Chelsea Boots – Five Plus One

Five Plus One is our weekly series of buyer’s guides. We pick a specific category and dig up five great options along with one that’s a little outside the norm.

While we’ve written about Chelsea boots many times before, our past lists are, for the most part, outdated. That’s why we decided to put together a new selection of some of the finest Chelsea boots currently available. While not all wardrobes work with every pair of boots, we hope you’ll find a pair that you can envision in your collection.

1) Cheaney: Godfrey D in Mocha

Chelsea-Boots---Five-Plus-One 1) Cheaney: Godfrey D in Mocha

If you are looking for a pair of boots that are perfect for all around wear, whether dressy or casual, then Cheaney’s Godfrey D in Mocha is an excellent option. Made with a beautiful a dark brown calfskin, these boots feature a low profile rubber sole that offers excellent comfort and traction while looking nearly indistinguishable from a leather outsole (at least when being worn).

Available for $490 from Leffot.

2) Grant Stone: Chelsea Boot in Crimson Chromexcel


Grant Stone does a great job of offer their own take on classic styles, and it shows in their Chelsea Boot in Crimson Chromexcel. Their aim was to land right between the two styles of chelsea boots, workwear and dress, which is something they have done quite well. Featuring Horween’s Chromexcel leather and a studded rubber outsole, these boots are easy to pair with your favorite jeans or your office chinos.

Available for $325 from Heddels Shop.

3) Viberg: Chelsea Boot 2050 in Milkshake Calf Suede


Viberg’s Chelsea Boots may not have the same iconic appeal classic Service Boots, but this iteration in Milkshake Calf suede is arguably one of the most attractive suede Chelseas available right now. Featuring the aforementioned Milkshake Calf Suede, beige elastic, and natural leather outsole, these shoes form a tonal masterpiece that will only get more attractive with wear.

Available for $860 from Blue Owl.

4) John Lofgren: Chelsea Boots in Black Chromexcel


John Lofgren’s Chelsea Boot might not be as easy to dress up as some of the other boots on this list, but if you’re looking for a pair strictly for casual wear then these are a great option. Made from Chromexcel with Japanese horsehide lining, these boots are finished with a 360° stormwelt, Vibram 430 sole, and quality construction throughout.

Available for $1035CAD from Lost & Found.

5) Unmarked: Chelsea Toro in Heavy Black Suede XL


Unmarked makes some truly unique boots, but their Chelsea Toro in Heavy Black Suede XL is the most interesting of the lot if you ask me. Made from black suede with a calfskin lining, these blacked-out boots feature black stitching, a black welt, a black midsole, and most importantly a black, foam ripple sole. While these shoes will always remain strictly in the casual category of footwear, and I can’t imagine they’ll work with everyone’s wardrobe, they’re definitely one of the coolest pairs of Chelseas on the market.

Available for $350 from Unmarked.

Plus One – Butts and Shoulders: Chelsea Boots in Natural Veg Tan


While there are a ton of truly unique Chelsea boots out there, Butts and Shoulders continues to do what they do best: make top quality, undyed natural veg tan boots. This time around they’ve improved things even further by utilizing a natural crepe outsole, ensuring that the whole boot ages gracefully. While the black elastic might not be everyone’s top choice, there is something about that combination of undyed vegtan and black that just works for me, so I can’t say I’m not a fan.

Available for €399 from Cultizm.