Menswear often oscillates between extremes; going from bulbous Balenciagas on the street to whole-cut oxford shoes for black tie events. As such, it can be easy to overlook a versatile classic like the humble Chelsea boot. However, it would be remiss not to have at least one pair — but ideally two; one black and one dark brown — of Chelsea boots in your wardrobe, with their streamlined silhouette and hardwearing nature allowing them to traverse across multiple dress codes with ease.
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And while it’s been a while since the style’s heyday — with Chelsea boots peaking during the British mod movement of the 1960s and being co-opted by The Beatles — they stand steadfast in the face of fleeting trends. Equally as at home with slim-cut suiting as they are with jeans and a chore coat, Chelsea boots are an essential all-occasion footwear style.
What is a Chelsea boot?
A laceless slip-on shoe style, Chelsea boots are characterised by their slim silhouette, low heel, and above-the-ankle height and are easily identifiable by their signature elastic or vulcanised gusset side panels and pull tabs. Traditionally, Chelsea boots comprise two core elements; the vamp and the quarter, each of which are constructed from a single piece of leather and are united by the aforementioned side gusset. Chelsea boots originally featured rounded toes, however, contemporary iterations have also seen the rise of squared and pointed toes, with the accepted dictum being that “the pointier the toe, the dressier the shoe”.
History of Chelsea boots
Chelsea boots can be traced back to the Victorian era, with Queen Victoria’s shoemaker widely credited with having invented the style. In 1851, J. Sparkes-Hall, bootmaker for Queen Victoria, conceived the style for use by equestrians — at the time, they became known as ‘paddock boots’ and were worn by both men and women. It was said that Sparkes-Hall created the boots with elasticated inserts on either side to make it easier for the Queen to pull on and off.
By the 1950s and 1960s, the hardwearing paddock boots gained popularity in Swinging London and became the footwear of choice for the stylish Chelsea crowd; resulting in the name Chelsea boots. The newly named style was seen on the likes of The Beatles, The Rolling Stones, Mary Quant, and Jean Shrimpton, cementing their place in the fashion world.
Cut to now and Chelsea boots remain a failsafe footwear option, with their streamlined silhouette and hardwearing properties making them a favourite for farmers and fashionistas alike.
What makes a good Chelsea boot?
Chelsea boots are typically made with leather or suede (however some manufacturers opt for animal-free materials) and generally come in neutral colours like black, brown, and tan. As with anything, not all Chelsea boots are made equally. The best Chelsea boots are those that are crafted with Goodyear welt construction, which extends the lifespan of your boots by allowing them to be resoled once worn out.
How to wear Chelsea boots?
A true all-rounder, the appeal of the Chelsea boot lies in its versatility. Unlike Oxfords which sit definitively in the formal category or chunky sneakers which are unable to break past semi-casual dress codes regardless of how you style them, Chelsea boots — depending on their silhouette, colour, and make — are able to flit between dress codes with ease.
That said, styling is crucial when it comes to wearing Chelsea boots.
- For casual outfits, opt for brown, tan, taupe, or grey Chelsea boots in leather or suede (the latter is more laidback). Pair with knitwear, slim-cut (not skinny!) denim with the hem just covering the top of the boot (you can pin roll or cuff your jeans or trousers to achieve this), and a corduroy shacket or chore coat for a play on blue collar style.
- Dark brown and grey suede Chelsea boots are ideally suited to smart casual outfits; pair them with dark wash denim or tapered trousers, a thin roll neck knit and a chunky crewneck sweater. For the more sartorially adventurous, hues like oxblood, burgundy, or forest green in brush-off leather can inject a welcome dose of colour into your outfit. Far from being hard to style, they also work well with denim and a chunky knit.
- Black, deep burgundy, or dark brown leather boots are an apt fit for business casual outfits. Simply team them with tailored trousers, an oxford or roll-neck shirt, and a blazer.
- When it comes to semi-formal outfits, stick to leather Chelsea boots in dark brown or black leather. For a refined touch, black patent leather never fails. Team with a suit in a shade of dark brown, grey, charcoal, or black.
The best Chelsea boots for men in 2023
1. Crockett & Jones Lingfield Boots
Founded in Northampton, England, a town famous for its footwear heritage, Crockett & Jones knows how to make a good pair of Chelsea boots. Constructed with a Goodyear welt, the Crockett & Jones Lingfield Boots are decidedly dressy, with their tapered square toe contributing to a streamlined, elegant look.
