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.

a composite of street style influencers showing 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. While they might fall into the sneaker category, because of the ankle-hugging high top, they can leave many in quite a style spin.

Converse high tops are a smart addition to any capsule wardrobe. Relatively inexpensive (you can pick up a pair for around $60 or £57), they're incredibly versatile - working with everything from jeans to dresses - and look great box fresh or well-loved. 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. 

Originally launched as a basketball trainer back in 1917, Converse’s iconic Chuck Taylor All Stars have been reimagined in countless colorways over the years. 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. But despite their iconic status, the slim ankle fit can leave many wondering how wear high top Converse, as they do differ to regular trainers.

How to wear high top Converse

If you're struggling with how to style high top Converse - confused by their almost boot-like silhouette, don't just take our word for it when we say they go with absolutely everything.

“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.” 

Here's how to wear high top Converse with every type of look, according to fashion experts...

1. How to wear high top Converse with dresses

a composite of street style influencers showing how to wear high top converse with dresses

(Image credit: Getty)

Sleeker than your best white trainers - think Stan Smiths or Vans, and edgier than pumps or your best sandals, high top Converse are the comfortable flats that will give even your frothiest, most feminine dresses a sporty 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 (opens in new tab). “They’re both casual and cool.”

“High top Converse have a flattering slim fit so look great with oversized floaty dresses,” continues Rachel. Good news, especially given that smock dresses are a huge fall 2022 fashion trend.

Bright Converse trainers are a lovely way to add vibrancy and personality to an otherwise simple or monochrome outfit - hello dopamine dressing - 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. 

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2. How to wear high top Converse with jeans

a composite of 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. “My favorite 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 you're trying to work out how to style flared jeans, or you've opted for a straight or mom shape, 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. “I also love wearing the same jeans with a silk oversized sleeveless blouse and black tuxedo blazer.”

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3. HOW TO WEAR HIGH TOP CONVERSE WITH A SUIT

a composite of street style influencers showing how to wear high top Converse with a suit

(Image credit: Getty)

The best Converse trainers have the ability to ground any look, instantly giving your outfit an effortless vibe and nailing that smart-casual aesthetic. Suits and coords are no longer reserved for the boardroom so if you want to give tailoring a casual spin at the weekend, team with your favourite Converse.

“If we’ve learnt anything from the past two years, it’s that comfort is key and wearing Converse with a tailored two-piece is a perfect high-low mix that’s comfortable and empowering,” says Paula Moore, fashion director at woman&home.

Weave in other casual elements to your look to keep it balanced, such as layering your blazer over your best t-shirt or slip on a baseball cap for a sporty twist. Colorful suits keep the look playful and directional or you can keep it tonal and team a camel suit with neutral colored Converse for a sleeker vibe.

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4. HOW TO WEAR HIGH TOP CONVERSE WITH AN ALL-IN-ONE

a composite of influencers showing how to wear high top converse with a jumpsuit

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Much like your favorite denim, styling Converse with a flattering jumpsuit is an easy off-duty look to master. “People are often afraid of jumpsuits and boilersuits because they think they are hard to style but in reality they are incredibly easy to wear. In fact, just like a midi dress, an all-in-one is a ready made outfit that requires minimal styling - just a few accessories and you’re good to go,” says Paula.

“I love teaming my high tops with a boilersuit for a cool utilitarian feel. Stay classic in a khaki romper and white Converse or mix it up in vibrant colors head-to-toe, choose whatever suits you and your style.”

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5. How to wear high top Converse during summer

a composite of street style influencers showing how to wear converse in the summer

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“High top Converse look great in the summer and will give your look a bit of a grungy edge,” says Paula. “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 a 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. 

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6. How to wear high top Converse during Fall

a composite of street style influencers showing how to wear high top Converse in the winter

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“Look no further than high top Converse in fall for casual footwear that keeps you covered,” says Paula. “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 fall are endless. Layer beneath jeans, tapered trousers or wide-leg leather culottes and team with your best sweater 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 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.

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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 a former Deputy Fashion & Beauty Editor at Future PLC. 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.

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