9 Easy Dress-and-Trainer Outfits Fashion People Swear By

At the risk of showing my age, the first time I can recall someone wearing trainers with a dress (and doing it well) was when Lily Allen wore them in the video for her debut single, "Smile.” I was 16 at the time, and as I watched it on loop on the six or so music channels my TV got, I tried to comprehend that it had never occurred to me to wear the two together before. Twirling around in her tiered, oversized dresses, which she donned with the chunkiest trainers, Allen sparked a sartorial movement. Slipping into my first dress-and-shoe ensemble, I had never felt cooler. Pairing something deemed fancy with something so casual? It wasn’t just on-trend—it was freeing. Like we were tearing up a predetermined fashion "rule” and making up our own. Liberating was one word I used to describe this shift when I brought it up in the WhatsApp group I share with my school friends, with which everyone solemnly agreed. 

Fast-forward 16 years, and the dress-and-trainer look is still going strong. In fact, it’s never felt more relevant than it does now. Post-lockdown, many of us are keen to bridge the fashion gap between aesthetic and practical, and no pairing helps us do just that more than dresses with trainers. Curating such a look, however, takes more consideration than you might think. Out of the two, getting your trainers right is paramount over your dress. You need to be sure that your trainers work with the dresses you have in mind. Choose wisely, and you can easily style one pair with 10 frock styles, at least. This, however, doesn’t mean you need to select the most versatile sneakers on the market. With a little bit of know-how, even bold trainers can still be worn with a multitude of dresses if you get the balance right. 

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(Image credit: @champagnemani)

To help you unlock the best trainers to wear with dresses, I’ve curated a handy edit for you below, with outfits that help showcase their full potential. Scroll on, and you’ll be forgiven for never wanting to wear high heels with your dresses again. 

1.ADIDAS

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(Image credit: @nicoleocran

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Style Notes: Tapping into the sporty trainer trend (more on that in a moment),it's been a very good year for Adidas, and everything from the Samba to the Gazelle have fast become fashion’s go-to kicks, with the brand’s classic styles selling out over and over again. Select a black or ecru pair to wear with a neutral outfit, or a pop of colour that celebrates spring. You’ll be hard-pressed to find a dress they won’t go with. 

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2. SPORTY TRAINERS

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(Image credit: @raeannlangas)

Style Notes: Cute, floral, puff-sleeve dresses have been dominating the frock scene for the past few seasons. Give them a fresh overhaul that’s anything but saccharine with a pair of chunky trainers. What constitutes this style of trainer, I hear you ask? A usually white, retro-style trainer with a thick-tread sole that you could easily walk 30,000 steps in. Just ask New Balance. 

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3. MONOCHROME

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(Image credit: @chrissyford)

Style Notes: If you plan on wearing your trainers with printed dresses, you might want to consider looking for pared-back trainers that won’t detract from them. And what could be more classic than a monochrome pair? 

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4. CONVERSE

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(Image credit: @tamaramory)

Style Notes: Converse trainers have always been a go-to for fashion people, but right now, I’ve noticed more and more influencers are wearing them once again. If you've already invested in a pair, then kudos, for the high-top design is one of the easiest trainers to pair with dresses. 

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5. BRIGHT HUES

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(Image credit: @champagnemani)

Style Notes: If you prefer your shoes to do the talking, why not invest in a bold and bright pair of trainers to breathe new life into your basic spring/summer dresses? Imani has done just that with her black cotton midi dress and purple-and-burgundy Nike trainers. 

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6. SUPERGAS

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(Image credit: @kimturkington_)

Style Notes: If you’re a minimalist, chances are you’ll already have a pair of Superga’s timeless canvas trainers in your shoe collection. I love how Kim has used hers to give her floral mini a preppy spin. 

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7. RUNNER SHOES

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(Image credit: @styleidealist)

Style Notes: I’m no jogger, but I love to see those who run getting more wear out of their running shoes by styling them with things other than their leggings. How cool is Karina's shirt dress–and–running shoe combination? 

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8. NIKE AIR FORCE 1

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(Image credit: @claire_most)

Style Notes: I lived in skater trainers in my teens, and now Nike’s iconic Air Force 1 kicks are back, with fashion types wearing them with everything from wide-leg trousers to, yep, you guessed it, dresses. 

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9. GREY TRAINERS

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(Image credit: @kimturkington_)

Style Notes: We’ve already established that monochrome trainers look chic with dresses, especially when you use them to contrast a white dress outfit, just like Kim. As far as monochrome trainers go, they don’t come more contemporary than chic grey. It's the obvious choice for when black is too heavy, and white is too well, pristine. 

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Next Up: Spring/Summer 2023 Fashion Trends: 21 Expert Approved Looks You Need To Know About

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over twelve years of experience in fashion journalism. She been creating engaging and elevated style content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories, and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, works closely with influencer talent on content initiatives, represents the brand at industry events, and regularly contributes to social media. Previously, Maxine appeared on TV in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o. 


Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship, she was offered a position on the Look magazine fashion desk. She accepted, leaving university a year early in the process. She went on to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion writer along the way. She later served as Look’s acting Editor in Chief before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others. Maxine works remotely from her countryside home near Edinburgh.