Chelsea boots have been a long-standing trend, evergreen even. Fall is when you’ll see them being dusted off and worn with outfits that include pieces like jackets layered over light cashmere sweaters and jeans or a pair of trousers. These boots gained popularity first in the Victorian era, with Queen Victoria often wearing them to go horseback riding. In the 1960s, during the mod era in London, they were dubbed “Chelsea boots” as they gained traction in the Chelsea area of London. Fast-forward to now, and they're not just a trend but an unquestioned classic in the world of shoewear. The style is timeless, with its form-fitting, slip-on technology, designed to support the ankles. Its flat and often platformed sole is made for comfort, while its stretchy panels on the sides make it easy to slip on and off.
The Chelsea boot’s tech hasn’t changed much, but it has gotten some updates throughout the years. Now, the shoe has less of a rounded toe and more of a square-toe shape, and an even skinnier body with an almost sock-like fit. It’s a chic iteration that feels modern and trendy without feeling too trendy. It’s still our classic, just with a slight twist. We can thank brands like Toteme and The Row for that slight change. If you’re on the hunt for a sleek new pair of Chelsea boots, keep scrolling through for an array of fits and colors to add to your closet this fall.
Best Affordable Chelsea Boots
Best Affordable Chelsea Boots: Zara Low Heeled Ankle Boots
Product Specs: Upper made of Polyurethane, lining and sock made of polyester, low heel.
Worth the Investment
Worth the Investment: Prada Double Chocolate Leather Chelsea Boots
Product Specs: Made of calfskin leather, has an upper with elasticized side gusset and pull tab, leather lining, monoblock rubber sole. 16 cm bootleg.
Best Overall
Best Overall Chelsea Boots:
Product Specs: Upper and lining made of leather, sole made of Thermoplastic polyurethane.
More Top-Tier Chelsea Boots
Product Specs: Elastic fabric on the sides, back pull tab, topstitch, block heel, round toe. 2" H x 9" body.
Product Specs: Made of 100% calf leather, outsole made of 100% tread rubber. 1.78" heel x 7" shaft.
Product Specs: Made of 80% leather/20% polyester, rubber/plastic outsole. 1 1/2" heel.
Product Specs: Made of leather and textile upper, and synthetic sole. Includes removable sole. 1 1/4" heel x 1/2" platform x 5 1/2" shaft.
Product Specs: Made of leather, leather lining, sole and insole. True to size, includes elastic sides, size up for half size up.
Product Specs: Made of leather, leather lining and footbed, and textile upper with EVA sole, includes pull tabs, and elastic sides. 2.48" heel x 8" shaft.
Product Specs: Upper made of leather and textile, synthetic lining and sole, includes pull-on elastic gore insets. 1 1/2" heel x 7 3/4" shaft.
Product Specs: Upper and insole made of 100% cow leather, sole made of 60% reconstituted leather, 30% polyurethane thermoplastic, and 10% rubber, lining made of 82% cow leather, 13% polyester, and 5% elastane. Includes a low block heel and elastic sides.
Product Specs: Upper made of leather, lining and sole made of synthetic leather, includes stretch knit insets. 2 1/4" heel x 1/2" platform, 6 3/4" shaft.
Product Specs: Made of black leather. 1" heel.
Product Specs: Upper, insole, and sole made of leather, runs true to size, fits slightly narrow around the ankle, next size up for half size. 2" heel.
Product Specs: Made of leather upper, rubber sole, and lining. 5 1/2" shaft.
Product Specs: Made of Italian cow leather, lining made of Italian lambskin leather. Heel height: 1.7" heel x 3.7" shaft.
Product Specs:
Product Specs: Made of 45% recycled leather, 20% recycled poluester, 20% polyurethane, 15% polyester, lining made of 76% polyurethane and 24% viscose. Includes elastic panels and pull tabs.
Product Specs: Made of leather upper and lining, rubber sole. Includes elastic gore insets. 1 1/2" heel.
Product Specs: Made of shiny leather upper, rubber lug sole, includes a back pull tab, gore elastic sides, and block heel. 2" heel x 7" shaft.
Product Specs: Made of leather, includes a textile upper of recycled polyester, recycled cotton, and a leather and textile lining, and synthetic sole.
Product Specs: Made of a leather upper and Rubber sole.
Product Specs: Made of leather upper and lining. 1 3/4" heel x 6 1/10" shaft.
Product Specs: Made of leather outsole and lining, 75" block heel, includes a side zipper, almond toe shape.
Product Specs: True to size, made of leather and textile upper,textile lining, rubber sole.
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