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.
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.
Style Notes: Tapping into the sporty trainer trend (more on that in a moment), New Balance trainers have fast become fashion’s go-to kicks, with the brand’s more neutral styles selling out over and over again. Select a beige or ecru hue, and you’ll be hard-pressed to find a dress they won’t go with.
I’m obsessed with the thigh split.
Give your dresses a spring update with a knitted tank.
The trainers you’ll currently find on my wish list.
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.
This dress looks so much more expensive than it is.
Don’t forget your crew socks!
These elevate the sporty-trainer trend to chic new heights.
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?
A dress you could wear to an array of weddings and occasions.
Just add silver jewellery.
I can confirm these are very comfy and go with everything.
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.
This cult slip comes in so many prints.
There’s no outfit that can’t be improved upon with a basket bag.
White Converse feel fresh for spring.
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.
This is the ideal LBD. I’d wear this everywhere from picnics in the park to Aperols in the beer garden.
Such a sleek-looking handbag.
The original racer, modernise the colours and materials for 2023.
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.
There’s a reason these dresses always sell out.
My dream handbag.
I wear these all the time in the summer months.
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?
A long-sleeved dress is perfect for dress lovers in spring.
A stylised version of the running shoe.
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.
Such a cool print.
Patou’s arm candy never fails to impress me.
These are currently sitting in my basket.
Style Notes: We’ve already established that monochrome trainers look chic with dresses, especially when you use them to contrast a paler outfit, just like Kellie did. As far as monochrome trainers go, they don’t come more classic than black-and-white Old Skool Vans.
Oversized blazers are everywhere at the moment.
Use your trainers to give satin dresses a low-key spin.
Another trainer I personally rely on in the warmer months.