Goodyear welt: Yes
Price: £575 (approx. $1100AUD)
2. R.M. Williams Comfort Craftsman Boots
With its roots in the outback but many of its contemporary customers in the concrete jungle, R.M. Williams is adept at traversing all manner of terrain, bridging the gap between casual and formal with ease. Known for their quality craftsmanship, Australian-made credentials, and hardwearing nature, R.M. Williams boots are made to last. Crafted from a single piece of leather, the R.M. Williams Comfort Craftsman Boots feature a low heel and square toe, lending them a slightly dressy touch.
Goodyear welt: Yes
Price: $649AUD
3. Saint Laurent Wyatt Chelsea Boots
There is no perhaps better encapsulation of the Hedi Slimane era at Saint Laurent (RIP Yves Saint Laurent) than this pair of Chelsea boots. Anchoring the majority of the black, skintight looks on impossibly thin, heroin chic-esque models, the impossibly sleek Saint Laurent Wyatt Chelsea Boots are characterised by their slim silhouette, ankle-gripping elastic, and almond toe. While they’re available in a low-heeled iteration, the stacked heel is a must for that grungy, bohemian vibe.
Goodyear welt: No
Price: $1625AUD
4. Myrqvist Elfvik Chelsea Boots
A casual Chelsea boots style courtesy of Swedish footwear company Myrqvist. The Goodyear welted Elfvik Chelsea Boots are crafted from water-repelled brushed suede from British tannery Charles F. Stead and designed with heavy wear in mind. Their studded rubber sole makes them ideally suited to hard wear and harsher climates, making them a solid winter boot choice.
Goodyear welt: Yes
Price: $349USD (approx. $530AUD)
5. Carmina Chelsea Boots 80809
Spanish shoemaker Carmina never misses. The Carmina Chelsea Boots 80809 put a fun twist on the style; crafted from marbled burgundy leather (with colour-matched gussets) using traditional shoemaking techniques — and naturally, Goodyear welt construction — they feature a long, tapered silhouette with an elegant rounded toe.
Goodyear welt: Yes
Price: $690AUD
6. Solovair Cherry Red Rub-Off Vegan Hi-Shine Dealer Boot
Ah, the Chelsea boot’s rougher cousin. Essentially the same as a Chelsea boot, save for the extra piece of material (and different name), the Solovair Cherry Red Rub-Off Vegan Hi-Shine Dealer Boot is made from two-tone rub-off vegan leather. The hand-finished colouring combined with the slightly thicker sole lend it a tough, streetwear-ready feel.
Goodyear welt: Yes
Price: $329AUD
7. Common Projects Full-Grain Leather Chelsea Boots
Footwear label Common Projects transposes its minimalist design codes onto the humble Chelsea boot. Crafted from pebbled leather and featuring a wider silhouette and rounded toe, these boots recommend themselves as the perfect daily stompers. Like all Common Projects creations, the Full-Grain Leather Chelsea Boots feature the brand’s signature ten numbers emblazoned in gold on the heel, which denote the shoe’s size, style, and colour.
Goodyear welt: No
Price: £518 (approx. $992)
8. Velasca Lampionèe Chelsea Boots
Defined by clean lines and classic cuts, Italian footwear label Velasca’s shoes are built to transcend time and trends. The Velasca Lampionèe Chelsea Boots are crafted from full-grain leather and feature a heavy-duty Vibram rubber sole to ensure they’re able to withstand inclement weather, while the brogued details on the front add a touch of old-world style.
Blake construction: Yes
Price: $640AUD
9. Aurélien City Chelsea Boots
The Aurélien City Chelsea Boots fuse the classic style with the aesthetics of a driving shoe to create a louche, laidback hybrid. Made in Italy from oiled suede, their durable rubber soles ensure comfort while their relaxed aesthetic works to elevate casual outfits.
Goodyear welt: No
Price: $659AUD
10. Church’s Leicester
Northampton stalwart Church’s can always be counted on for a stylish yet hardworking pair of boots. The Church’s Leicester leans into the rugged equestrian heritage of the Chelsea boot with a lightweight, casual style that features a chunky rubber sole with enough grip to withstand even the rainiest of days.
