21 Seriously Cool Pairs of Chelsea Boots

It’s no secret that Chelsea boots have gone from trendy shoe to wardrobe staple — which is why you NEED to get yourself a pair as soon as possible. Chelsea boots are known for their casual, easy-to-wear style and their signature elastic panel at the ankle. They look rad with jeans, awesome with dresses and [best of all] they’re comfy. And for city dwellers, that’s key! Just because Fall hasn’t quite begun doesn’t mean you can’t add to your boot collection, so here are 20 cool pairs of Chelsea boots to help get you started.

Need Supply New Kid Penny Teaser Bootie, $207

Need Supply New Kid Penny Teaser Bootie

Anthropologie Albo Bootie, $140

Anthropologie Albo Booties

Zara Fur Ankle Bootie, $100

Zara Fur Ankle Bootie

Penelope Chilvers Nelson Pull On Bootie, $501

Penelope Chilvers Nelson Pull On Bootie

Zara Flat Elastic Chelsea Boot, $100

Zara Flat Elastic Chelsea Boot