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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.


We have previously taken at a look at Laceless Boots, and this week we have the chance to delve a little deeper into one particular style of slip-ons: the Chelsea boot. Their history is a bit unclear, although it appears that the first Chelseas appeared in Victorian England, when advances in rubber technology allowed for their signature stretch. They’ve seen several reinterpretations, as both Australian work boots and the favorite footwear of the Beatles.

Their timeless design make them perfect for dressing up or down, and their slip-on style make them an excellent choice if you are looking for a quick pair of shoes to throw on.

1) Common Projects: Chelsea Boot in Dark Grey Suede

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First up is this pair of Dark Grey Suede Chelsea Boots from Common Projects. Some people might consider Common Projects to be a bit too high-fashiony, but their styles are spot on — in this case a low profile Chelsea boot with a closely trimmed sole. Unfortunately, that closely trimmed sole doesn’t come without drawbacks. Although it’s impossible to say without looking at them in person, this pair of boots is likely uses Blake or Cemented construction.

Available for $517 from Need Supply.

2) Meermin: Chelsea Boot in Dark Brown Calf

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If you are looking for a Chelsea boot that is slightly more on the formal side then it’s hard to look past Meermin. Their Chelseas are not only formal enough to wear in business casual situations, but also feature rubber soles when you want to dress them down. They’re shown here in brown calf, but are available in a range of leathers.

Available for $220 from Meermin.

3) R.M. Williams: Comfort Craftsman in Brown Suede

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To many, the R.M. Williams’ Chelsea Boots are quintessential. They certainly have a different look than many of the Chelsea boots that we see stateside, with their taller heel and narrow, elongated waist. They’re constructed with only a single seam, located at the back, which helps to keep the profile nice and clean.

Available for $495 from Mr. Porter.

4) Carmina: Simpson Chelsea Boots in Black Calf

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Like Meermin, Carmina‘s Chelsea Boots are quite formal — especially this model in Black Calf. It has a sleek toe and tapered waist, which really helps to sell this boot as a piece of formal footwear. At over twice the cost of Meermin’s Chelsea, some might be deterred by Carmina’s price — but the extra cost certainly shows in both construction and material quality.

Available for $533 from Carmina.

5) Buttero: Chelsea Boots in Cuoio

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Buttero is probably better known in the shoe game for their sneakers, but that doesn’t mean their boots are anything to scoff at. Their Cuioi Chelsea Boot is certainly different from many other Chelsea boots on the market. It’s shorter and the back of the boot comes in closer to the ankle, which completely changes the profile of the shoe. It might seem a bit too pre-distressed to some, but that’s part of its charm.

Available for $530 from Buttero.

Plus One – Rider Boot Co: Fritz Chelsea Boot in Waxed Kudu Gaucho

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Rider Boot consistently releases interesting boots, but sadly there is only room on this list for one: the Fritz Chelsea in Waxed Kudu Gaucho. Although the design of the boot is fairly standard, the leather really sets it apart from all others. It’s made from CF Stead’s Kudu leather, which is tanned in England with hides sourced from culling operations in Africa. Since the hides are from wild animals, you can really see all the natural imperfections exemplified.

Available for $450 from Rider Boot.