Some Flat-Shoe-and-Dress Combinations Don't Work, But These 4 Definitely Do

Once upon a time, it was almost inconceivable to imagine styling a dress with anything but heels. Whether heading into the office, going out for lunch on the weekend or attending a special event, our poor feet never got a break. But luckily for both our wardrobes and our ankles, times have changed and trends have evolved. These days, we're styling almost any dress in our wardrobe with flats of some sort, whether that be sleek trainers, pointed-toe ballet flats, or pair of sharp loafers.

All of these covetable styles will evoke a different mood in a dress, depending on which you choose; and it certainly helps that flat shoes continue to be a top footwear trend for 2024, with swaths of new, chic and comfortable designs continuing to appear. If you're still trying to figure out how to swap out the heels for flats this season, read on top discover four ways to wear flat shoes with dresses that are easy to copy, along with my shoppable picks for re-creating the look.

1. MIDI DRESS + RETRO TRAINERS

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(Image credit: @stylewithsoco)

Style Notes: Unlike chunky trainers, sleeker retro styles add a cool edge without dressing down a dress too much. Adding a grounding element to a flowy midi, the charm of retro trainers is in their sporty edge that can make any pretty dress feel more "fashion".

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2. LITTLE BLACK DRESS + POINTED-TOE FLATS

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(Image credit: @iamzoefoster)

Style Notes: A trusty LBD is a wardrobe must-have, especially for evening events. A pointed-toe flat allows you to keep the outfit polished without punishing your feet with an uncomfortable stiletto.

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3. BILLOWY DRESS + SLEEK LOAFERS

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(Image credit: @taffymsipa)

Style Notes: As we approach warmer days, a billowy dress becomes more and more tempting. But to keep it professional enough for work—and suitable for unpredictable British spring weather—a trusty loafer is in order.

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4. EVENING DRESS + STRAPPY MARY JANES

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(Image credit: @borislavasekova)

Style Notes: Gone are the days when we had to bring out the heels when dressing for an occasion. Strappy Mary Janes make for an elegant pairing that will see you through your evening events in style.

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This piece was originally published at an earlier date and has since been updated.

News Writer

Natalie Munro is Who What Wear UK’s news writer. Previously freelance commerce writer at British Vogue, Natalie’s experience spans journalistic and styling roles, which have seen her work on shoots for publications such as British Vogue, Vogue Ukraine, AnOther Magazine and Elle UK and write for publications including British Vogue and Conde Nast Traveller. With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news and trends for Who What Wear UK, with a particular focus on celebrity style and emerging fashion trends.