide-leg cut, classic straight-leg jeans, a trendy barrel silhouette, or nostalgia-inducing skinny pants. You can also welcome back the indie sleaze aesthetic with a chunky black Chelsea boots or contrast the shoe’s outdoors-y feel with a dark brown pair and a breezy, flowing maxi skirt. Leather chelsea boots also pair well with structured outerwear, like oversized blazers and trench coats. And because they work with just about any hemline, they’re a good transitional shoe between seasons.

So without further ado, we’ve compiled outfit ideas and style tips that work for any aesthetic. Here’s how to wear Chelsea boots in 2025 according to the fashion pros.

With a dress

With boho chic making its grand return to the runways, the art of pairing a flowing maxi dress and a chunky shoe is back in full force. Though Chelsea boots can lean more utilitarian, they’re also versatile enough to couple up with brightly patterned midi or mini dresses, satin slips, or your favorite LBD. For some sartorial bonus points, experiment with colorful boots in a shade that matches or complements your dress’s pattern. Chilly outside? A leather jacket or vest is a nice balance.

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Farm Rio Delicate Tapestry Midi-Dress

$265

Nordstrom

$265

Shopbop

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Journee Collection Tru Comfort Foam Kenova Booties

$120 $55

Nordstrom Rack

With a maxi skirt

Your favorite Chelsea boots don’t have to collect dust in the back of your closet while waiting for sweater weather to return. Transition your boots from winter wear to springtime by experimenting with textures and patterns, like mixing a tiered maxi skirt with a suede Chelsea boot or contrasting a flowy lace maxi with a button-down shirt and chunky leather.

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Siliteelon Fitted Button-Down Shirt

$23

Amazon

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Intimately Kiss Kiss Half Slip

$78

Free People

With an oversized blazer or jacket

Really good blazers are one of the best things to come from the “office siren” trend, especially when they’ve got ‘80s-inspired power shoulders to match the bulk of a platform Chelsea boot. An oversized blazer—whether it’s accompanied by equally baggy black jeans or disguising a mini skirt—adds a structured workwear touch to the slip-on boots. Upgrade the blazer and boots combo by accessorizing with some eye-catching socks or statement tights. Alternatively, the utilitarian feel of an oversized military-style coat is a good balance to the durable boots. The twist comes from a dainty slip dress worn beneath.

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Cider Faux-Leather Zipper Jacket

$33

Amazon

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AllSaints Harlee Lug-Sole Chelsea Boots

$379 $78

Nordstrom Rack

With a suit

On a similar wavelength, wearing Chelsea boots with a full suit is a workwear power move. Dress shoes like stilettos can only get you so far (literally), and the sleek, pointed-toe boots fit right in with tailored trousers and a fitted jacket. Plus, it’s an office-friendly style that has that formal look without sacrificing comfort for your nine-to-five.

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Prettygarden Work Pants

$42

Amazon

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Everlane Lug Chelsea Boots

$238

Everlane

With jeans

To be fair, jeans go with everything—but a Chelsea boots and denim combo always delivers. The good news? The denim silhouette is truly up to the wearer with these shoes: Throw on a pair of slouchy, wide-leg jeans to show off just the top of the boots, or make your shoes the star of the show by styling them with a slim-fit look or cropped jeans. As the denim pendulum starts to swing back toward skinny cuts, I’ll be channeling Harry Styles circa 2015—specifically Long Hair Harry, IYKYK—who rocked a pair of Chelsea boots (and skinny jeans) like none other.

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Madewell Stovepipe Jeans

$138 $50

Madewell

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Steve Madden Evan Boots

$150 $110

Steve Madden

With a trench coat

Rain or shine, Chelsea boots and trench coats are a match made in fashion heaven. A statement trench—whether buttoned to the top, belted at the waist, or casually showing off the full ‘fit—pairs well with the slip-on footwear, a combo regularly seen on the streets during this past New York Fashion Week. It works with any timeless beige trench and brown suede boots, or even a head-to-toe leather look complete with a longline black leather trench and platform Chelsea boots. That latter ensemble may veer into The Matrix territory, especially if you add a pair of black sunglasses, but the ‘90s are back.

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The Drop Noa Trench Coat

$46

Amazon

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Blundstone Classic Chelsea Boots

$200

Zappos

With a mini skirt or shorts

Your instinct might be to style Chelsea boots with pants, but they’re a nice balance for shorter hemlines, too. Balance the neutral tone of the shoes with a simple T-shirt, cardigan, or button-down up top, then feel free to go wild with a patterned skirt in between that matches your personal style. When the weather gets colder, keep the same formula—all you need to do is swap the top for a turtleneck and add tights.

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