Take a Break From Your Jeans—Try These 8 Chic Skirt Outfits Instead

From the outset, you might find deciphering how to wear a skirt during winter a little tricky. Sure, they don't have the same throw-on appeal as dresses, and they might not be as simple to slip on with any top as jeans are, but with a bit of know-how, I'm here to help you unlock their true potential in the colder months. Taking time to perfect a handful of winter skirt outfits will significantly up your style game for the season ahead and will stop you from growing tired of your aforementioned dresses and jeans. Sound good? Let's get to it.

The beauty of wearing skirts in winter is that there are literally hundreds of skirt variations to choose from—and just as many ways to style them. Personally, I don't tend to wear miniskirts in summer, as my legs aren't my favourite thing to highlight (but hey, that's just me—more power to you if you're the opposite). But in winter, there's nothing I love more than slipping on a cute pleated mini or a checked pelmet with a pair of fresh, velvety opaque tights (more on that later). Then there are slip skirts, which, after making a monumental comeback four years ago, look even more premium come winter when fashion types wear them with their most luxurious knitwear and boots.

I could talk about the styling potential of skirts all day long, but perhaps a better use of my time would be to show you some of my favourite winter skirt outfits to inspire your own looks. Scroll on to see the eight I've hand-picked and to shop any pieces you might need to re-create them should you not already own them. 


Winter Skirt Outfits: @_jessicaskye wears a slip skirt in winter



Style Notes: As we already mentioned, slip skirts came back on the fashion scene four(ish) years ago and have been going strong ever since. Come winter, everyone loves to pair theirs with oversized knitwear. If you’re going to a party, switch out your shoes in favour of a pair of strappy sandals like Jessica Skye's. 

Winter Skirt Outfits: @shhtephs wears a pleated midi skirt with a check shacket



Style Notes: Pleated skirts are considered by many to be a classic item, which is why they pair so well with more trend-led pieces. Take Stephanie Arant; she’s styled hers with a bold checked shirt, which looks all the more polished thanks to her timeless skirt choice. 


Style Notes: Chances are you’ve owned at least one leather miniskirt in your lifetime, be it real or faux. If you still have one lurking in your wardrobe, you’ll be pleased to hear they’re set to be a big trend this winter—a ripple effect of the miniskirts that dominated the runways. Pair yours with a statement knit and shirt like Oluwaseun did, and you’ve got a look that’ll see you through just about every winter outing. 


Winter Skirt Outfits: @thandimaq wears a knitted jumper and skirt set



Style Notes: You’ll be hard-pressed to find anything chicer than a knitted skirt-and-jumper set. Be it high-end or high-street, they always look expensive—particularly when paired with leather knee-high boots, as Thandi Maq proves. 

Style Notes: A recurring look I keep seeing this season is influencers clashing their checks—a trend that was born on the runways of Dior and Longchamp. And one of the easiest ways to channel it is by way of a skirt, just like Jessica Torres has done with her zip-front mini and her shacket. 


Style Notes: When it comes to styling new outfits, one of the biggest hurdles can be getting your colours right. So let’s remove it from the situation. Monochromatic outfits were all over the runways and are anything but boring. Case in point: Imani Randolph’s white miniskirt and black jumper. 


Winter Skirt Outfits: @monikh wears a tulle skirt with a fuzzy jumper



If the last two years have taught us anything, it’s that we needn’t save our best pieces for best. Instead, you should show your fancy pieces year-round love by styling them with neutralising basics. Take your cues from Monikh Dale, and try wearing a pretty skirt—hers is tulle!—with a cozy knit.

Style Notes: If you’re anything like me, you’ll find inordinate amounts of joy slipping on a never-before-worn pair of tights. This season, playful printed hosiery is in. Ease yourself in with a pair of polka-dot tights. For a subtle print clash, try wearing them with a printed skirt, like Lucy Williams did.

Related Stories