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.
1. NEW BALANCE
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.
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 Month’s Time