How to Wear Chelsea Boots

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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.