The capital is known for its laid-back take on dressing, and just about every major trend to come from the city in the last few years has championed comfort first. First, there was normcore (the minimalist's dream tailored wardrobe). Then, we flirted with gorpcore (a celebration of the great outdoors), and who could forget cottagecore (the cardigans, puff sleeves and floral dresses ideal for the countryside). This summer was undoubtedly all about barbiecore (I don't think that one needs explaining). Whichever tribe you fell into, British women have always known how to make functional feel fashionable. But one piece, in particular, manages to span across trend and time and is once again having a moment that we would be remiss to ignore.
This sartorial item revisits every year like your favourite cousin and ties together many looks and aesthetics you already have in your wardrobe. With bare legs and a little sock showing at the top, coming out under a pair of jeans or with a good thick pair of high denier tights - they're an overachiever.
In the last few months, Londoners have invested heavily in puffer coats, shearling jackets and ribbed-knit dresses, but the one item you can guarantee you'll see stomping around the streets of the Big Smoke are chunky Chelsea boots. Apparently, when the temperatures drop, we all reach for the same thing—pull-on ankle boots with a flatform or heavy tread sole that wouldn't look out of place on a hike. They are comfort-meets-cool, all-in-one easy shoes.
The famous and ubiquitous Ganni chunky boots ran so that others could walk. Now, thanks to more releases of The Row's Zipped 1 Boots, Bottega Veneta's Lug Boots, and Prada's Monolith Boots, Londoners are ditching laces and stiletto heels for something a little more stylish, and the answer is a comfy sole and chunky silhouette worn with everything from pretty dresses to leather leggings. Plus, it's the coolest way to update the "blazer + tee + jeans" uniform we lived in all summer. (Just add an oversized shearling jacket.)
So for the ideal finishing touch to your next autumnal outfit, keep scrolling to shop the best chunky Chelsea boots on the market now and see how London's finest are wearing them.
HOW LONDON FASHION PEOPLE ARE WEARING CHUNKY CHELSEA BOOTS THIS WINTER
Style Notes: You can always count on Marianne to make easy combinations look polished, and we're taking notes on this maxi coat + jeans + boots combination.
Style Notes: Nothing says "autumn" quite like Monikh's chocolate-brown suede boots and shearling coat, but her bright Colville bag adds another layer of colour and texture that lifts the whole look.
Style Notes: Even head-to-toe black feels fresh when tucking leather leggings into an equally glossy pair of leather boots.
Style Notes: If you're still making the most of a mild autumn before the temperatures really drop, channel Mimi with bare legs and a micro mini. As soon as winter rolls around, just add a pair of black tights.
Style Notes: Given up on skinnies? Join the club. Lucy proves slouchy straight-leg jeans are a style in the most stylish influencers' wardrobes.
Style Notes: Francesca wears her The Row boots with simple yet chic jeans and a denim shirt that are perfect for weekend errand running.
SHOP THE BEST CHUNKY CHELSEA BOOTS
LOVE the monochrome and contrasting elastic on the ankle of these M&S boots.
The boots that inspired 1000 copies. The myth, the legend.
Or there's the brown suede for those who are good at keeping an eye on the weather to make sure they don't meet any rain. These look like they're selling fast!
Kurt Geiger isn't just sparkly heels and colourful bags. The brand is exceptionally good at everyday boots too.
I challenge you to find a better affordable option than Zara's chunky tread Chelsea boots.
A great sock-like elasticated ankle means you can streamline your look.
H&M never fails to impress us with its boot selection.
I've just discovered this brand which is new to Matches and the slightly higher ankle cut and sloping sole is a great new style.
Inspired by the aforementioned boots from The Row, these Arket boots have a furry lining for extra warmth, which is undeniably an essential this coming winter.
These khaki boots are a bit of something different. They're modern, sleek and perfect for every day.
There's nothing COS can't do right and these boots add to their list of great pieces.
A reliable pair of heavy-soled boots you'll want to wear for everything from a day at the office to a weekend dog walk.
Up Next: This Timeless Boot Style is Far From Boring—22 Pairs That Prove It
-
I've Mastered Hamptons Style—7 Outfit Formulas I Rely On Every SummerCoastal chic at its finest. No flight necessary.
-
Bad News, Sandals—Fashion Girls Are Already Wearing Their White Dresses With Autumn's Biggest Boot TrendI'll be following their lead.
-
8 Classic Outfits to Try This Summer If You're a French Girl at Heart (Like Me)Chic.
-
Stop With the Ankle Boots—Miniskirts Should Only Be Worn Like *This* in 2025Period.
-
Spotted in Los Angeles: The Coolest Shoes to Wear With Denim Shorts This SeasonDenim shorts never looked so good.
-
Is It Just Me, or Are Fashion People Everywhere Skipping Sandals for This Cooler Year-Round Silhouette?These boots were made for walking.
-
Summer Is Here! 4 Fun and Incredibly Chic Colour Combinations I've Spotted Fashion People WearingPerfect pairings.
-
I'm Heading to the South of France—15 Outfits I'm Re-Creating to Look Like a LocalEuro summer loading…
