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 dressminimidi or maxi—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 in the aftermath of lockdown, flat shoes continue to appeal, with swaths of new, chic and comfortable designs continuing to appear. If you're still getting used to leaving your heels at home, 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

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".

Cotton midis go with basically any shoes.

This sleek trainer style ties a casual outfit together.

Layer over a thick knit when the weather calls for it.

Every wardrobe needs a reliable pair of white trainers.

2. LITTLE BLACK DRESS + POINTED-TOE FLATS

Flat shoes to wear with dresses: Pointed-toe flats and a LBD

Photo:

@iamzoefoster

Style Notes: As we head towards party season, it's time to start honing our evening looks. Nothing says "it's time to dance" like a trusty LBD, but when you're wanting to be out all night, swap your platform heels for pointed-toe ballerinas for an elegant, elevated and supremely comfortable finish.

Style with or without white socks.

3. BILLOWY DRESS + SLEEK LOAFERS

Flat shoes to wear with dresses: Billowy dress and loafers

Photo:

@taffymsipa

Style Notes: As we move deeper into autumn, our trusty loafers have rightfully moved to centre stage in our wardrobes, working their way into all of our favourite outfits. Style the cold-weather favourite with a billowy cotton dress and plenty of layered knits as the weather continues to cool.

4. EVENING DRESS + STRAPPY MARY JANES

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.

Asymmetrical dresses are a growing trend for this season.