There are few pieces that are true wardrobe staples, but it is safe to say that the midi skirt is definitely one of them. No matter the season, its versatility and simplicity ensure it remains on the rail year-round.
Come rain or shine, you’ll find me in a midi skirt of some kind, but for people who are less obsessed with the style, winter in particular is an excellent time to don them—they look excellent with boots and can easily be layered up on your top half to ensure you’re warm. Plus, the current selections from high-street retailers and designers are vast and there are many impressive and considered shapes that have a timeless appeal, so there’s a style for everyone.
Over the last few years hemlines have dominated the runway and this season designers swapped barely there mini lengths for their longer (and more voluminous) counterparts. “On the knee” is a popular fashion category and styles from tailored skirting to pleats and airy cotton voiles are infiltrating our feeds.
When it comes to midi skirts, styling opportunities are endless. Pair a midi skirt with a knitted top and juxtapose fabrications (wool and cotton, for example) or mix and match textures. I’m particularly fond of the exaggerated midi skirt and have taken to pairing it with streamlined tops to appease my 2010s obsession with all things 1950s. Though it may seem dated, pairing a full skirt with tailoring and streamlined top-half pairings brings it back to 2023 and gives it a modern update.
Let’s not forget the classics, either. Column slip skirts reappear every spring and the classic denim midi skirt is also a popular style right now, and we expect to see it through next year, too. If you’re a fan of midi skirts keep on reading for some of my favourite investment pieces and outfit inspirations for how to wear a midi skirt this season.
Style Notes: Neutral lovers – this is one for you. If ever you’re looking to enhance your outfits with subdued colours, mix muted tones for some interest. This is one to keep in your arsenal for those wind-swept days.
I’ll be styling this knit with jeans and heels, too.
You don’t have to retire your linen midi skirt now winter is here. This option is the perfect medium between casual and ‘dressed up’ depending on your footwear choice.
A chic saddle bag with an adjustable handle, so you can take it from day to night.
Everyone is hankering after a pair of ecru mary-janes at the moment and Charles and Keith’s shearling-trimmed offering well and truly has my heart.
Style Notes: I love how Karina has paired her slip midi skirt with a tailored blazer and sculpted top. Size up on the blazer to really nail that relaxed-fit look. At this time of year, this is definitely a fantastic party look.
On the hunt for a blazer? Arket is the place to go.
If you look after this piece it’ll last for years! It makes the best layering or standout piece.
Black and brown is such an elevated pairing.
Bottega Veneta’s sardine is spectacular. The hammock style and gold handle is a modern update of the Jodie.
Style Notes: With these chillier days, we’re welcoming sartorial style with open arms. Sandwich luxe leather midi skirt between a crew-neck sweatshirt with a pair of patent leather heeled boots and you’re ready to head out the door.
Basics like this will work with everything in your wardrobe.
This colour will work just as well with neutrals as it will with brights.
How timeless is this saddle bag? It’s set to be a true classic in your accessories collection.
I love the simplicity of these.
Style Notes: A denim midi has become a constant throughout the year, and we’re expecting it to stick around through 2024 too. Whilst there’s plenty of ways to style it, we’re particularly impressed with Taffy’s choice to pair it with a chunky ribbed knit jumper and elevate it further with some sleek leather boots.
This knit is a winter wardrobe basic – plus points for the raised seam design
I predict this versatile skirt won’t be in stock for long.
A playful take on classic hoops.
Updating your boots this season? With a square-toe and stacked wooden heel, these leather sock boots from Reformation are a great option.
Style Notes: The juxtaposition of textures in this look is magic, from the starchy denim jacket to the supple skirt and ruched boots. It’s a look that can transcend from the office to post-work events and date nights.
I would believe you if you told me this was a designer piece. Style tip – belt it at the waist for extra definition.
Long sleeve tops are undoubtedly a layering must-have in the colder months. The round neckline of this style is best suited for the above outfit as it’ll make the lapels on the jacket stand out.
A leather or denim midi will help keep this look weather-appropriate.
Tie the look together with this twisted buckle suede belt.
I love Roop for sustainable, stylish (and playful) bags. This handbag will go with any and every outfit.
Isabel Marant boots have been on my wish list for years. The buttery hue and suede fabrication of the Lipsa style is a match to behold. It’s a piece I would wear year-round and never tire of.
Style Notes: A crisp shirt will be your best friend during the transitional weather. Style with a sleek midi skirt and a pair of glossed leather ankle boots, or dress down with low-top trainers.
This blue striped shirt is set to make any outfit look put-together. Heading into the office? Loosely tuck this M&S number into a tailored midi skirt for a smart yet fashion-forward outfit.
Every wardrobe needs a tailored skirt in their wardrobe in my opinion.
The perfect everyday hoop certainly does exist and it’s this Otiumberg style.
Crafted from rigid leather to create a structured silhouette.
From jeans to skirts, these timeless Stuart Weitzman ankle boots will go with so many things.
Style Notes: Grabbing a coffee? Running errands? Heading off on a shopping trip? Nail the dressed-down aesthetic with a washed denim midi skirt, partnered with a crew-neck T-shirt and a knit cardigan. Accessorise the look with some comfy trainers, a leather shoulder bag and cat-eye sunglasses.
You can’t go wrong with a relaxed-fit T-shirt, and this option sports a loose-fit, dropped shoulders and raised seams.
The distressed hem adds a relaxed feel, though its still easy to dress up.
I’m adding this cardigan to my wish list ASAP.
You’ll get plenty of wear out of Demellier’s Midi New York bag.
Adidas are championing the sneaker game this season and these Handball Spezial don’t disappoint.
Style Notes: Add a touch of colour to your wardrobe, in a minimalist way, with a statement midi skirt. Make the outfit autumn-ready with a relaxed-fit T-shirt and leather jacket.
Ganni T-shirts never fail.
Topshop has some great skirts and this stand-out option can easily transition from office-ready to after-work drinks. For an off-duty look, pair with chunky trainers or dress it up with a pair of platform mules.
The biker jacket trend is still in full swing and, luckily, this cropped faux leather offering is still in stock.
This easy shoulder bag will go with so many outfits.
If you’re looking for a chunky trainer that prioritises comfort, New Balance is your answer.
This piece was published at an earlier date and has since been updated
Next Up: It’s Official: These 5 Trainer Trends Are Set to Replace White Sambas in 2024