The 9 Pairs Of Flat Shoes To Bring Your Winter Dress Into 2026

If a dress feels too, well, dressy for this moment in time – totally understandable after the revelry of December– you can probably blame your footwear. I'm personally of the belief that heels, even the slightest block or Cuban, are simply too much for January. You need the grounding relief of a loafer, a brogue, a ballet pump, or, obviously, a sneaker, all of which, you'll be pleased to hear, go brilliantly with dresses.

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Yes, really, at the latest shows, frocks and flats got friendly, with multiple combinations to suit all dress personalities. If you're looking for something cool and cosy, Gabriela Hearst's sweater maxi plus slippers is the (only) way to go. For a high-romance formula, on the other hand, try a velvet dress and a criss-cross leather ghillie. Keep scrolling for the nine couples that made our list.

Knitted Dress & Textured Slippers

Gabriela Hearst's elongated sweater dress was matched in no-muss, no-fuss energy by slippers, the ultimate shoe if you want to ease, ever-so-gently, into 2026.

Velvet Dress & Ghillie Shoes

Sometimes your flats should contrast with your dress. At other times, however, you can lean into a single mood from top-to-toe, in this case a gothic kind of romance achieved with sloe-berry velvet and a modernised ghillie.

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Asceno Jody Dress Maroon Viscose Velvet

Lili Curia Isolde Ballet Sneaker

Coat Dress & Lace-Ups

If you want a throw-on-and-go kind of outfit, you could do a lot worse than a single-breasted coat that's a look all by itself. A bold colour is always a good idea – see cobalt at Jil Sander – which you can balance with a sturdy black lace-up.

Toteme Organic Cotton Trench Coat

Sessùn Astaire Derbies

Satin Dress & Ballet Pumps

This might sound like too saccharine a combination, but add ribbed knee-high socks – plus a coat that's casual in personality; an oversized funnel-neck, for example – and you've just found a way to maximise your party dress' cost-per-wear.

Arket Slouch Satin Dress

Massimo Dutti Crackled Leather Ballet Flats

Leather Dress & Square-Toed Shoes

A leather dress will provide more warmth than most other variations, especially if you layer it up with a quarter-zip knit, a shirt, a polo neck or a combination of all three. Match its means-business attitude with square-toed flats that will get you seamlessly from A to B.

Toteme Leather Tee Dress

H&M Mules

Printed Dress & Sneakerinas

Amp up the playfulness of a printed dress – whether it's a soft-focus ditsy or something more abstract – with a sneakerina, a seriously versatile flat that can be casual or 'out-out'.

Massimo Dutti Flowing Animal Print Dress

Puma Speedcat Go Shoes

Pinafore Dress & Leather boots

At Miu Miu, genius layering reached its zenith in this apron dress styled with slouched leather boots (as well as oodles of knitwear and silk). Channel the same vibe until summer when – hey presto! – you can lose everything bar the dress and boots.

Toast Patch Pocket Denim Dungaree Dress

YMC x Grenson Transmission Boots

Waistcoat Dress & Riding Boots

To begin the year with a (decided) boom, why not level up your workwear to a whip-smart waistcoat dress styled with leather riding boots? Easy to layer, and surprisingly comfortable, it's a uniform that can be styled multiple ways (over a ticker-striped shirt and wool trousers, for example).

Jigsaw Jigsaw V-Neck Waistcoat Dress Brown

COS Leather Knee-High Boots

Embellished Dress & Trainers

For an eveningwear option, look to Dries Van Noten, who sent an embellished black dress, complete with a fuss-free silhouette and pockets, down the catwalk with its signature footwear: sneakers.

Ghospell Augusta Embellished Midi Dress

Dries Van Noten Suede Sneakers

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