Men's Chelsea Boots for a Great and Luxurious Look

Men's Chelsea Boots for a Great and Luxurious Look

Men's Chelsea Boots

When it comes to a shoe that nails both smart and casual dress codes, there really isn’t anything quite like Chelsea boots. Typically made from leather or suede, they have all the appeal of formal footwear but are engineered in a way that makes them easier to get on and off than a slip-on trainer (that elasticated panel and tag at the back ain’t there for show, you know).

The Chelsea boot began its life in the Victorian era and, rumour has it, was first made by Queen Victoria’s personal bootmaker. Fast forward a few years and it was later adopted by the cool kids of Chelsea (hence the name), with some more A-list adopters in the form The Beatles and then The Rolling Stones. Today, almost every stylish man owns a pair, including modern men’s style icons Ye and Brooklyn Beckham.

And so, we’ve compiled our edit of the very best Chelsea boots you can buy as we step into Autumn. From classic iterations by some of our favourite high street brands to striking suede slip-ons from Saint Laurent, here’s our pick for every taste and budget…

What are the most comfortable Chelsea boots for men?

In truth, whatever pair of leather boots you might choose to purchase, there’s going to be a break-in period. The real question is, what is the best way to avoid blisters with your ankle boots? Well, our advice would be three-fold. Firstly, when transitioning from sneaker to Chelsea, you need the right socks; something thick to give you some added protection on those all-important friction points. Secondly, you’ve got to keep stretching out those uppers. If you don’t have a shoe horn to hand (although we’d recommend purchasing one), a large can or even some scrunched-up newspaper should do the trick.

And lastly (and most bizarrely), Dr Martens lovers have claimed that if you have freezer space, popping your Chelseas among the frozen peas and chicken nuggets with a sandwich bag full of frozen water in them can stretch out the leather just enough to leave some wiggle room once they’re back on again. But we urge - nay beg - you to freeze wisely.

What are the best brands for Chelsea boots in 2024?

You won’t find anything in this list that isn’t of high-quality craftsmanship... but when it comes to style, there are two main ways you can go with a Chelsea. There’s the classic style; think your Church’s and your Jones Bootmakers, the kind that full-grain, rich calfskin, or something that could be considered a ‘dress Chelsea boot’.

On the other side of the spectrum, you’ve got your wonkier options. Something often accompanied by a heftier price tag and a thick lug sole. We’re picturing the Bottega Veneta ‘Tire’ Chelsea, of course.

Scroll on for GQ's pick of the best Chelsea boots for men in 2024…