The Most Stylish Waterproof Chelsea Boots (2023)

I love these chunky Sam Edelman boots.

They have a rugged sole and sleek suede uppers. The combination of the edgy sole and sleek form-fitting shaft are so stylish! 

And best of all, they come in a range of fantastic colors.

I raved about a pair of chunky Dolce Vitas in this post, but then I discovered they also make a waterproof version!

These sporty boots have a sleek almond toe and shiny rubber finish. I love the contrasting colors and chunky soles!

Blundstone is famous for its sturdy boots.

If you’re looking for waterproof protection and warmth, you’ll want these Blundstone chelsea boots.  They’re made from leather with a thinsulate liner for extra warmth in the winter.

They have firm tread, are sturdily built and fit so nicely they’re easy to take on and off.

These are one pair of boots that can handle anything!

Chaco’s chelsea boots will keep you equally comfortable in city streets as in the mountains.

These slip-on boots are made of full grain leather and have been completely sealed and waterproofed, down to the seams. It might be pouring outside but your toes will be comfy, warm and dry!

I love that the chelsea boots also have removable cushioned footbeds and that the soles are rubberized and non-marking with extra traction.

If you love spending time outdoors, no matter the weather, you’ll love Chaco.

Nisolo makes stylish chelsea boots that are sustainably made.

This pair strikes the perfect balance of comfort and fashion. It has a custom rubber sole that’s thin and lightweight, so they’re very easy to walk in.

The leather (or suede) options are all waterproof and the round toe silhouette makes them wearable everyday, in any outfit.

Sorel makes fantastic shoes.

These brown chelsea boots are no exception. Made from full grain leather, they’re sleek and durable and will have you feel like you’re walking on clouds.

The slip-on boots are also fully waterproof, so they’ll keep you dry in the slickest conditions. Finally, the cushioned footbed make them supremely comfortable and snuggly!