It’s Going to Be a Flat-Shoe Winter—These Pairs Are the Best of the Best

Up until about six years ago, aside from holiday sandals, I never used to wear flat shoes. Instead, I'd teeter around in heels, whatever the occasion—be it a night out or a trip to the supermarket. I guess I had subscribed to the idea that working in the fashion industry meant practical things such as flat shoes weren't part of the uniform. In my defence, flat shoes weren't given the same treatment that they are today.
Then the tide turned. From Céline's (when the brand still boasted its accent) Glove shoes to Gucci's once-again-iconic Jordaan loafers, the humble flat was given the haute treatment by a host of brands. Now, you'll find plentiful flat shoes that look just as pretty as heels, if not more so.
It's official—flat shoes are cool, and I wear them around the clock. Not only are they more comfortable than any of the shoes I wore during my early 20s, but I also trip less. (Note: It's imperative to pay attention when walking in five-inch stilettos and not get distracted looking at dogs.) And you know, I also feel much more stylish.
Ballet flats, loafers, Mary Janes—whatever your preferred flavour of flat footwear is, I've found the chicest pairs out there. Scroll below to see the best flat shoes on offer right now, from high-street, mid-range and luxury brands.
THE BEST HIGH-STREET FLAT SHOES
Jeanette demonstrates the trending way to wear loafers this season: with tall socks.
Shop High-Street Flats:
The colour is perfect for the coming winter days, and just think about cute they'll be for the festive season too!
One for those in-between seasonal days when it's not too cold.
Lovely with blue jeans and a trench.
THE BEST MID-RANGE FLAT SHOES
Marisa styles flat Mary Janes for the transitional period with a long dress and coat.
Shop Mid-Range Flats:
The benefit of Mary Janes is that the strap will stop your foot from slipping out.
The pointed toe on these would look great under tailored trousers.
Now to decide which cosy knit to style with these ballerina pumps...
The mock-croc finish sets these penny loafers apart.
Reformation's much-loved loafers come in a range of styles and prints.
THE BEST LUXURY FLAT SHOES
Marilyn opts for a modern monochrome look, teaming her Chanel ballet flats with balloon skirt and a black blazer.
Shop Luxury Flats:
The split toe may divide some people, but we love it.
Brunello Cucinelli makes the best classic shoes, case-in-point these bead embellished sued flats.
A party ballet flat if I ever saw one.
The tassels are the main part.
The sweetest ballet flat silhouette with a slightly sexy vibe.
I was sold the second I saw that pearl-embellished strap.
This post was originally published at an earlier time and has since been updated.
Maxine Eggenberger is Who What Wear UK’s Deputy Editor and has over fourteen years of experience in fashion journalism. She been creating engaging and authoritative content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, talent interviews self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their search and keyword planning, works closely with the fashion and beauty team on strategy and continues to pen many of her own articles. Prior to Who What Wear UK, Maxine's contributed to publications including Grazia, InStyle Marie Claire, Elle and Look, amongst others.
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