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 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.
Diane Kari wears a striped-intarsia knitted midi dress with colourful Adidas Gazelles.
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. Many of us are now keen to bridge the fashion gap between aesthetic and practical, and no pairing helps us do just that more than dresses with trainers. Combined, it's the perfect low-key summer look. However, it takes more consideration than you might think to curate. 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.
Taffy Msipa styles an ivory linen midi dress alongside her Salomon Xt-6 trainers.
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.
STYLISH TRAINERS TO WEAR WITH DRESSES THIS SEASON
1. RETRO
Style Notes: Tapping into the retro 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 summer. You’ll be hard-pressed to find a dress they won’t go with.
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A classic pattern in the perfect colour for summer.
A quilted bag will forever be timeless.
The trainers you’ll currently find on my wish list.
2. SPORTY
Style Notes: Trainers add a sporty spin to any minidress. It's the perfect way to make an outfit feel more casual throughout summer (you can dress it back up with heels later). What constitutes this style of trainer, I hear you ask? Usually a retro-style trainer with a thick-tread sole that you could easily walk 30,000 steps in. Just ask New Balance.
Shop the Look:
You can't properly pack for summer holidays if you don't have a white linen dress.
A neutral colour combo that goes with everything and is comfy to boot.
This style of sunnies has been trending for years — I'd argue it's a classic now.
3. MONOCHROME
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?
Shop the Look:
A dress you could wear to an array of occasions.
Just add a simple-yet-statement necklace.
Another comfortable pair that goes with everything.
4. HIGH TOPS
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.
Shop the Look:
This would also look cute with sandals, heels and ballet flats.
There’s no outfit that can’t be improved upon with a basket bag.
White Converse feel fresh for summer.
5. BRIGHT HUES
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? Imani has done just that with her black cotton midi dress and purple-and-burgundy Nike trainers.
Shop the Look:
This is the ideal LBD for warmer weather. I’d wear this everywhere from picnics in the park to dinner dates.
Colourful trainers are big news for 2024.
6. WHITE PLIMSOLES & SOCKS
Style Notes: If you’re a minimalist, chances are you’ll already have a pair of white canvas trainers in your shoe collection. I love how Maren has used hers to give her printed red dress a preppy spin.
Shop the Look:
For a gorgeous twist on a classic floral dress, get it in red.
I wear these all the time in the warmer months.
A blazer goes with everything, and it's ideal for cooler summer days.
7. RUNNER SHOES
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 Vivian's asymmetric dress-and-running shoe combination?
Shop the Look:
Summer dresses doesn't always have to mean florals and pastels, opt for a monochrome design instead and add trainers to make it feel more casual.
The ultimate leather cross-body bag.
These are currently sitting in my basket.
8. SKATER
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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Skater trainers look particularly good with floral minis.
DeMellier's handbags never fails to impress me.
Looking for a pair of white trainers? The destination is Nike's widely-loved Air Force 1s.
9. TONAL
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. Pairing it with other tonal neutrals like beige and caramel is a fun way to play with warm and cool colours.
Shop the Look:
Trench coats are timeless enough to last you year-on-year.
Strapless styles are everywhere at the minute.
Another chunky trainer to rely on in the warmer months.
This piece was published at an earlier date and has since been updated.
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