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 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, oversize dresses, which she donned with the chunkiest trainers, Allen’s style 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 used to describe this shift when brought it up in the WhatsApp group I share with my school friends, to 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 practicality, and no pairing helps us do just that 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 ten frock styles, at least. This, however, doesn’t mean you need to select the most versatile sneaker 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 “dad” trainer trend (more on that in a moment) New Balance trainers have fast-become fashion’s go-to kick, 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.
The ideal summer layering piece.
Slip dresses get a playful update in ultra-bright hues.
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 “dad” trainers. What constitutes a dad gainer, 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 also comes in a sweet pastel colourway.
Don’t forget your crew socks!
Balenciaga elevates the dad-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 summer weddings and occasions.
Just add gold jewellery.
These look so much more expensive than they actually are.
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 summer.
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 summer dresses, just like Imani has done with her black cotton midi dress and purple-and-burgundy Nike trainer combination.
The ideal summer dress, I’d wear these everywhere, from picnics in the park to Aperols in the beer garden.
Such a sleek looking handbag.
These iconic kicks are selling fast.
Style Notes: If you’re a minimalist, then. chances are you’ll already have a pair of Superga’s timeless canvas trainers in your shoe collection. I love how Lauren has used hers to give her LBD a daytime spin.
Such a simple dress, but one that’s so effective on.
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 Michelle’s floral dress-and-running shoe combination?
I have my eye on this for an upcoming wedding.
This specific shade of Kelly green is trending hard right now.
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.
Staud arm-candy never fails to impress me.
These are currently sitting in my ASOS basket.
Style Notes: We’ve already established that monochrome trainers look chic with dresses, especially when you use them to contrast to a paler outfit, just like Kellie. As far as monochrome trainers go, they don’t come more classic than black and white Old Skool Vans.
Cropped 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.
Next Up: I Predict This Dress Trend Will Be Everywhere in a Months’ Time
