FASHION
5 WAYS TO WEAR CHELSEA BOOTS THIS SEASON
By Ayis Stephen-Diver, 1 September 2025
Picture: Getty
Chelsea boots are a wardrobe staple – trend cycles come and go but these stompers will never fall out of favour. Each season we see different interpretations on the runway, from sleek and slimline styles to knee-highs and ones with soles so chunky we're not sure how the models even pick up their feet. But one thing remains – the Chelsea boot's enduring style. We're here to tell you why they're such a versatile staple and how we'll be wearing them for AW25.
WHAT'S THE HISTORY OF THE CHELSEA BOOT?
They’re the brainchild of Queen Victoria’s shoemaker Joseph Sparkes-Hall, who designed them for her comfort and horse riding. A century and some Cuban heel-modifications later, they were adopted by the Mod scene – becoming the unofficial boot of The Beatles and the Chelsea neighbourhood, which they're named after, of course.
Picture: Getty
WHAT IS A CHELSEA BOOT?
Defined by an ankle-hugging fit, low heel and elasticated side panels, Chelsea boots are among the most popular shoes in the world. And for good reason – they blend practicality, comfort and style in a way every aesthetic and subculture can appreciate. Despite some changes over time, Chelsea boots have maintained one key characteristic that sets them apart from other ankle boots: their slip-on capability. Chelsea boots always have two panels of elastic on either side and a pull tab for easy wear.
The rest is entirely up to you: pick from lug soles or classic rubber soles, low heels or Cuban heels, suede or leather designs. The beauty of Chelsea boots is that there’s a pair for every situation. And to prove it, we asked ASOS' Styling Manager, Will Johns, for his take: 'Chelsea boots are a versatile winter essential, perfect for grounding an outfit’. And we're going to show you how to style Chelsea boots to do just that.
#1: CHELSEA BOOTS WITH JEANS
Pictures: ASOS
When it comes to the classic combo of boots and denim, take your styling advice from Will: 'Contrast black boots with cream jeans, or pair them with heavyweight indigo denim for a chic, premium feel. For a sharper silhouette, go with a straight cut jean or looser style that puddles at the ankle for an effortless look'. Indigo denim is everywhere this season, and its elevated look deserves an equally elevated boot choice. Go for a more angular pair that'll elongate the legs, and team it with classic silhouettes like a trench coat or a blazer.
GET THE LOOK:
ARRANGE two tone lapel double breasted trench coat in tan, £200
Topshop everyday tee in white, £10
#2: CHELSEA BOOTS WITH T-SHIRTS
Picture: ASOS
Pictures: ASOS
If you’re a fan of 2010s trends, you can already visualise the fashion blogger uniform of tees half-tucked into denim shorts and grounded with Chelsea boots (90210's Ivy says hello). Cringe not, because this look is back on social media’s radar – just substitute the denim shorts for jeans to beat the cold weather. If you want to pay homage to Chelsea boots’ rock 'n' roll heritage, there’s nothing like a band tee. To capture the aesthetic, look for a graphic T-shirt in charcoal grey, opt for acid wash or grey denim and team everything with studded accessories and a distressed leather jacket.
GET THE LOOK:
Dr Martens Maybole chelsea boots in burgundy leather, £190
ASOS DESIGN Oversized T-shirt with band graphic in washed charcoal, £22
Noisy May Brandy mid rise loose fit jeans in washed black, £32
ASOS DESIGN vintage wash leather look bomber jacket in washed black, £60
#3: CHELSEA BOOTS WITH DRESSES
Pictures: ASOS
If you thought Chelsea boots were too utilitarian to be worn with dresses, think again. ‘Play with textures for a cooler high-low look – use the boots to toughen up softer dresses and skirts,' says Will. Breaking up a casual mini dress – choose one in a trending polka-dot print for AW25– with Chelsea boots adds a bit of edge to the traditionally feminine silhouette. Add tights or socks that peek out for extra style points, and don’t sleep on satin dresses either – pair them with studded Chelsea boots and silver hardware for a grunged-up evening look.
GET THE LOOK:
ASOS DESIGN Wide Fit Rae chunky heeled chelsea boots in black, £42
Nobody's Child Petite Lyndsey ruffle detail mini dress in black spot, £59
Topshop faux suede patch pocket boxy jacket in brown, £76
Topshop Scarlett real leather suede shoulder bag with contrast strap in black and chocolate, £65
#4: CHELSEA BOOTS WITH BASICS
Picture: ASOS
Pictures: ASOS
Want a break from your 9-5 rotation of loafers and ballet flats? All those corporate-ready and back-to-school-friendly styles like cardigans, knitted vests and smart trousers are just as effective with some Chelsea boots on – and they adhere to the dress code, too. Black Chelsea boots are your best bet, and you can go even bolder with knee-high Chelsea boots to shield your shins from the cold. A real power move is wearing a full suit or tailored separates with Chelsea boots – ideally ones with higher heels for an elevated feel.
GET THE LOOK:
Similar: Walk London Dana tall chelsea boot in brown leather, £120
ASOS DESIGN wool blend pinstripe formal blazer in navy, £75
ASOS DESIGN wrap button and pocket detail mini skirt in grey, £30
Topshop knitted ribbed button crew cardigan in red, £36
Princess Polly Zifa fitted collared shirt in blue, £42
#5: HOW TO DRESS UP CHELSEA BOOTS
Pictures: ASOS
We’ve covered day-to-day Chelsea boot outfits, but what about for evening? First things first, choose a polished pair with your preferred heel height. Outfit-wise, let double denim, leather skirts and floor-sweeping faux-fur coats make up your AW25 night-out capsule. And then accessorise to the max – think a statement clutch and chunky jewellery.
GET THE LOOK:
Topshop Nisha block heeled chelsea boots in burgundy, £48
Topshop faux fur collarless long coat in natural stripe in beige, £130
Mango 100% cotton straight jean co-ord in indigo, £49.99
Similar: Topshop Ginny metal handle grab bag in khaki, £28
