The 14 Best Men’s Chelsea Boots for Any Budget

Chelsea boots are timeless and versatile, and almost every guy should have a pair in his collection.

The Chelsea’s sleek silhouette makes for a nice relaxed boot that you can wear nearly year-round. Obviously, they’re ideal for winter and fall, they’re also great shoes for summer if you want a lighter boot to pair with some outfits.

In addition, Chelseas can be dressed up or down with ease. You can wear them with jeans and a jacket for a casual look, or you can dress them up as part of your winter business casual wardrobe. That’s why the Chelsea is one of our favorite business casual shoes for men.

In this article, we’ll look at 14 pairs of Chelseas at various price ranges. If you’re in the market for a pair, then read on for our list of the best men’s Chelsea boots.

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The UO Dress is made from a soft suede and uses rubber for the outsole. It’s available in chocolate (personally, I think it’s more caramelly), olive and tan.

All in all, if you’re pressed for cash, the UO Dress Chelsea isn’t a bad choice.

#2: Dockers Stanwell

Dockers needs no introduction. You already know they make classic workwear-inspired gear, and their Stanwell Chelsea boot is no exception.

This boot is a rugged take on the classic Chelsea silhouette. Think of it as a casual boot that takes inspiration from work boots. The Stanwell uses Dockers’s proprietary Comfort Zone and NeverWet technologies, meaning this boot repels water while keeping your feet nice and comfortable.

The Stanwell also features full grain leather uppers and a multi-cushioned sole. The light stitching seen on the chocolate and dark tan colorways also adds a nice pop of color.

Since this is a more affordable boot, there are a couple of small quality compromises, like using rubber instead of crepe for the outsole. But given that it retails for $90, you’re getting a solid value for the money.