You know how much I love a skirt, and because they are very much having a moment right now, I have decided to make it my business to solve all the annoying little things that stop us wearing them more.
Too pretty? Too dressy? Not sure how to make them feel cool, easy and actually wearable in real life?
If you have not read Part 1 yet, that was all about the big pressing issue: what the hell do I wear on my feet? Start there.
If you have already done your homework, welcome to Part 2. This time we are looking at what to wear on top to make skirts feel more exciting, modern and a little less precious.
And right at the end, paid subscribers are getting some quick fixes for when the outfit still is not quite working, plus some of my current Vinted favourites, which are very, very good and I am slightly territorial about sharing…
But first, let’s get into this!
1. Let the Skirt Be the Star
One of the easiest ways I make skirts feel more everyday is by letting the skirt be the star of the outfit and keeping whatever goes on top much more casual.
Think satin, tweed, silk, pleats, animal print, anything slightly ladylike or special… paired with the kind of T-shirt you would normally throw on with jeans (or your pyjama bottoms!)
My favourite version is a slightly oversized vintage graphic tee and I am obsessed with how Jess from Wear Some Fun finds the most random vintage T-shirts on the internet, down to the very specific search terms she uses.
If graphic tees are not your thing, a plain T-shirt in your favourite neutral works just as well. A white, grey, navy or black tee can be exactly the palette cleanser a busy skirt needs. I really love how Sogole Kane styles her column skirts with a slightly oversized long-sleeved T-shirts, which feels minimal, casual and a little more current than the classic short-sleeved version.
I also like playing with the tuck rather than doing anything too neat. Sometimes I just tuck the top slightly to one side so you still get a bit of shape without making the whole outfit feel too done. Other times I leave it completely loose. Depends on my mood and level of bloatiness.
Some quick styling tips:
Use the T-shirt to make the skirt feel like jeans. The more polished, ladylike or precious the skirt is, the better a very ordinary tee can work with it. The classiest tweed skirt with the slightly cheesy I ❤️ NYC T-shirt from the Chanel Métiers d’Art is the perfect example: something lady-like vs something you might buy as a joke.
If the skirt is already doing a lot, keep the T-shirt very simple. A plain white or grey tee works brilliantly with animal print, checks, shiny fabrics or anything visually busy.
A long-sleeved T-shirt can make the same formula feel more current. Especially when the skirt is straight, column-shaped or a little severe. It feels slightly more directional than a classic short-sleeved tee.
Tucking changes the mood completely. A neat tuck, like the Maison Margiela look above, makes a graphic tee work beautifully with a pencil skirt because the waist stays defined and the proportions feel sharper. A loose or side tuck makes the same idea feel much more relaxed.
Use a belt if you want the T-shirt to feel more deliberate. Particularly with pencil or straight skirts. The belt creates a proper break between the casual top and polished skirt, and adds a bit of visual weight around the waist. If you are worried about your tummy showing, that extra structure can actually help the fitted silhouette feel more pulled together and less exposed.
Let the T-shirt be a little bit (or a lot!) wrong. A vintage graphic, faded logo, random slogan or slightly oversized fit works better than something pristine because it gives the feminine skirt some real friction.
The Outfits
Two ways to ground a skirt via the top half: slightly sporty with a band T-shirt on the left, cleaner and more structured with a simple long-sleeved tee on the right.
Outfit 1: Soeur jacket / Me + Em multi-position necklace / Preloved Prada skirt / New Balance trainers / J. Crew white leather bag / H&M graphic t-shirt
Outfit 2: Preloved Prada skirt with belt / COS long sleeve t-shirt / Celine sunglasses / Preloved Acne Studios biker jacket / Toteme zebra shoes / COS leather bag / PDPaola earrings
2. A Touch of Sportswear
If you are a millennial, you probably wore the hell out of trainers with dresses and skirts back in the day (maybe still do?), so this should feel fairly familiar. What changes the mood now is taking that idea one step further and adding an obvious sporty element on top.
It makes skirts feel more casual and wearable, but it can also make that old skirt you’ve had forever suddenly feel much more current.
And yes, windbreakers and rugby shirts are everywhere right now. I have to admit I gave in and already bought a windbreaker from Zara, and I have already worn it loads because it is super light and adds something unexpected to dressier pieces.
