Ava Gilchrist
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 style movement.
Singer Lily Allen wearing a dress and trainers look.
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. 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 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 statement 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.
9 Stylish Trainers to Wear With Dresses This Season
1. Monochrome
Style Notes: If you plan on wearing neutral-toned, classic trainer colour like white or grey, 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 outfit?
Shop the Look:
Knitted dresses are a perfect transeasonal staple that can be worn to any occasion. This one features a deep v-neck and is available in sizes XS to XL.
Gold jewellery always gives a look extra polish.
The suede tip and contrast three stripes are a classic that can seamlessly fit into your existing shoe rotation.
2. Chunky
Style Notes: From Hailey Bieber's beloved dad shoe-style New Balance 530 trainers to the more athletic Solomon styles taking over London suburbs like Stoke Newington to the runways of New York's Sandy Liang and New Zealand's Wynn Hamlyn, chunky trainers are back in a big way. When paired with a more delicate silhouette like a satin slip dress, these sneakers bring contrast and dimension.
Shop the Look:
Lean into romance with this puff sleeve dress from Dôen.
A simple way to elevate any dress-and-trainers outfit.
An intelligent styling hack we can always rely on is matching your trainers to a colour featured in your dress.
3. Performance
Style Notes: I lived in skater trainers in my teens, and now performance-based sneakers like the motocross-inspired Puma Speedcat and martial arts-style Adidas Taekwondo are making the rounds with fashion types wearing them with everything from wide-leg trousers to, yep, you guessed it, dresses.
Shop the Look:
Skater trainers look particularly good with floral minis.
Mango's sequin and lace slip dress is so elegant but pair it under a graphic t-shirt and performance-style trainers for a more everyday look.
Looking for a pair of trainers you can take from run club to after work drinks? Salomon's are your style.
4. Tonal
Style Notes: We’ve already established that monochrome trainers look chic with dresses, especially when you use them to enhance a classic white dress outfit. As far as monochrome trainers go, they don’t come more contemporary than ecru tones. 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, black and ivory is a fun way to play with warm and cool colours.
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There's something so classic about a shirt dress. This midi-length version features a tighter fit and is available from size 4 through to 26.
A chic carry all that works with casual outfits.
Adidas's Japan trainer is a sleek alternative to the Sambas, featuring a tumbled leather finish and contrasting suede stripes.
5. Retro
Style Notes: Tapping into the retro trainer trend is a simple way to invest in a 'new' sneaker. Not only will there be plenty of styling inspiration available, but you'll know that they'll be able to worn for years to come. You’ll be hard-pressed to find a dress they won’t go with.
Shop the Look:
Take cues from '80s fashion and pair your retro sneakers with a denim jacket.
The perfect one-and-done piece.
The classic canvas Superga style is the ultimate retro sneaker.
6. 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 this Y2K asymmetric dress-and-running shoe combination?
Shop the Look:
If handkerchief hems aren't for you, try something different with this off-the-shoulder draping.
COS is our one-stop shop for leather cross-body bags.
This pink and brow colour combination is an elite pairing.
7. Clashing 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 dresses? Salomon and Puma are brands that both offer trainers in super saturated colours, as Emily Ratajkowski has shown us time and time again. I especially like them when they're used to clash with an equally bright dress.
Shop the Look:
A scoop neck dress is a wardrobe classic, and this ombré version from B-Corp fashion brand, Faithfull The Brand, brings such a luxurious twist to a French Girl classic.
Put an opulent twist on the classic market bag with this woven burgundy leather iteration from St. Agni.
These bright trainers are Bella Hadid-approved.
8. Bright
Style Notes: If you want to instil your look with some colour, but aren't quite ready to clash your kicks like the above, try adding a bright trainer to a classic white dress.
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This would also look cute with sandals, heels and ballet flats.
There’s no outfit that can’t be improved upon with a raffia bag.
Adidas Gazelles combine some of the biggest trainer trends—namely, sporty and colour block.
9. Sporty
Style Notes: Trainers add a sporty spin to any minidress. It's the perfect way to make an outfit feel more casual throughout the warmer months (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:
A minidress that will work on all of your warm-weather holidays this year.
This style of sunnies has been trending for years — I'd argue it's a classic now.
A neutral colour combo that goes with everything and is comfy to boot.
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