When it comes to footwear, I have a pretty good understanding of what I like. My shoe collection is centered around classic styles that bridge the gap between casual and formal, in safe and conservative colors and materials. I love the shoes I have, but there are times that I wish I had something with a bit more of a punch to them – something a bit more interesting, a tad more ‘cool guy’ than my normal ‘grandpa’ vibe. Whenever I get that feeling, my mind turns to Chelsea boots.

Chelsea Boots – What to Look For and How to Wear Them

Although Chelsea boots have been around for well over 100 years, they began to gain popularity in the sixties when hip kids in Chelsea (a neighborhood in London) began wearing them. The style made its way to the US on the feet of the Beatles and other pop icons, and they have had a “cool dude” vibe ever since. The most defining characteristic of the Chelsea is the elastic side panels, which allow for easy use. The rest of the boot is usually unadorned, making them sleek and simple. They’re the loafers of the boot world, in a sense – comfortable, easy to take on and off, and a bit more informal than other classic styles.

Chelsea boots tend to come in one of two types – a rougher, chunkier version more akin to a work boot, and a sleeker style more in line with a dress shoe. Although my current wardrobe does skew casual, I find myself more drawn to the dressier style of Chelsea. I find it to be more versatile and more attractive overall, as well as being closer to the original style of the boot.

The classic color for Chelsea boots is black – as made famous by the Beatles and other cool folks – but they come in many color and materials. I like dark colors like brown calfskin or brown suede as alternatives to the classic black, as they also go well with the slick appearance.

One admittedly small detail that I find myself obsessing over is one-piece Chelseas; the shoe is often made from three pieces of leather, but some styles remove the seam below the elastic panel and make the uppers out of one continuous piece of leather (compare this to this). This detail doesn’t make the boot any more durable or comfortable, but it’s a nice piece of craftsmanship that shows attention to detail (as well as going well with the minimalist style), and as such I find myself strongly preferring one-piece Chelseas over other styles.

One great aspect of Chelsea boots is their versatility – their slim profile and rocker connotations help them make a suit look a bit more edgy, while they can also work well with slim chinos or dark denim. They’re a great way to elevate a look and add a bit of urban attitude to an otherwise standard outfit.

Where to Buy Chelsea Boots

Here are some of my favorite chelsea styles, roughly in order from affordable to…aspirational:

Jack Erwin: Good footwear is expensive, and with a niche style like the Chelsea sometimes it makes sense to go for a more affordable option. I’ve found the construction and materials of JE footwear to be just ok, but the styles are usually well executed. Their ‘Ellis’ Chelsea boot is another good option for more entry-level footwear.

Beckett Simonon: This budget-friendly brand keeps prices low by collecting orders before production. Their Chelseas are a bit chunkier than others on this list but they’re still a good option at their price point.

Meermin: the Spanish budget brand just released a one-piece Chelsea in black, and it looks great (shown above). It features a well-balanced shape on the Hiro last, slim rubber sole, and soft leather. For the price it’s pretty much impossible to beat Meermin, especially since they now do shipping and returns through their NYC store for US orders. They also have several other Chelseas available in different styles and materials, which you can see here.

Loake: The budget Northampton brand isn’t as wallet-friendly (or as easy to find) as it used to be due to changes in their US distribution, but they still offer a lot of shoe for the price (especially when on sale). Their Mitchum Chelsea is my favorite from their 1880 line – it’s tall, sleek, and looks great in suede.

Sons of Henrey: this brand-new brand launched with a couple of handsome styles, one of which is a one-piece Chelsea on their almond last (currently on preorder). SoH designed their own lasts, and the result is a very handsome shoe at a good price (shown at the bottom of the article). Made in Spain.

Carmina: The Spanish darling has a number of Chelsea styles, available on many different lasts and in many different materials. While Carmina’s styles are all three-piece construction, you can get one-piece Chelseas through their made-to-order program.

J. Fitzpatrick: Justin has always had bold ideas for shoe styles, and his Chelsea boot is a great example of that (it’s pictured at the top of this article). Not only is it built on a handsome last out of great materials, but it also has a bit of extra style that is unique to this design. The swooping lines of the elastic panel (and one-piece design) make it a great option at this price point. They’re also available in many materials and even made-to-order in whatever style you can imagine.

Crockett & Jones: My favorite all-around footwear company has many styles of Chelseas, although thy all have three-piece construction. Nonetheless, they’re all well-made and have enough styles to make just about anyone happy.

Common Projects: Made famous by their minimalist sneakers, CP has since branched out into many styles of footwear. Their Chelseas are more urban and streetwear-oriented than others on this list, but they do what they do well. I particularly like the black suede ones – a very underrated material that doesn’t get used enough.

RM Williams: Chelsea boots are the cornerstone of this famed Australian brand, so there are many options to choose from. Unfortunately, the price of RMW has gone up substantially in the past few years after their acquisition by Louis Vuitton. The quality is still good, though, and they remain one of the most popular places to get a great pair of Chelseas. They have a huge range of styles, but my favorite is the classic Craftsman (though the suede one is great, too). As far as I know, all are made in Australia and feature one-piece construction.

Zonkey Boot: This small company specializes is modern styles of traditionally-made footwear. Unlike everything else on this list, their shoes are hand-welted (rather than Goodyear welted), which is generally considered superior. Their Chelsea boot style is a looker, and is a great choice for those that obsess over shoe construction.

Viberg: These Canadian footwear experts are most famous for their service boot, but their Chelsea is a popular option as well. The price is high, but they maintain a loyal following and consistently put out handsome and well-made footwear.

Gaziano & Girling: Even though the Chelsea is a classic English style, it seems like many of the top-tier British shoemakers designed Chelseas as an afterthought (I’m looking at you, Edward Green and John Lobb). If I’m going to pay top dollar for a Chelsea, I expect the construction to be one-piece, for starters. The GG Burnham Chelsea, like many of their shoes, is sleek and aggressive – the sharp last and strong lines give it a bold look, and impeccable finishing take it beyond what other brands offer. The one-piece construction looks great, and is frankly something you should expect at this price.

My Personal Favorites

There are many options not on this list, but this should be plenty to get any footwear enthusiast started. For entry-level Chelseas I highly recommend Meermin, for all-around value I love J. Fitzpatrick and Sons of Henrey, and for pie-in-the sky prices it’s hard to beat Gaziano & Girling. What’s your favorite Chelsea?