For Spring 2027, Miuccia Prada and Raf Simons built the entire collection around the skirt, showing just how much the same garment can change depending on what you put around it. We all know how much Miuccia loves her skirts, she has famously described the skirt as being “like a T-shirt”: easy, familiar, something you can wear with a jumper or shirt (or apparently just a bra!) without too much fuss. But is it really that easy??
However it was Kendall Flavin latest post that gave me the idea for this newsletter. She made a very similar point, just through a different comparison: instead of treating the skirt like a T-shirt, she argues that we should style it as we style jeans. Easy, everyday and casual.
Which got me thinking… because I have always treated skirts a little bit like that. I love a skirt. In fact, I normally find skirts easier to wear than jeans. Jeans are supposedly the ultimate easy wardrobe staple, but when you have a smaller waist, bigger hips and a bum, they do not always sit quite right. Kelly Williams gives really good advice here about how to wear “hard pants” — aka jeans — when you would rather be in soft trousers.
So a skirt has often been that for me, that easy pull-on trouser. But I know that skirts are super easy to wear in the summer. Add a T-shirt, maybe a flip-flop to take the prissiness out of it, and you are done.
Autumn is where things get more interesting…
Once the temperature drops, how do you keep a skirt feeling easy and effortless rather than suddenly turning it into a lady who lunches?
As an avid skirt wearer, I realised there is actually quite a lot I want to say about this, so rather than cramming every skirt thought I’ve ever had into one enormous newsletter, I am turning this into a little series on how to make skirts feel as easy as jeans [or insert your comfy bottoms of choice here].
I have also started a Pinterest board for this series, where I will be pinning all the skirt styling references, runway looks and random outfit inspiration I find along the way. You can follow if you want to see the visual side of all this unfold in real time.
We will get into T-shirts, oversized layers, sporty jackets, big cosy jumpers and all the other things I use to make skirts feel less precious. But I want to start with footwear, because this seems to be the thing that trips everyone up.
As soon as I asked in the subscribers’ chat about skirt-styling dilemmas, Emma sent me this message, and I think she summed up the problem perfectly.
And that is really the question, isn’t? How do you make skirts work with practical shoes without the proportions suddenly feeling a bit off?
However my first instinct is always to say: do not overthink it! An unexpected shoe can bring the right bit of friction the outfit needs. I now, that you subscribe for facts, so I am giving you all the facts!
1. The easy lengths: anything above or just below the knee
If the skirt finishes above the knee, you have plenty of leg showing, which gives you more room to play with footwear.
Trainers, loafers, ballet flats and chunkier shoes can all work because there is enough visual space between the hem and the shoe.
Socks are your friend here. Instead of leaving a random strip of bare ankle, let the sock become part of the outfit.
A loafer with a visible sock — even better if it is a pop of colour — can make the whole thing feel much more deliberate.
This is why I find shorter skirts so easy to style. You can go any direction you want to go: delicate, chunky or slightly masculine just by using the right footwear.
2. But what about the midi?
Midi skirts tend to be a bit more problematic to style, specially for the colder season. And the issue is not so much the shoe itself, but the little section of leg left between the hem and the shoe.
If the skirt ends mid-calf and the top of your boot finishes at the widest part of your calf, you can end up creating several horizontal lines very close together, which is often what makes the proportions feel awkward.
With a midi, I usually prefer going for any of the following:
Keep the shoe low enough that you see a clear stretch of ankle.
This is why midi skirts tend to look so good with kitten heels, pointed toes, ballet flats, slim loafers or a sleek trainer. Anything that keeps the shoe relatively low and shows some of the top of the foot helps the leg look longer and cleaner, rather than cutting it off at an awkward point.Go high enough that the boot disappears underneath the skirt.
This is where knee-high boots really earn their keep in autumn. If the boot disappears under the hem, you avoid that awkward little strip of calf between skirt and shoe, and the whole line looks much more continuous.
Outfit 1: Low, slim shoe = clean line.Outfit 2: Boot disappears under the hem.Outfit 3: Chunky trainer = deliberate contrast. Use a sock to bridge the gap.
This one deserves its own section, and its below!Go chunkier on purpose.
A heavier trainer, loafer or shoe can look brilliant with a midi skirt, especially if the skirt itself is quite feminine. That contrast is what makes the outfit interesting. The only catch is that you may need to get used to the proportions at first, because it can look “wrong” just because your eye is expecting something slimmer.
3. The shape of the skirt matters too
Sometimes it’s not so much about the length of the skirt as the shape. That can completely change which shoes feels right.
We could get VERY deep into this, but I want to keep it fairly simple and useful. If you still have questions, comment, email me or drop them in the subscribers’ chat. Or, better yet, book a session with me!
Full / A-line skirts: they can usually handle more weight underneath. Loafers, chunky trainers, boots and sturdier flats work well because the volume of the skirt balances the shoe.
Straight / column skirts: tend to look best with a cleaner shoe shape. Slim trainers, loafers, ballet flats or a boot that disappears under the hem to keep the line feeling sleek.
Slip / bias-cut skirts: this is where contrast can be really useful. A trainer, loafer or heavier boot can stop the skirt feeling too dressy or precious, while a slimmer shoe keeps the whole look cleaner and more elegant. It really depends on the mood you want
Pleated skirts: can go either way, I find pleated skirts to be super versatile, just like A-line skirts. A slim shoe keeps them polished; a chunkier shoe makes them feel more edgy, pick your poison!
Mini / short skirts: the easiest of the lot. Because there is more leg showing, you can usually get away with a chunkier shoe, boot, sock or something more masculine as we saw above.
The Little Nerdy Styling Details
I am off for a week from Sunday, so there won’t be a separate paid newsletter this week or next. Instead, I am going a little deeper into what to look for when a skirt-and-shoe combination still feels a little off, and let me tell you, I went DEEP!
socks and how they bridge the gap
anklets for taking down the sweetness
why slits matter more than you think
tights as part of the outfit, not just because it’s cold
why a few centimetres of hem length can change everything: with a very specific visual guide
