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