You know the seasons are shifting - and that maybe you’re getting older - when the idea of slipping into a pair of perfectly polished Chelsea boots for the first time in months, sounds about as satisfying as getting a full eight (preferably nine) hours of sleep.
Originally crafted for Victorian horse riders who needed quick and easy footwear removal, Chelsea boots have evolved into the ultimate winter staple. Sleeker than hiking boots, sharper than hobnails, and tougher than desert boots, a well-made pair of Chelseas should be the cornerstone of your cold weather shoe collection. Or, if you’re anything like me, 15+ pairs will constitute that cornerstone.
Which brings us to my curated selection of the 15 best Chelsea boots of the new season - whether you’re looking for just one, or plan to expand your collection to Teo levels of stupidity.
1 | The Sporty Ones
Designed by Italian label Sunnei, the just-visible haemoglobin hue of the tire tread sole contrasts beautifully with the smart chestnut upper of these boots, making them great for smart(ish) occasions. Like the winter wedding of someone you don’t know all that well. Or an interview for a job you'd quite like, but aren’t all that bothered about getting.
2 | The Ones From the Future
Prada’s wintry answer to the square-toed Razor loafers of last season, these below-the-ankle Chelsea boots would look best worn with a sharp-edged black suit, with trouser hems which finish just above the pull tab. I can imagine Jeff Goldblum wearing these.
3 | The Casual Ones
Part-high-top trainer, part Chelsea boot, these extra-comfortable numbers from Marni are a slightly diluted take on a Rick Owens clodhopper (and all the more wearable for it).
4 | The Slinky Ones
You know how much I love the shape of Loewe’s Campo last, so I don’t need to explain to you why I love these boots so much BUT I REALLY LOVE THEM.
5 | The Everyday Ones
Finished with a hybrid sneaker sole, these sharp black Chelsea boots from Dunhill fall neatly in line with the British brand’s freshly chiselled aesthetic.
6 | The Ones for Rainy Days
I tried on a pair of these Camper boots, finished with clever galosh toes, in Palma airport a few months ago. It felt far too hot to be buying a pair of Chelsea boots at the time, even though they were drastically reduced, so I left them on the shelf. It’s a decision I’ve regretted ever since.
7 | The Entry Level Ones
A sturdy pair of squared-off black Chelsea boots from high street stalwart, Arket. Don’t expect them to be too comfortable and accept they’ll never be mistaken for the similar(ish) pair made by Jil Sander, and you’ll get along just fine.
8 | The Ones to Wear for Subtle Sex Appeal
Sturdy, shiny, solid. You’d be forgiven for mistaking these for a regular pair of boring black Chelsea boots, if you didn’t take a closer look at the additional transparent layer on the base of the sole. It’s a subtle design trick which elevates the boots from pedestrian to perfect, making them a strong offering from Sean McGirr’s first collection for the storied British brand.
9 | The Ones to Wear with White Jeans
Classic, easy, relatively affordable. There’s very little not to love about these chestnut suede Chelsea boots from Sunspel. Made in Portugal, they’d look great with some slim white jeans. A look which would also work well…in Portugal.
10 | The Ones to Wear with Pyjamas
I’ve had a weird fascination with these quilted Chelsea boots from Hungarian brand Nanushka since they first hit the market a few years ago. They kind of remind me of an aardvark’s snout, in a good way. Great with some slouchy dark denim from Y/Project, these.
11 | The Dependable Ones
Sturdy and solid, these classic chocolate suede Chelsea boots from Prada-owned, British brand Church’s will last you a lifetime (as well they should, for just shy of £1000).
12 | The Excellently Obnoxious Ones
Like something Krusty the Klown might wear on a weekend visit to Pizza Express with his estranged daughter, these bulbous-toed Chelsea boots from Bottega Veneta are things of intentionally ostentatious brilliance.
13 | The Dressy Ones
God love Giorgio Armani. The only man in the world who could ever make a pair of ultra-slinky midnight blue velvet Chelsea boots look anything other than, well, a bit creepy.
Wear with blue tailoring, safe in the knowledge that you look like a billionaire Italian Octogenarian indulging in a spot of apres ski.
14 | The Ones to Hike the Escalators of Harrods
Chunky and truculent, these heavy tread Chelsea boots from Burberry are one of the current high points in the beleaguered British brand’s offering.
15 | The Best Chelsea Boots I’ve Ever Worn
No one makes a more comfortable - or more elegant - pair of shoes than John Lobb. Expensive, yes, but you’ll want to wear them forever and they’ll last even longer than that. Perfect with everything from tweed tailoring to weekend denim and maybe - maybe! - a pair of tracksuit bottoms (from Issey Miyake).
If you’re enjoying The Closet please consider upgrading to a paid subscription (just click on the button below). It’s the cost of a coffee (or less), once a month and it will help me to continue producing this newsletter each and every week.