There are few footwear options more iconic or versatile than the classic Chelsea boot. Whether you’re all about statement outfits or prefer a more minimalist aesthetic, we’ve yet to find a fashion trend that isn’t elevated by a pair of these timeless boots.
Aside from being comfy and stylish regardless of platform height, Chelsea boots are fuss-free thanks to a handy little feature that makes pulling on these all-weather shoes so convenient. Unlike other ankle boot styles, Chelsea boots have an elastic gore — that’s fashion talk for the stretchy bit — on either side of the ankle to allow for the easy process of pulling them on or slipping them off. Like Chelsea boots themselves, the gore can blend in seamlessly or feature a pop of color that makes it stand out.
When it comes to what clothes you can wear with Chelsea boots, the sky is really the limit. Because they’re not skintight, you can tuck your pants into Chelsea boots for a streetwear-inspired look. Chelsea boots also hit the sweet spot on the ankle that makes them look equally cool with cuffed or cropped jeans and wide-leg or puddle-style pants.
Dressed up or down, Chelsea boot outfit options are nearly limitless, but we were able to narrow down the best of the best to just 14 looks for you to try this fall.
Dress Up Leggings
Adding Chelsea boots and a blazer is a quick way to dress up a pair of leggings. Classic black is always in style, but you can level up your fashion game by choosing a pair of two-toned Chelsea boots and creating a color-blocked look.
Embrace Bright Colors
The rugged treads on a pair of platform Chelsea boots look even better in a bright color. To avoid your boots getting lost in a sea of color, we recommend letting them act as the statement piece by including pops of brightness in your coordinating accessories and outerwear, rather than going fully monochromatic.
Toughen Up a Slinky Dress
A pair of chunky, rugged Chelsea boots brings a bit of toughness to even the slinkiest of maxi dresses. The longer the dress and chunkier the boot, the more enhanced the mermaid-style flare of the silhouette will be. You can opt for a more dramatic look or keep things subtle with an ankle-length dress like Ellie Delphine.
With Utilitarian Layers
You can never go wrong with an all-black outfit, especially when the weather calls for structured layers. Chelsea boots are a perfect choice for fall and winter weather, bringing a utilitarian ruggedness to cold-weather basics like high-waisted trousers and a peacoat.
Tone Down a Gown
Add some street-style edge to a gown or long dress that might otherwise feel too formal with a pair of shiny patent leather Chelsea boots. As an extra twist for experimental fashion girlies, pick a pair of boots in a contrasting, eye-catching color.
Spice Up Denim-on-Denim
Denim-on-denim looks beyond the classic Canadian Tux have slowly but steadily gained street style cred. Embrace your inner streetwear star by tucking baggy jeans into a pair of Chelsea boots and tossing on a hoodie and oversized denim jacket.
Pick a Boot That Pops
The gore of a Chelsea boot doesn’t just make them a breeze to pull on and off, it also functions as a source of fashion inspiration. A vibrant gore can brighten up an otherwise monochromatic fit or tie-in statement accessories. Dealer’s choice.
Adding metallic footwear is a great way to spice up casual separates, especially neutrals and denim pieces. To make silver or gold Chelsea boots stand out even more, tuck long pants into your boots or, better yet, wear ankle jeans with distressed hems.
Show a Sliver of Sock
Add a pop of your personal aesthetic to the timeless and casual oversized button-down and leggings combo by wearing black Chelsea boots and a pair of brightly patterned socks. The flash of color at your ankle adds an expected layer of personal style without compromising the streamlined look.
Try Earth Tones
Calling all Virgos! Earth-tone lovers don’t need to feel pinned down to black when it comes to Chelsea boots. A pair in brown or tan suede is equally fashion-forward, especially when worn with similarly colored trendy fall staples like maxiskirts and bomber jackets.
Pick a Platform
The stitching and sole details on Chelsea boots lend themselves to colorblocking, especially when they’ve got a chunky platform’s worth of style real estate. If you’ve got vibrant statement accessories you love, we think it’s definitely worth searching for a pair of matching platform Chelsea boots.
Ground Mixed Prints
A pair of classic black Chelsea boots and a matching black bag can create cohesion in an outfit that features mixed or clashing prints and colors. Rather than trying to make every piece in this Chelsea boots outfit go together, we recommend leaning into controlled chaos. Don’t worry about clashing—the boots bring it all together.
Pair With Tall Socks
Create the illusion of fall’s trending thigh-high boots without the hassle — or expense — of finding a pair of boots that fit perfectly. To keep this look streamlined from the waist down, we recommend thigh-high socks that blend seamlessly into your Chelsea boots.
If they’re matte or pebbled leather, opt for wool socks. If they’re patent leather, try a fabric blend with a touch of synthetic sheen.
Add an Edge to Pastels and Prints
Thanks to their silhouette, Chelsea boots rarely read as overly saccharine, making them the perfect footwear foil for ‘fits that are otherwise ultra-sweet and feminine. Case in point: this look that features an adorable blend of colorblocking and gingham.