How to wear high top Converse—ageless, expert-approved styling tricks and tips

Everything you need to know about how to wear high top Converse to help you get the most of this wardrobe staple.

street style influencers demonstrating how to wear high top converse
(Image credit: Getty)

The question of how to wear high top Converse—AKA Chuck Taylors—is one that continues to crop up, because of all our trainers, Converse is a brand that we come back to time and time again. 

Converse high tops are the smart addition to a capsule wardrobe. They’re relatively inexpensive (you can pick up a pair for around $60 or £57), incredibly versatile (complimenting your best jeans just as well as they do summer dresses), and only look better the more scuffs they accumulate. They won’t date either, especially if you go for a classic colorway like black and white. No wonder celebrities including Julia Roberts and Jessica Alba are fans. 

“Converse are an easy-to-wear piece that works whatever your personal style,” says style consultant Charlotte Verdeyen. “They go with every type of outfit; from grounding a bright or patterned look to dressing down a satin slip dress. As a stylist, I encourage all the ladies I see from 20 to 60+, to invest in a pair.”

“They're really an all-time classic trainer and exceptionally comfortable,” adds Rachel Ingram, Editor in Chief at Threads Styling. “I've had a pair for over 10 years now and still love them.” 

Originally launched as a basketball trainer back in 1917, Converse’s iconic Chuck Taylor All Stars have been imagined in countless colorways over the years. The brand has collaborated with a number of designer labels too, the most notable being the Japanese fashion label Comme des Garçons. Despite this, the fundamental details have remained almost exactly the same—canvas fabric, a single stripe at the side of the wide sole, and Chuck Taylor patch at the ankle.

How to wear high top Converse

Despite them being a bonafide style classic though, they're not always easy to style. We break down how to wear Converse high tops well, whatever your outfit preference, age and signature style. 

How to wear high top Converse with dresses

street style influencers showing how to wear high top Converse with dresses

(Image credit: Getty)

Sleeker than Stan Smiths or Vans and edgier than pumps or sandals, high top Converse will give even your frothiest, most feminine dresses an edge. “Converse are a great addition to dresses, making your outfit feel slightly less girly,” says Ella-Louise Gaskell, celebrity stylist and founder of P.S. Online Styling. “They’re both casual and cool.”

“High top Converse have a flattering slim fit so look great with oversized floaty dresses,” continues Rachel Ingram. Good news, especially given that smock dresses are a huge clothing trend for 2021. 

Bright Converse are a lovely way to add vibrancy and personality to an otherwise simple or monochrome outfit, or to create a playful color clash when wearing block-color dresses. If you’d prefer something more understated, black or white high tops will go with pretty much any dress in your closet. A midi or maxi length will reveal just a flash of your shoes, while a mini will really show them off. 

How to wear high top Converse with jeans

street style influencers showing how to wear high top Converse with jeans

(Image credit: Getty)

“High top Converse are great because they go with literally any type of jean,” says Ella-Louise Gaskell. “My favourite way to wear them is with boyfriend style straight-leg jeans, as these tend to come with a raw edge (meaning it's slightly jagged and not hemmed). The combination of the straight cut and high tops elongates the legs too.”

If your jeans are wide, straight or mom shaped, you’ll be able to layer them over your Converse with ease, if they’re skinny jeans, you may need to tuck them into your shoes. 

As for styling your top half, the world is your sartorial oyster. “I would style high top Converse and jeans with a band or slogan tee and leather jacket. Or a textured oversized blazer and statement necklace,” says Charlotte Verdeyen. “I also love wearing the same jeans with a silk oversized sleeveless blouse and black tuxedo blazer.”

How to wear high top Converse during summer

street style influencers showing how to wear high top Converse during summer

(Image credit: Getty)

“High top Converse look great in the summer and will give your look a bit of a grungy edge,” says Deputy Fashion Editor Charlie Bell. “Ideal for wearing in a busy city—or when you're not quite pedi-ready for sandals—Converse pretty much work with everything from strappy dresses to denim shorts.” They’re especially good for in-between days, when the weather can’t quite make up its mind. Or, when you know you’ll be doing lots of walking. 

“For versatility, I like the high-top Converse in black. The canvas fabric makes them hot-weather appropriate while the higher cut gives them a black ankle boot effect that is easy to style with skirts and trousers. Wear with a color-popping suit for a casual spin that you can rock during the day or dress down your slinky evening slip dress with some cool Converse and a denim jacket.” Low cut trainer socks will go undetected, or choose a pair in a contrasting color, or with detailing around the hem, to add extra interest. 

How to wear high top Converse during winter

street style influencers showing how to wear high top Converse during winter

(Image credit: Getty)

“Look no further than high top Converse in winter for casual footwear that keeps you covered,” says Style Editor Joely Chilcott. “When a boot feels too heavy and normal trainers with jeans leave that slither of bare ankle left open to the elements, the high top reigns supreme.”

The options for how to wear high top Converse in winter are endless. Layer beneath jeans, tapered trousers or wide-leg leather culottes and team with a roll neck jumper to give your everyday outfits a retro feel. A padded puffer or chic wool blend coat is the perfect finishing touch. High top Converse work just as well with dresses during cold spells too, whether your poison is a floaty floral midi with long-sleeves or a chunky knitted dress. A pair of high denier black tights will both protect your legs from the chill, and negate the need to wear socks. Just watch out for puddles or you'll find out the hard way that these shoes aren't waterproof.

Best high top Converse to shop now 

Jess Beech

Jess Beech is an experienced fashion and beauty editor, with more than eight years experience in the publishing industry. She has written for woman&home, GoodtoKnow, Now, Woman, Woman’s Weekly, Woman’s Own and Chat, and is currently Deputy Fashion & Beauty Editor at Future PLC. 

She caught the magazine bug during a stint as Fashion Editor of her university newspaper alongside her English degree, and hasn’t looked back since. As for the fashion bug, that came as part and parcel of growing up in the 90s, but the less said about that the better!

Jess’ average day in the office is spent researching the latest fashion trends, chatting to industry tastemakers and scouring the internet to bring you this season’s must-buy pieces - as well as advice on how to wear them. Weekends are equally fashion-focused, and Jess has been known to visit no less than five Zara stores in a single day in search of the perfect occasion dress. 

The only thing that comes close to a buzz of finally tracking down that much-coveted dress is the joy of discovering a new beauty wonder product or hero ingredient. A beauty obsessive, Jess has tried everything from cryotherapy to chemical peels (minus the Samantha in Sex and The City-worthy redness) and interviewed experts including Jo Malone and Trinny Woodall.