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

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. “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.
2. HOW TO WEAR HIGH TOP CONVERSE WITH JEANS

“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.” Read More...