12 Elevated and Chic Ways to Style Chelsea Boots
While many dramatic boot styles like over-the-knee and extreme platform are popular footwear choices for any occasion, you can never go wrong with a pair of Chelsea boots. Dating back to the first pair made for Queen Victoria in 1837 and named after the chic neighborhood in London, the timeless boot is defined by an elastic side panel and ankle-hugging silhouette that makes it the perfect investment piece. Since then, the style has graduated to innovative design elements, including chunky soles, platform heels, and bold colorways. And with endless options come new and exciting approaches on how to wear Chelsea boots.
Chelsea-boots outfits are easier to style than you think. Versatile as ever, they slip on and off easily and add an effortless cool factor to any look without sacrificing comfort, from your favorite maxi dress with an oversize blazer to a denim-on-denim look. They can be worn practically all year round, from the coldest winter day to a mild April afternoon. If you needed more convincing, some of fashion's most established names have confirmed Chelsea boots' lasting glory as a wardrobe essential. Bottega Veneta's internet-breaking Tire boots have dominated the industry for nearly three years, worn by the likes of Hailey Bieber, Cardi B, and just about every street style star during Fashion Week, editors and influencers alike.
Consider adding Chelsea boots to your shoe repertoire this season, whether you're going for Saturday brunch or a spontaneous nightcap after work. Keep scrolling to shop some of our top Chelsea-boots picks, then read on for 12 fashion-forward ways to create Chelsea-boots outfits regardless of your aesthetic.
White Chelsea Boots
Madewell Kristin Chelsea Boots ($91, originally $228)
If you're a fan of white shoes, these Madewell ivory Chelsea boots are the perfect pair. Go for a neutral khaki tone, or create contrast with all-black separates.
Pink Chelsea Boots
These fashion-forward boots are the epitome of style at an affordable price. The soft pink is a subtle, chic pop of color, perfect for all your floral dresses this season.
Colored-Sole Chelsea Boots
Free People Phoenix Chelsea Boots ($100, originally $310)
Tap into the colored-sole trend with a surprising neutral style this season. The chunky lugged sole is not only durable, but it will also add a surprising contrast to darker-toned separates, from leather jackets to oversize denim.
Dr. Martens Chelsea Boots
A long-standing customer favorite, this Dr. Martens style is the chunky black boot your closet needs. Add some edge to your look by styling this pair with a romantic dress and a leather jacket.
Tall Chelsea Boots
Chelsea boots have graduated to taller silhouettes, and we're obsessed. These boots contain the ultimate cool factor for any look combo, from a pleated miniskirt to jean shorts.
Leather Chelsea Boots
Opt for an elongated upper set with these sleek designer boots. The chunky lug sole adds plenty of structure and stability for rainy weather.
Bottega Veneta Chelsea Boots
Bottega Veneta Tire Chelsea Boots ($1,450)
It's almost impossible to not feel powerful and stylish with the newly iconic Bottega Veneta Tire boots. Made in Italy from black leather with a whimsical rubber sole, these boots are the best option for any look, from your average denim-on-denim to your favorite power suit.
Chelsea-Boots Outfit Idea: Baggy Pants
Play with silhouettes in a half-buttoned shirt styled with high-waisted, printed pants. Finish the look with black Chelsea boots for an extra edge.
Chelsea-Boots Outfit Idea: Slip Skirt
An oversize shirt, a cropped top, and a slip skirt is a statement-making, classic combo that'll always work. If you're wearing bright colors, add another color in your boots for a nice contrast.
Chelsea-Boots Outfit Idea: All Black
Nothing pairs better with Chelsea boots than an all-black outfit. Throw in another color in your accessories for extra oomph.
Chelsea-Boots Outfit Idea: Preppy Uniform
Tennis skirts have been in for some time, and they make the cutest combo paired with chunky Chelsea boots. Add a textured vest if you're feeling preppy.
Chelsea-Boots Outfit Idea: Plaid Dress
A statement-making maxi dress is the easiest outfit fix, but why not take it a step further with a colorful boot? Add a structural bag for a chic, pulled-together finish.
Chelsea-Boots Outfit Idea: Mixed Prints
If you're feeling unconventional, pair your go-to Chelseas with a sleek blazer and layer two prints underneath.
Chelsea-Boots Outfit Idea: Monochromatic
When in doubt, go monochrome with your boots for a balanced look. Throw on your favorite-color sweater, pants, and accessories to match, like this Barbiecore-pink look.
Chelsea-Boots Outfit Idea: Floral Dress
Florals for spring are indeed groundbreaking, but they're elevated even more with a chunky Chelsea boot. Work in your go-to jean jacket and colored purse for a touch of edge.
Chelsea-Boots Outfit Idea: Denim-on-Denim
The Canadian tuxedo is a classic styling approach when it comes to any season, but feel free to mix it up by adding a hoodie and boots to match.
Chelsea-Boots Outfit Idea: Power Suit
Dress down your sleekest power suit with a white pair of Chelsea boots. Incorporate a chain bag that coordinates perfectly.
Chelsea-Boots Outfit Idea: Bomber Jacket
Go for the ultimate streetwear vibe with an oversize bomber jacket, a midi skirt, and your favorite boots.
Chelsea-Boots Outfit Idea: Sweater Dress
Pairing a sophisticated piece with edgy, black Chelsea boots is so chic. Plus, the combination of a cardigan dress and this boot is ideal for any occasion. Layer over a turtleneck for structure.