How to Wear High Top Converse With a Dress
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
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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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H&M Raglan-Sleeved Dress
RRP: $34.99 / £24.99 | This oversized dress is the perfect summer throw-on-and-go frock and ideal for brunch outfit ideas. There's a belt for added structure and the voluminous sleeves add extra drama.
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Nobody's Child Eve Midi Dress
RRP: £69 (International shipping available) | Or why not try this picnic print perfect dress. One of the best green dresses this season, it has a fitted bodice and a flared skirt for ease of movement and a stylish tieback finish.
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Converse Chuck Taylor All Star
RRP: $65 / £60 | The OG of Converse high tops - white Chuck Taylors, guaranteed to go with any outfit thrown at it, you'll get endless wear out of these. Keep them fresh with our handy guide on how to clean white shoes.
2. How to wear high top Converse with jeans
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"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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Cos Tapered-Leg High Rise Jeans
RRP: $120 / £69 | These tapered high rise jeans are oh-so-flattering and the perfect companion to your high tops. They're sustainably crafted from non-stretch organic cotton too. Roll up the hem for a great answer to how to wear high top Converse.
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All Saints Fern Leather Biker Jacket
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Converse Chuck 70 Vintage Canvas
RRP: $85 / £85 | A pair of black high tops offers just as much versatility as a pair of black ankle boots or your best Chelsea boots during the winter months. These have been given an upgrade with premium canvas and a sleek vintage aesthetic.
3. HOW TO WEAR HIGH TOP CONVERSE WITH A SUIT
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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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Whistles Bella Pleat Front Trousers
RRP: $239 / £119 | One of the top fashion color trends 2022, these lime trousers are sure to get you noticed. With a leg-lengthening, wide leg cut, your Converse will just peep out the bottom of your trouser leg. Team with fresh whites.
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Whistles Crepe Boyfriend Blazer
RRP: $299 / £149 | This blazer has a borrowed-from-the-boys look for a relaxed finish. Layer over the matching pants, or add polish to your best midi dresses for a smart and versatile way of how to style a blazer. Making this an easy, staple cover-up.
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Converse Chuck 70 Canvas in Pink
RRP: $85 / £80 | For a color clashing look, team a vibrant suit with some contrasting Converse. Pink and green make for one dreamy color combo, these have all the classic features from the ankle patch to the comfy insole with added brightness.
4. HOW TO WEAR HIGH TOP CONVERSE WITH AN ALL-IN-ONE
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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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Lucy & Yak Ragan Jumpsuit in Yellow
RRP: $73 / £58 | One of the best sustainable clothing brands, Lucy & Yak's jumpsuits are great for your wardrobe and the planet. This has a zip fastening making it easy to get on and off and non-stretch fabric in an A-line shape for a figure flattering finish.
Baukjen Organic Stretch Dungarees
RRP: £96 (International shipping available) | Dungarees can be grown-up, and we love this sleek khaki design. Boasting a relaxed fit, layer over a plain or striped tee and swap for a roll neck when it gets cooler. The adjustable straps will help with the fit.
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Converse Chuck 70 Crafted Stripe
RRP: $85 / £85 | Up the ante on your classic Converse with this sleek striped design. The blue and white combo keeps them timeless and easy to pair with anything from denim to dresses. As an added bonus, they're made from partly recycled materials.
5. How to wear high top Converse during 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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Arket Non-Stretch Denim Shorts
RRP: $59 / £45 | Denim shorts paired with high tops will have you field-ready if you're wondering what to wear to a festival this summer. These have a relaxed fit and sit high on the waist before flaring out for a relaxed finish across your thigh.
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Free People Oh So Low Midi Skirt
RRP: $88 / £78 | Or why not try Converse with a feminine slip skirt to give your look a rock 'n' roll edge, making it appropriate for daywear or less dressy events. We love the deep teal hue but you can also snap it up in pink and lime green too.
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Converse Chuck 70 Crafted Patchwork
RRP: $90 / £95 | If you're opting for a more lowkey outfit then a pair of printed Converse will help elevate your look. We love this patchwork print delivering a bohemian, '70s vibe - ideal for teaming with denim of all hues and pretty white flowy frocks.
6. How to wear high top Converse during Fall
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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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& Other Stories Half-Zip Sweater in Stripes
RRP: $129 / £95 | When a Breton top doesn't quite cut it during a cold spell, enter the striped knit. The half-zip sweater was a huge hit last fall and we predict it'll be a sell-out again this year.
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M&S Leather Ankle Grazer Trousers
RRP: $315 / £179 | Just as versatile as jeans but cooler, it's time to learn how to style leather pants. These have an elasticated waist and straight leg for that jogger-feel with a smarter finish.
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Converse Chuck Taylor All Star Lift Platform
RRP: $75 / £85 | Add some subtle height with a pair of platform sneakers. The gold detailing on this pair adds a touch of subtle glamour and the gold eyelets help to add a fancy finish too.
Source: https://www.womanandhome.com/us/fashion/how-to-wear-high-top-converse/
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