Although the times they are a-changin’, it can still be pretty daunting for Hims and Thems to wear a skirt in public even when there are lots of reasons why one might choose to.
For example, as I write it’s 28 degrees outside (or it was when I originally wrote that line back in the late summer) and I’m wearing a Y2K-style lightweight nylon utility skirt. If I was wearing jeans instead, there are a couple of very good reasons to wear a skirt and they would be a lot stickier and sweatier.
In the end there are only two reasons that matter when it comes down to men, masc and AMAB people wearing a skirt:
- You want to wear a skirt
- You don’t want people to see your pants (which hopefully would be some nice lingerie for men, right?)
I can tell you from personal experience that the first couple of times you buy and wear a skirt, it can be quite challenging. Happily, you’ll soon realise that you’re completely irrelevant to the continued existence of the universe and almost nobody gives two hoots what you do! Apart from the obvious existential desperation that this induces, it’s actually extremely liberating once you realise what you can get away with. Wasn’t it H from Steps who said, “you have nothing to fear but fear itself”? Well, it was him or Teddy Roosevelt, I forget which and they’re so easily confused.
So in this post, I thought I would give you some tips which will help you both shop and wear a skirt for the first time. But first, a caveat.
A caveat
Everyone should wear whatever they choose. Seriously. Wear what gives you joy. Ignore what fashion blogs tell you; there are only five categories of clothes and they form the basis for the few rules that you actually need to remember.
- There are clothes that fit you, and clothes that don’t. Wear ones that you can fit into.
- There are you clothes that you like, and clothes that you don’t like. Wear clothes that make you happy whenever you can.
- There are a few outfits that will probably get you arrested, but they’re pretty obvious and easy to avoid. Don’t go to a state funeral in just a rainbow strap-on and body glitter wearing Mariah’s The Emancipation of Mimi album sleeve as a hat, and you’ll probably be fine.
Really, it’s the first two that you should concentrate on. Me, I swerve postgender. That’s my schtick. I deliberately aim to avoid clothes with overt gender markers, so if I wear a skirt and heels, I will aim for something neutral (a knee length skirt and chunky heels) rather than something that can be read as femme, such as a tight vinyl pencil skirt with stilettos.
I do this because postgender is my style. I’m not making a values judgement on Hims and Thems who want to wear a micro skirt with whale net holdups and 9” stripper heels. You do you, gurl. But the info and advice that I give here is based on my more neutral style. If you wish to start with something that most people would read as femme, may I recommend consulting the Instagram feed of someone like the amazing Ray DeForest instead? There’s a huge amount of both inspiration and wisdom on their feed.
How to buy skirts for men
We should all be buying less clothes, and especially less new clothes. And that puts us in a win-win situation because we can use the anonymity of online buying to get over our shyness of browsing in Victoria’s Secret Pink (also it means we don’t buy clothes from VS, which is another win). Buying pre-loved clothes online often means that you’re spending a lot less than new, although not always – proper vintage is expensive, and it’s not uncommon to see kids buy something on Ebay for a fiver and then flip it for thirty quid on Depop, calling it “vintage”. Something to be aware of.
The flipside is that there’s no try before you buy; you can’t see the quality of what you’re getting; and that generally women’s clothes come in women’s dress sizes rather than S/M/L etc. so you’ll need to get your head round that. As mentioned elsewhere, the only thing more inconsistent than women’s dress sizes are Jadon Sancho’s performances for Manchester United, so be prepared to buy a couple of duds while you’re figuring out what sizes you are in each brand (tip: don’t buy Zara unless you’re six feet tall and built like a pipe cleaner on a diet). You’re unlikely to find actual men’s skirts on the second hand sites, just because there are so few available as new. So, concentrate on the gender-neutral end of women’s skirts.
Places to buy skirts for men
Here are some websites and apps to get you started – you’ve probably heard of most of them:
Watch out for ebay
I am going to give you a caveat about Ebay. It hasn’t yet occurred to them that Hims and Thems might choose to wear skirts, so they’ll treat it as a typo for “Men’s shirts”. You’ll also get a lot of false positives from people who can’t spell “shirt”. Just search “skirts” in the women’s section.

Cow have got it sorted
Cow have these things that are like websites except they’re made of bricks and plasterboard and you can walk into them and pick things up and talk to real people. They’re amazing and I hope this idea catches on. If you can find a Cow (not a cow, that would be silly) or another curated vintage/pre-loved fashion outlet nearby, definitely check it out.
Sweeping generalisation I know, but they tend to be staffed by younger people who actually care both about fashion and the planet, and simply don’t give a flying fuck that a bloke is trying on a skirt. Seriously, I can and do wander round Vulgar in Sheffield* trying on cargo skirts and dungaree dresses and no one cares. Even if you don’t try it on, you can always say it’s a present for your girlfriend and the staff will play along. So if you can find one of these real life websites, definitely go browse them.
* The green cargo skirt I’m wearing in the main image at the top is from Vulgar. I have no idea who it’s by, there’s no label. 95% of the times that I go out in a skirt, I’m wearing a cargo skirt like this or a kilt.
I’ve bought a skirt and I don’t like it, now what?
If you buy something sight unseen and it doesn’t fit, or doesn’t suit you, or it is too lightweight and gives you a Marilyn Monroe moment just because someone looks in your direction, and once again I’d like to apologise to the people behind me on the escalator in Sheffield that one time when I learned that lesson the hard way, there are still options.
Regift it
If you know someone who will like it and wear it, gift it. Don’t even wait for Christmas, birthday or some other annual gift-giving festival, just make someone feel special and give them a present and a compliment. There, don’t you already feel better?
Resell it
Put it on ebay or Depop or something, and get some of your money back.
Use it for a sewing project
Long shot I know, but it’s definitely an option for some of you crafty types.
Recycle it
Recycling fabrics cuts greenhouse emissions but you need to be sure that the clothes you donate are getting recycled, and not just parcelled up and sent to a developing world country.
Donate it to a charity for the homeless
Assuming it’s practical and you didn’t buy a sheer sequinned micro-mini.
Give it to another charity
This should be your last option (because throwing it away should not be an option at all). According to the EPA 84% of donations end up in landfill and incinerators, so if you buy something and it’s not perfect, it’s probably better to find another option than giving it to charity – chances are, it won’t be fit to sell.
I’ve bought a skirt and I do like it, what do I wear it with?
In a future post I will list some of the other role models and fashion influencers who are wearing skirts; I’m also going to list some of the outlets who are selling skirts for men, but be prepared to put a weekend’s overtime in before you buy from some of those is all I’m going to say. My timeline of men wearing skirts is another page you could check out, as I list some of the notables appearances of blokes in skirts.
Up next though, I’m going to give you some simple tips on how to wear and style skirts that have worked for me.