But if you are tempted by the trend and not fully committed, do not immediately go out and buy a collection of windbreakers and rugby shirts. Experiment with what you already have. Maybe it’s an old Adidas tracksuit jacket you only wear to the gym, an ancient bomber you found in a charity shop, or even your partner’s hoodie. Anything with a vaguely sporty feel can work.
A few things I keep in mind:
Keep the sporty element to one main piece. If the track jacket, rugby top or windbreaker is doing the sporty work, I usually let the rest of the outfit go in another direction.
Add something polished back in. A sharp blazer over a rugby top, black accessories, a structured bag or a pair of diamante earrings can stop the outfit from going too ‘running a marathon in my skirt’.
If the top is sporty, keep the footwear sleeker. As much as I love a chunky trainer with a skirt, I would probably skip it here and go for a loafer, ballet flat, slim boot or something more refined.
Let the sporty piece feel slightly out of place. That is often what makes the skirt feel fresher. If everything matches too neatly, you lose the little bit of tension that makes the outfit interesting.
The Outfits
On the left, the rugby top makes the satin skirt feel much less precious, while the leather blazer keeps it from going too sporty. On the right, the striped tee and pink utility jacket give the pleated skirt a much more casual, slightly unexpected direction.
Outfit 1: COS rugby shirt / COS layered skirt / Celine sunglasses / COS leather blazer / COS bag / COS ballet shoes / COS hairpin
Outfit 2: Arket Harrington jacket (sale) / COS stripe t-shirt / Massimo Dutti pleated skirt / Demellier Stockholm bag / Me + Em diamante earrings / Loeffler Randall tall boots
3. Bring in Something Utilitarian
Another way I like to make skirts feel less pretty and more like a pair of jeans is by adding something that feels a bit more practical, structured or uniform-like on top.
Think barn jackets, denim, suede, leather, utility jacket, boxy blazers, even a Napoleon-style jacket. Basically, anything that brings a bit of weight or structure to a skirt that might otherwise feel too soft, feminine or polished.
I especially like this with anything super cute and pretty: satin, silk, minis or fuller skirts because the contrast is so easy! The skirt brings the movement and softness, while the jacket makes the whole thing feel much easier and relaxed.
And again, I would not rush out to buy the exact jacket everyone is wearing. Look at what you already have that gives you the same feeling: an old denim jacket, a slightly battered leather one, a military-inspired coat, a utility shirt or a blazer with strong shoulders.
And if you live with a man, even better, raid his wardrobe! Menswear versions often have the boxier shape and extra weight that works brilliantly with a skirt.
This is also one of those trends that is especially good second-hand, so go to your local charity shop and see what you can find.
A few things I keep in mind:
Let the jacket have some structure. Boxier shapes, heavier fabrics and strong shoulders work especially well against a skirt with movement.
Do not make everything polished. If the jacket is already quite formal or decorative, like a Napoleon jacket, keep the rest simpler.
Use texture to do some of the work. Suede, denim, waxed cotton, vintage leather and tweed all bring a bit of visual weight without needing lots of extra styling.
Keep the shoe relatively simple. Loafers, a chunky boot, ballet flats or a clean trainer let the jacket and skirt do the talking.
Look for the general mood, not the exact trend piece. The useful bit is the structure, utility or uniform feel. You probably already own your version of it.
The Outfits
Two ways to make a skirt feel less precious with a practical layer: leather and denim on the left, quilted jacket and loafers on the right. The skirts stay feminine, but everything around them feels a bit more grounded.
Outfit 1: Soeur jacket / Ami Paris denim shirt / Flore Flore t-shirt / J.Crew skirt / Loeffler Randall chunky boots
Outfit 2: Barbour jacket / COS merino wool top / COS skirt (sales) / J.Crew snake print loafers / Massimo Dutti suede bag / COS mismatched earrings
For paid subscribers, I am getting into the bit I always want after reading a styling post: what to do when you try the idea and it still somehow looks wrong.
First, a few quick styling fixes for the most common skirt problems. Then I’m sharing some of my favourites on Vinted: a few statement jackets, chunky boots inspired by Claudia Winkleman, and some very good deals on loafers by The Row and Dries Van Noten.