Men's Boots Guide: Chelsea vs Chukka vs Lace-Up and Brogue Boots
By Oswin Hyde · Last updated 28 September 2026
The short answer: the three essential men's boots are the Chelsea boot (elastic sides, no laces, the most versatile), the chukka (ankle boot with two or three eyelets, relaxed and smart-casual) and the lace-up or brogue boot (more eyelets, sturdier, good for winter and country looks). If you buy one pair, choose a dark brown leather Chelsea boot; add a chukka or lace-up boot second.
Men's boot styles compared
| Style | Features | Formality | Try |
| Chelsea boot | Elastic side panels, pull tab, no laces | Smart-casual to smart; sleek pairs work with suits | Darwin, Jack |
| Chukka boot | Ankle height, 2–3 eyelets, open lacing | Smart-casual | Jefferson |
| Brogue chukka | Chukka with brogue perforations | Smart-casual | Watson |
| Lace-up boot | More eyelets, higher and sturdier | Casual to smart-casual | Graham |
| Brogue (wingtip) boot | Lace-up with a wing-cap brogue toe | Smart-casual, country | Gregory |
| Brogue Chelsea | Chelsea with brogueing | Smart-casual | Harry, Grant (chunky sole) |
Chelsea boots
The most versatile boot: easy to pull on and sleek enough for a suit in black or dark brown leather. Suede Chelsea boots are softer and more casual. Everything you need is in our Chelsea boots guide, with care tips in how to clean Chelsea boots.
Chukka boots
A chukka is an ankle boot with two or three eyelets and open lacing, usually in suede or smooth leather. It is more relaxed than a Chelsea boot and pairs naturally with chinos, flannel and jeans. The Jefferson comes in textured saffiano leather in black and brown; the Watson adds brogue detailing.
Lace-up and brogue boots
Lace-up boots have more eyelets and sit higher, so they feel more secure in bad weather and suit heavier trousers, tweed and denim. The Graham has a lightweight sole; the Gregory has a wing-cap brogue toe for a country look.
Which boots with which outfit
| Outfit | Best boot |
| Suit | Sleek black or dark brown Chelsea |
| Chinos and blazer | Chukka or brown Chelsea |
| Dark jeans | Any: Chelsea, chukka, brogue boot |
| Tweed and flannel | Brogue boot or brogue chukka |
| Winter weekend | Lace-up boot or chunky-sole Chelsea |
Choosing winter boots
- Choose smooth leather for rain; protect suede with a spray and save it for dry days.
- Look for a rubber sole with some tread for wet pavements.
- Treat leather with a water and stain protector at the start of winter.
- Clean off road salt promptly: see our leather shoe care guide.
All our boots use 100% full-grain crust leather from LWG Silver-rated tanneries, with lambskin linings and padded insoles, in UK 7–13. See how our shoes are made.
Frequently asked questions
What is the difference between Chelsea and chukka boots?
A Chelsea boot has elastic sides and no laces; a chukka has two or three eyelets and laces. Chelsea boots are sleeker; chukkas are more relaxed.
Which boots can you wear with a suit?
Sleek black or dark brown leather Chelsea boots with a slim sole.
Are chukka boots smart?
They are smart-casual: ideal with chinos, blazers and flannel, but less formal than a sleek Chelsea boot.
What boots should every man own?
A dark brown leather Chelsea boot first, then a chukka or lace-up boot for casual and winter wear.
Are boots formal?
Sleek leather Chelsea boots can be; lace-up, brogue and chukka boots are smart-casual.
Shop the pieces in this guide: men's boots · Chelsea boots · suede shoes · belts
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