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One Woman’s Brave Search For The Perfect Skirt

In these dark days of winter, a dark skirt is your best bet.

By Rebecca Tay

Is there such a thing as the perfect skirt? Probably—but the thing with the perfect anything is that it so rarely feels perfect in the moment. In the moment, skirts often fail the practicality test: either they’re too tight, too short, too clingy, too sheer, or too trip hazard-y. And yet they continue to be the thing we turn to again and again. Indeed, finding the perfect winter skirt is like finding the perfect partner (but with more fabric involved).

That said, there are some pretty damn good skirts out there. For me, that means something that’s comfortable, easy to move in, and looks good with boots in the winter, sandals in the summer, and sneakers (both Vans and my new, very chunky, very Dad-like New Balance) all the time.

The ideal length varies: even in my late 30s, post-first child era, I’m not opposed to something above the knee—though calling that a mini is another debate altogether (in a word: no!), and only with something quite covered up and loose. Most of the time, though, my winter skirt mate of choice is dark and falls to the calf or ankle.


Skirt, Beare Park, $860 (similar here); Jumper, Oroton, $399; Shoes, Rebecca’s own (similar here) Necklace, Rebecca’s own (similar here).

As someone who was born and raised in Canada, double denim is in my fashion DNA, and there’s no keeping me away from a good denim skirt. This super dark, rinsed denim one by Diesel is probably best saved for days when I haven’t been to multiple birthday parties—both toddlers’ and 40ths. as it is svelte! A slim-line shape like this looks neat and tidy with an equally slim-line sweater; I love the bright tomato hue of this one by Ganni for really slapping you awake on cold winter days.

Now that we’re spending a little more time in the office again, this square skirt by Beare Park is a great pick if you’re after something a little more unique. I’ve long been a fan of the statement skirt (there were a few years when it felt like all I wore was sequinedprinted, and generally quite out-there skirts—and always with a thin grey sweater or a crisp, oversized white blouse), but this piece is actually very comfortable thanks to a bit of stretch, and it looks cool with just a simple cashmere crewneck. Avoid a blazer as the square panels do stick out on each side; opt instead for something you can tuck in and out of the way.


Denim skirt, Diesel, $166; Sweater, Ganni, $95 (similar here); Shoes, Ganni, $575.

This black Iris & Ink style, though, is probably more my usual jam. It has pockets (perfect for shoving snacks in for daycare pickup), and hits mid-calf, which some people swear is unflattering and hard to wear—but when you’re rocking boots and tights in the middle of winter, who the hell cares? It’s also black, and while I generally try and avoid wearing black up top, it’s obviously the most versatile shade there is.

So like the perfect partner, the perfect skirt may not really exist, and the hunt for it may be long and arduous—but finding the next closest thing is worth every stitch.

St. Agni






Iris & Ink


Iris & Ink


Photos by Michael Brunt

Styling by Bree Macara

Shopping Edit Lucy Wood


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BY Rebecca Tay

Rebecca is a fashion writer who has worked for NET-A-PORTER and Victoria Beckham. While her partner gets one foot of hanging space in their wardrobe, she has one whole section dedicated to just skirts.

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