Winter is often considered the most difficult season to dress for. In summer you can throw any old dress on and look put-together, but in winter there’s a lot more to think about: Which layers work without looking too bulky? Will this dress go with tights? And exactly how washed out does this grey coat make me look?
Like many of us, I seem to always resort to a dependable combination of denim, boots and knits. But if you’re not a jeans or trousers person, figuring out what to wear each morning when it’s cold outside can be even more of a chore. If that sounds like you, don’t fret. I’m here to tell you you can still take advantage of the ever-flattering midi skirt in the depths of winter. Dresses are slightly more complicated—unless they’re made from a particularly thick material with long sleeves you’ll probably need to source a roll neck that works perfectly underneath. But the beauty of midi skirts is that, like jeans, you can just throw them on with your favourite knit and boots and head out the door.
Marilyn knows that a pleated midi never goes out of fashion. We love how she’s paired it with a cropped denim jacket and statement boots for a modern take.
You might be reticent to wear your favourite silk slip, but pair it with a comfy pair of tights and some knee high boots and you’re good to go. Otherwise you can opt for heavier materials like leather and wool which work particularly well for daytime or work events. To make things easier I’ve scrolled through so many styles and listed the best winter midi skirts I could find below— with price points ranging from high street to designer.
Keep scrolling to see them all, either for inspiration for shopping your own wardrobe or for topping up your collection if it needs it.
Denim midi skirts are making a comeback, and as Franny proves they make for a great winter look when paired with knee-high boots and knitwear.
Such a classic cut that can easily transition into spring and summer.
When winter comes around revert to dark florals on deep backgrounds.
Although this style is slightly longer, it’s far too good to miss. Raey usually has block colour offerings but they’ve introduced this slightly playful style into their arsenal for 2023.
A classic day-to-night option.
Chocolate brown is the new black.
Beare Park is a new name to know for 2023. It’s no wonder why with sleek designs like this.
Ulla Johnson does it again. Simply breathtaking.
The brown leather of this Iris and Ink skirt is so rich. It will go perfectly with neutral knits.
Ideal for jazzing up simple black knits.
2023 is going to be all about the full-volume skirt.
We can’t believe how great the price is for this expensive-looking skirt.
You can always count on Christopher Esber for easy-to-wear statement pieces to make any outfit look good.
Slip skirts are everywhere this time of year and even more so in cocoa hues.
If you’re a fan of ’90s styling you’ll love this slinky style with cut-out detail.
Nanushka’s vegan leather is the softest around.
Another classic cut you’ll get years of wear out of.
We love this styled with heels, but it would look just as good with a chunky boot.
Party season might be behind us, but that doesn’t mean events and dinner dates are off the cards. This full taffeta skirt is a lovely option for any upcoming occasions.
A whimsical style you can easily pair with knitwear.
A perfect back-to-the-office skirt.
Keep your eyes peeled for the release of this gorgeous Max Mara piece.
Such a classic.
This skirt could easily pass as designer. Look at the box pleat detail and the weighty fabric.
