Popsugar Fashion Street Style How to Wear Chelsea Boots 12 Elevated and Chic Ways to Style Chelsea Boots 28 April 2023 by Naomi Parris Image Source: Getty / Edward Berthelot As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work. 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 neighbourhood 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 favourite 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. Related: 18 Cool Chelsea Boots We Can't Stop Thinking About Buying This Fall White Chelsea Boots Image Source: nordstrom.com 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. Madewell Kristin Chelsea Boots $91 from nordstrom.com $228 $91 Now 60% off from nordstrom.com Buy Now Shiny Chelsea Boots Image Source: target.com Camille Heeled Boots ($35) Give your outfit an extra sheen with a pair of shiny Chelsea boots with a slight heel. Added bonus? These have waterproof construction to keep your feet dry and warm in the rain. Camille Heeled Boots $35 from target.com Buy Now Heeled Chelsea Boots Image Source: zara.com Zara Heeled Leather Ankle Boots ($169) Give your Chelsea-boots outfit some height with the Cuban heel on these Zara ankle boots. This is a perfect option for dresses that call for a more refined footwear option. Zara Heeled Leather Ankle Boots $169 from zara.com Buy Now Pink Chelsea Boots Image Source: asos.com ASOS Design Gadget Chunky Rain Chelsea Boots ($40) These fashion-forward boots are the epitome of style at an affordable price. The soft pink is a subtle, chic pop of colour, perfect for all your floral dresses this season. ASOS Design Gadget Chunky Rain Chelsea Boots $40 from asos.com Buy Now Coloured-Sole Chelsea Boots Image Source: freepeople.com Free People Phoenix Chelsea Boots ($100, originally $310) Tap into the coloured-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. Free People Phoenix Chelsea Boots $100 from freepeople.com $310 $100 Now 68% off from freepeople.com Buy Now Green Chelsea Boots Image Source: ssense.com Melissa Nancy Boots ($140) Made from sustainable PVC with a foam block heel, these vibrant-coloured boots are comfortable and chic. Melissa Nancy Boots $140 from ssense.com Buy Now Dr. Martens Chelsea Boots Image Source: urbanoutfitters.com Dr. Martens Audrick Leather Platform Chelsea Boots ($200) A long-standing customer favourite, 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. Dr. Martens Audrick Leather Platform Chelsea Boots $200 from urbanoutfitters.com Buy Now Tall Chelsea Boots Image Source: urbanoutfitters.com Alohas Go Getter Leather Tall Platform Chelsea Boots ($240) 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. Alohas Go Getter Leather Tall Platform Chelsea Boots $240 from urbanoutfitters.com Buy Now Orange Chelsea Boots Image Source: ganni.com Ganni's Cleated Midi Chelsea Boots ($495) These cool Ganni boots in "orangeade" easily add the perfect pop of colour to any look. Ganni's Cleated Midi Chelsea Boots $495 from ganni.com Buy Now Blue Chelsea Boots Image Source: chloe.com Chloé Betty Rain Boots ($550) Who said rain boots have to be boring? Chloé's heeled boots, rendered in cool blue, are just the right silhouette for facing rainy days in style. Chloé Betty Rain Boots $550 from chloe.com Buy Now Leather Chelsea Boots Image Source: Net-a-Porter 3.1 Phillip Lim Kate Leather Chelsea Boots ($595) Opt for an elongated upper set with these sleek designer boots. The chunky lug sole adds plenty of structure and stability for rainy weather. 3.1 Phillip Lim Kate Leather Chelsea Boots $595 from net-a-porter.com Buy Now Bottega Veneta Chelsea Boots Image Source: bottegaveneta.com 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 favourite power suit. Bottega Veneta Tire Chelsea Boots $1,450 from bottegaveneta.com Buy Now Chelsea-Boots Outfit Idea: Baggy Pants Image Source: Getty / Christian Vierig 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 Image Source: Getty / Edward Berthelot 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 colours, add another colour in your boots for a nice contrast. Chelsea-Boots Outfit Idea: All Black Image Source: Getty / Christian Vierig Nothing pairs better with Chelsea boots than an all-black outfit. Throw in another colour in your accessories for extra oomph. Chelsea-Boots Outfit Idea: Preppy Uniform Image Source: Getty / Christian Vierig 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 Image Source: Getty / Edward Berthelot A statement-making maxi dress is the easiest outfit fix, but why not take it a step further with a colourful boot? Add a structural bag for a chic, pulled-together finish. Chelsea-Boots Outfit Idea: Mixed Prints Image Source: Getty / Edward Berthelot If you're feeling unconventional, pair your go-to Chelseas with a sleek blazer and layer two prints underneath. Chelsea-Boots Outfit Idea: Monochromatic Image Source: Getty / Christian Vierig When in doubt, go monochrome with your boots for a balanced look. Throw on your favourite-colour sweater, pants, and accessories to match, like this Barbiecore-pink look. Chelsea-Boots Outfit Idea: Floral Dress Image Source: Getty / Edward Berthelot 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 coloured purse for a touch of edge. Chelsea-Boots Outfit Idea: Denim-on-Denim Image Source: Getty / Streetstyleshooters 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 Image Source: Getty / Daniel Zuchnik 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 Image Source: Getty / Christian Vierig Go for the ultimate streetwear vibe with an oversize bomber jacket, a midi skirt, and your favourite boots. Chelsea-Boots Outfit Idea: Sweater Dress Image Source: Getty / Hanna Lassen 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. Street StyleFashion ShoppingMust HavesBoots