Goodyear welt: Yes
Price: €980 (approx. $1630AUD)
11. Morjas The Chelsea Boot
Spanish-Swedish brand Morjas know utilitarianism needn’t come at the cost of style. Take its interpretation of the Chelsea boot, which ditches superfluous details in favour of a sleek silhouette with a marginally wider toe box to ensure wearer comfort. The grippy rubber sole prevents you from slipping around in wet weather while the low heel gives it enough gravitas to pair with tailored pieces and raw denim alike. It’s all about balance.
Goodyear welt: Yes
Price: $349USD (approx. $530AUD)
12. Oak Street Bootmakers 5504 Chelsea Boot
Crafted from a single piece of Horween Chromexcel leather, the Oak Street Bootmakers 5504 Chelsea Boot takes on a rugged appearance, with a rounded toe, tapered vamp, and studded rubber role. Designed to stretch with time and wear, it’s recommended to go down half a size. The unique Chromexcel leather is set to develop a rich patina as the years pass, adding character and interest to your boots.
Goodyear welt: Yes
Price: $348.60USD (approx. $529AUD)
13. Scarosso Giancarlo Marrone
Made in Montegranaro, Italy, Scarosso shoes offer impeccable craftsmanship at a surprisingly accessible price point. Handcrafted using the Blake method, the Scarosso Giancarlo Marrone injects a welcome dose of colour into the Chelsea boot, by way of a dark green elastic gusset which acts as the ideal complement to the brown leather. With a low heel, elongated silhouette, and tapered toe, the Scarosso Giancarlo Marrone is well suited to semi-formal and even formal occasions.
Blake construction: Yes
Price: $545AUD
14. Blundstone 500 Chelsea Boots
Blundstone and R.M. Williams enjoy a healthy rivalry down under, however for us, the answer is simple. Shorting stocks followed by a cocktail at Opera Bar? R.M. Williams. Mucking stalls in the rain before a dinner out? Blundstones. A reliable, no-nonsense style that can take a beating and look good doing it, the Blundstone 500 Chelsea Boots — available in buttery soft leather or suede — are a failsafe option that stand the test of time.
Goodyear welt: No (cemented construction)
Price: $234.95AUD
15. George Cleverley Jason Leather Chelsea Boots
A decidedly refined take on the Chelsea boot, but we’d expect no less from British shoemaker George Cleverly. The George Cleverley Jason Leather Chelsea Boots are cut slightly lower, lending them a dressy appearance.
Goodyear welt: No
Price: £747.77 (approx. $1432AUD)
16. Celine Cruiser Chelsea Boots
You either love them or hate them. Celine boys are born, not made.
Goodyear welt: No
Price: £1061.46 (approx. $2032AUD)
17. Viron World 1997 Black Apple
An atypical take on the Chelsea boot, the Viron World 1997 Black Apple is crafted from apple leather and features a thick lug sole that gives it a grungy, streetwear aesthetic. Style with cropped, raw-edge denim or juxtapose them against tailored trousers.
Goodyear welt: No
Price: $378AUD
18. Melvin & Hamilton Martin 5
For those who aren’t afraid to stand out. Crafted from blue vegetable-tanned leather, these Chelsea boots feature brogued detailing throughout with a contrasting toe cap and heel patch in brown leather.
Goodyear welt: No
Price: €229.90 (approx. $382AUD)
19. Kleman Tonnant EC
French footwear label Kleman offers a robust take on the style with the Tonnant EC. Crafted from hard-wearing suede, these Chelsea boots feature a durable rubber lug sole that’s both slip- and abrasion-resistant. Made with workers in mind, they’re able to hold up against any task.
Goodyear welt: No (cemented construction)
Price: €229.90 (approx. $382AUD)
FAQ
Men can style Chelsea boots for occasions ranging from casual to semi-formal. For a more casual outfit, pair suede boots in a light colour like grey or tan with straight cut denim, a t-shirt, and a chore coat. For a more elevated look, opt for leather boots in a shade like black, dark brown, or oxblood and team with tailored separates or a suit.
Despite sneakers dominating the men’s footwear conversation, Chelsea boots remain a wardrobe stalwart for their timeless nature and ability to traverse between dress codes. As such, every man should own at least one pair of Chelsea boots.
Your jeans should never be tucked into your Chelsea boots, nor should they completely cover them. Opt for either slightly cropped jeans or pants with no break.
Words by T. Angel
Feature image courtesy of Velasca
