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.
Come winter, I’m never not dreaming about buying a new pair of boots. And as any typical shopping editor would, I already have a few silhouettes on my radar this season that I’m hoping to either be gifted for the holidays (hint hint, to any of my loved ones) or invest in for myself just in time for the new year. The style at the very top of my wishlist? Chelsea boots, of course. These cool and classic shoes double as the perfect everyday boots that pretty much always look good. Plus, thanks to the style’s durable composition and build, Chelsea boots are also ideal for rainy weather and winter temperatures.
There are also so many different variations of the shoe — from varied colors like brown and white Chelsea boots to leather Chelsea boots, waterproof styles that can withstand the season’s harshest weather, and even a few chunky Chelsea boots that can make any winter outfit all the more eye-catching, the options are truly endless.
To help you find the perfect match, we scoped out the best Chelsea boots for women that are not only trending for winter, but also available to shop from some of our favorite fashion brands like Sam Edelman, Hunter, Steve Madden, Blundstone, Dr. Martens, and more. Ahead, we curated a list of 17 Chelsea boots that you’ll love to wear in any season. Whether you’re looking for something edgy like a pair of black leather Chelsea boots, something practical and easy to walk in like a comfortable pair of Chelsea boots, or perhaps even something that will help to add a fresh pop of color to your winter wardrobe like a pair of pink Chelsea boots, there’s bound to be a style out there that’s just perfect for you. Keep reading to shop our selects and find the perfect boot for you.
— Additional reporting by Krista Jones
:quality(85):upscale()/2023/08/14/672/n/49089156/5f198eba64da438edbe932.95078731_.jpg "Sabrina Carpenter Shows Off Her Abs in an Extreme-Cutout Bodysuit")
:quality(85):upscale()/2025/05/19/981/n/1922564/93076eb0682bb18c994e06.89379902_.png "What to Wear to Lady Gaga’s Mayhem Ball Tour")
:quality(85):upscale()/2025/05/23/715/n/1922564/1e63d6e168309df259d956.72331408_.png "21 Best Memorial Day Clothing Sales 2025")
