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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.


When you’re busy and you just want to toss on a pair of shoes and go, it’s hard to beat some nice Chelsea boots. We’ve talked about them in the past, and while we still like the list we came up with, many of those boots are now unavailable. That’s why we’ve refreshed our choices—once again available for immediate purchase, and as timelessly styled as ever.

1) Buttero: Tanino Suede Chelsea Boot

Chelsea-Boots---Five-Plus-One 1) Buttero: Tanino Suede Chelsea Boot

Chelsea boots are inherently comfortable due to their slip-on nature, but Buttero has kicked it up a notch with their Tanino Suede Chelsea boots, which feature a sneaker-style cup sole for added comfort. While this design choice will certainly be divisive, it certainly matches with the casual nature of the shoe given both the rest of its design and Buttero’s choice of leathers. Made in Italy, these boots will surely become a favorite in short order.

Available from $185 at End Clothing.

2) Viberg: Shell Cordovan Chelsea Boot

Chelsea-Boots---Five-Plus-One-2)-Viberg-Shell-Cordovan-Chelsea-Boot

Viberg’s Chelsea Boot Pattern is certainly not for everyone, but it’s hard to deny that they look damn good when made from shell cordovan. Available in three different hues and with all the bells and whistles, these boots are far from cheap; however, if you’re looking for your next pair of everyday boots and don’t mind paying for all those bells and whistles, it doesn’t get any better than this. They feature Viberg’s Goodyear welted construction rather than the stitchdown construction that has long been synonymous with the brand, but this choice and the use of a ridgeway sole perfectly matches the rest of the boot.

Available for $1280 at Viberg.

3) Cheaney: Godfrey

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If you are looking for a pair of Chelsea boots than can easily be dressed up or down then look no further than Cheaney’s Godfrey boot. Available in a wide selection of suedes, these sleek boots feature a closely-cut Goodyear welt, full leather-lined interior, and the made-in-England construction quality that the brand is known for.

Available from £204 (~$250USD) at Cheaney.

4) Feit: Handsewn Chelsea

Chelsea-Boots---Five-Plus-One-4)-Feit-Handsewn-Chelsea

While dressy chelsea boots are all well and good, sometimes you just want something on the chunkier side—and when that’s the case, it doesn’t get any better than Feit and their Handsewn Chelsea. Available in brown and blacked-out colorways, these boots pack some serious heft; with their 360° leather welt, full leather midsole, and rubber-topped leather outsole, you get a lot more rigidity than you would expect form these bamboo-shanked boots.

Available for $795 at Blue Owl.

5) R.M. Williams: Craftsman Chelsea Boots

Chelsea-Boots---Five-Plus-One-5)-R.M.-Williams-Craftsman-Chelsea-Boots

It would be a crime to discuss Chelsea boots without mentioning R.M. Williams, and so we won’t. Their Craftsman Chelsea Boots are about as classic as they come with their simple design, slightly squared toe, dual pull loops, and rustic leather outsole. While these are certainly boots that I’d wear, and wear hard, they could definitely be worn in a dressier environment if the mood strikes.

Available for $495 at Mr. Porter.

Plus One — Corthay: Bella Python

Chelsea-Boots---Five-Plus-One-Plus-One---Corthay-Bella-Python

Exotic leathers really, really aren’t my thing. That said, it’s hard to deny the inherent beauty present on Corthay’s Bella Python Chelsea Boot. Made from, you guessed it, python leather, these short-stack Chelsea boots are as sleek, chiseled, and elegant as any Chelsea boot. While they’re definitely a “sometimes” shoe that is really what the Plus One spot is all about. And at over six-thousand dollars I can’t expect anyone will wear these shoes for anything other than the most special of occasions.

Available for $6160 from Leffot.