Now that the leaves are finally falling and the temps are dropping to a crisp, autumn cool, it’s time to break out your warm boots. Not just any boots will do, though. While we’re obsessed with leather knee high boots, there’s another style that has stood the test of the time. The classic Chelsea boot, of course!
18 Loose Denim Pants That Are More Flattering Than Skinny Jeans — Under $50
The best Chelsea boots boast high quality materials that hold up in rain, snow and dirt. They also feature elastic on the side to make the boots easy to slip on and off. Bonus points for pairs that are available in a mix of heel heights and styles. Plenty of high quality Chelsea boots can be found for under $200, and we rounded up our favorite picks below. Ahead, see the best Chelsea boots on Amazon made for walking everywhere this fall!
The 8 Best Chelsea Boots on Amazon
- Best Overall: The Sam Edelman Laguna Chelsea Boot features that classic Chelsea boot design we know and love. These boots have a pull-on design that makes them easy to slip on and off. Plus they’re waterproof to protect feet from the elements. Pair them with jeans or a skirt this fall — $150 on Amazon!
- Best Everyday Chelsea Boot: If you love the look of classic Chelsea boots but want something that isn’t bulky, try these ankle boots. The Naturalizer Darry Booties are crafted with water-repellent leather and a suede upper with sustainable lining and a round toe, making them perfect for the rain and snow. Shoppers report the boots are so comfortable that they’re excellent to wear as an everyday shoe — $140 (originally $170) on Amazon!
- Best Chunky Chelsea Boot: These stunning boots are under $50 and don’t sacrifice style or details. Shoppers praise how easy they are to slip on and off and the surprisingly comfortable fit. Pair these with stylish socks for a warm and cozy look — $50 on Amazon!
- Best for Winter Weather: With temperatures dropping quick, it’s extra important to seek out boots that withstand winter’s harsh elements. These ones from Toms are made with a durable textile lining and insole. Plus, they come in several colors — $69 (originally $140) on Amazon!
- Best Suede Chelsea Boot: The Ariat Fatbaby Twin Gore Western Boots check all of our boxes: Exceptional craftsmanship, timeless style and superior comfort. While these boots boast more of a western fit, we know you’ll love styling them with your favorite fall jackets and jeans — $88 (originally $110) at Amazon!
- Best for the Office: Shoppers “love wearing these wedges for walking stability,” and it’s clear why. These Chelsea boots boast an elevated yet supportive wedge heel for all-day comfort — $34 (originally $40) on Amazon!
- Best Waterproof Chelsea Boots: Who said rain boots can’t be stylish? These waterproof Chelsea booties are 100% waterproof and boast a faux fur lining to keep feet warm while warding off rain, snow and ice — $30 (originally $40) at Amazon!
- Best Platform Chelsea Boots: Sperry is known for exceptional footwear, so it makes sense that its iteration of the Chelsea boot is undeniably rich mom chic — $90 at Amazon!
These Boots Were Made for Walking! The Comfiest Fall Boots on Amazon
Not what you’re looking for? Check out more Chelsea boot styles and don’t forget to shop Amazon’s daily fashion deals here!
Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!
