Chelsea boots are the British and Australian counterpart to the American penny loafer. Seems like an odd comparison (loafer vs. boot) but they’re laceless, versatile, and a complete classic that most men in the U.K. will at some point acquire and wear to death. Chelsea boots are easy to dress up or down, and they’re available in a wide range of leathers and lasts. The elastic sides may not be to everyone’s taste, but there’s no denying the comfort that they bring. The Chelsea boot is a great alternative to structured chukka boots, loafers, monk straps, and even sneakers. Here are 10 pairs of Chelsea boots that run the range from informal to dressy…
Inexpensive, suit-worthy Chelsea Boots. Nordstrom nailed the shape of these beaters. They could be a little taller, and the sole is cemented, but at this price, who’s complaining? Not everyone buys into the buy-once-keep-forever mindset. Ships and returns for free.
H&M’s Chelsea Boot is surprisingly nice for (just) under a Benjamin. The rubber soles are glued and the leather is not the highest quality (all caps now… “PREMIUM QUALITY”), but they should last for a few years with minimal care. They’d make an excellent work-appropriate rain boot. H&M’s shoes are included in their in-store and online sales so it may be worth waiting for these to drop in price. Also available in tan and brown.
Jack Erwin’s newly-released Chase Chelsea boot ticks all of the right boxes. The Blake Stitched sole, minimal stitching, and classic round toe last give the boots a sleek, elegant look. The walnut full grain is a mid-brown that can be dressed up or down. The black version is dressy enough to be worn with an informal suit. More on Jack Erwin here and here.
The Petworth is a classic British Chelsea boot on a slightly elongated last. These are from Loake’s “Shoemaker” line so the quality will not be as high as the previously-reviewed Loake Kempton chukkas or shoes from Allen Edmonds. That being said, they’re easy to dress up or down, and frequently on sale at Pediwear and Herring. Use the promotion code “freeship” at Pediwear to get free shipping to the United States. Try “TWEET10” at Herring for 10% off.
The Coltham Chelsea boots are manufactured for Herring by Loake in their Northampton, England factory. Made to the highest 1880 standard, the Coltham boots come in a casual brown waxy leather (shown), a dark brown cigar suede, and a dress black calf. The Colthams are on the same 026 last as the Loake Kempton chukkas. The Goodyear welted sole has a rubber fore to add a bit of grip during unpleasant weather. Also worth trying TWEET10 for an extra 10% off at checkout. Many thanks to Robert W. for the tip!
Barker’s Pembroke Chelsea boots may just be the perfect dress boot for nasty weather. The wider last and Dainite rubber soles nudge these boots into the casual end of the Chelsea spectrum, but they still look sleek and stylish. The best deal on these boots is currently at Pediwear. Use the code “freeship” for free shipping. Also available in tan calf.
ShoePassion is a relatively new player in the world of high-end men’s shoes. They’re not as tried and proven as some of the more established brands, but they offer unique styles on sleek lasts. The 620 is a love-it-or-hate-it cap toe Chelsea with a round toe. Goodyear welted and made of smooth box calf.
Sanders is one of the longest-standing middle class British shoemakers. Founded in 1873, Sanders has evolved to become a specialist in Goodyear welted dress shoes and exceptionally durable boots for police, military, and special forces. Their shoes are designed to be exceptionally comfortable for long periods of wear. The Thirsk is a casual, durable Chelsea boot in dark brown waxy leather. It’s meant for everything from navigating along uneven European lanes to hiking through the woods.
Helloooo nurse! Cheaney makes some darned fine boots. The Threadneedle is the quintessential British dress Chelsea. It’s sleek, sexy, and slightly elongated. Classic silhouette in a soft but long-lasting calf leather. Cheaney’s boots are incredibly comfortable after a couple of days of wear. The most suit-worthy Chelsea boots on this list.
The Cheslea boots of Australia. R.M. Williams are frequently worn by Australian politicians, actors, businessmen, and stylish men of all ages. StyleForum member Sator created a comprehensive guide to the many Chelsea boots that R.M. Williams offers. The Craftsmen is the most popular style. The chisel-toe will not appeal to everyone. Many consider these to be the best Chelsea boots in the world.
Cole Haan isn’t known for fantastic quality, but these might become a go-to as the weather turns terrible. The leather is a dark, smooth brown, and while waterproof, doesn’t look plastic or synthetic. The last is sleek and slightly elongated. The contrast stitching and navy gore give these boots a bit of pop that stands out in a good way. Synthetic sole has some grip for wearing in inclement weather. Ships and returns free through Nordstrom. Many thanks to reader Aaron V. for sending in the style tip on these.
About the author: Chris (aka Bruschetta) is an America-born university researcher and teacher based in Glasgow, Scotland, as well as a moderator on Threads. His sense of style is inspired by a childhood dressed in Ivy league trad, and the fact that he is enormously well bred.