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.
Tagged: Trainers