6 Winter Outfits That Look So Much Chicer With Flat Shoes

Flats have been the dominant footwear choice of 2023, period. From ballerinas to Mary Janes, loafers to clogs, fashion people everywhere are forgoing stilettos in favour of comfortable (but no less stylish) flat shoes. And we predict this infatuation will last well into 2024, too.

But as we adjust to lower temperatures, the question on every flat-shoe fan's mind is, "Can this trend be adapted for the winter months?” The answer, I'm pleased to share, is yes—but with an asterisk. It's natural for boots to feel like the only safe option if you struggle with cold toes at this time of year, and this might well be the case for some, but we've seen first-hand how influencers have made daintier shoes work in chilly weather.

The below outfits are prime examples. As they suggest, long trousers, insulating coats and wool knitwear are key to ensuring you're cosy top-to-toe. From there, you can add socks or sheer tights to retain the heat in your feet. Simple.

At the first sign of snow or minus degrees, you might want to rethink some of these looks, but until then, get inspired by our round-up of the best winter flat shoe outfits.

1. Scarf Coat + Indigo Jeans + Mary Janes


(Image credit: @modestmira_)

Style Notes: Scarf coat season is here—it's time to bust out your Toteme beauty, or finally give into the temptation. There are also great alternatives on the high street that will look just as chic with this jeans-and-Mary-Janes combo.

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2. Camel Coat + Tailored Trousers + Ballet Flats


(Image credit: @anoukyve)

Style Notes: This is an outfit I can see myself wearing on repeat. It's a simple but foolproof formula: take any long coat, pair it with tailored trousers, flats and a wool knit for added warmth.

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3. Blazer + Leather Trousers + Loafers


(Image credit: @astyleedit)

Style Notes: Loafers are a footwear staple at this time of year, and they're easy to incorporate into a whole range of looks. I love Lauren's monochrome styling here. We've said it before and we'll say it again: there are few outfits a blazer won't make better.

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4. Grey Coat + Turtleneck + Socks and Loafers


(Image credit: @nnennaecham)

Style Notes: If you've decided to brave bare legs, it might be wise to pair your loafers with socks, like Nnenna. A cosy knit and longline coat are also essential to keeping this outfit cold weather-appropriate.

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5. Wool Coat + Wide-Leg Trousers + Clogs


(Image credit: @francescasaffari)

Style Notes: It being December, Birkenstock sandals have cleared the way for the more winter-friendly Boston clogs. I always look to Francesca for tips on how to style them—this is an ensemble you can likely re-create using pieces you already own.

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6. Tweed Jacket + Baggy Jeans + Pointed Flats


(Image credit: @lindseyholland_)

Style Notes: On milder days, opt for a lighter-weight tweed jacket (a Parisian favourite) and give it some edge with wide-leg jeans. A pair of pointed flats will look super sleek peaking out from the bottom.

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Next Up: 7 Anti-Trend Outfits People in London, Paris and Stockholm Are Wearing Right Now

Freelance Fashion Editor

Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at print and digital publications in Berlin and London, including Dazed & Confused and Indie magazine.

A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.

In her spare time, Bébhinn enjoys perusing Edinburgh’s best vintage shops, working through her out-of-control book collection and watching dog reels on Instagram.