A few styling tips for men wearing skirts

So previously I gave you some tips for buying skirts; now we come to the real nitty gritty. This pages has some styling tips gleaned from my own experience in the north of England, just in case you think I live in some metrosexual mecca like Brighton. The other day I went to a football match in a small village twenty minutes from where I live wearing grey nail polish and Jesus H Christ, the looks I got. I couldn’t have been stared at more if I’d gone in full Trixie Mattel drag (I might do that next time).

A reminder of the caveat

My style is gender-neutral, gender-free and androgynous, whatever synonym works for you. I don’t like to be read as too masc or too femme and dressing too far in one direction generally kicks my gender dysphoria into action too. Accordingly, the tips I give you now are based on that outlook and everything below is just my opinion (albeit based on lived experience). 

If you’re AMAB and want to go out looking high femme, then all power to you but I don’t have any tips explicitly for you here. It’s a shame that we have to consider these points and obviously we’re not shaming anyone for choosing to go full femme. Hopefully in the near future fashion will be fully democratised and we’ll have full equity of dress. But we don’t live in that time, and I firmly believe there’s a way that Hims and Thems can dress which slowly starts to cultivate acceptance for gender-free dressing with firm foundations to build on. What we do now, we do for those who come after us, and representation matters. We good?

What lengths of skirt work best for men?

Here’s my humble opinion: avoid skirts that finish too far above the knee. Aim for knee length or below is my advice unless you can pull off an athleisure look. Shorter skirts, especially ones that are pleated or flared, can have very strong schoolgirl connotations and that’s really something that you want to avoid if you’re hoping to avoid strong abreactions.

Skirts that finish just below the knee, down to midi (mid-calf) length, are very reminiscent of the length of a kilt, so you’ll have that on your side. It’s modest, it’s stylish, it shows a bit of leg, but it’s still conservative enough not to trigger any snowflake Daily Mail readers.

LOL at idiots who try slide tackling on astroturf. A knee-length skirt is just enough to cover the gashes and bruises.

A maxi or ankle length skirt can also be both classically stylish and striking. Sarongs are typically around that length and as with kilts that’s more of an accepted length for a traditional man’s skirt. I always think that length looks good when dressed down with trainers.

What silhouettes work best for men?

There is a little chance to show off when you come to pick the silhouette. I always aim for something a little more fitted around the waist and bum. I can still get into jeans with a 29” waist on a good day and through running and football, my ass hasn’t become completely flattened (although it might if I spend much more time on the PS5). So I don’t mind showing it off a little with something more fitted. Frankly it’s good for the ego for someone to tell you that you have a nice bum (or at least, it is at my age!).

I always steer away from anything more fitted after that. If it’s so tight around the thighs that you have trouble walking, then I think that’s probably too much (or at least it is for me). At the same time, I don’t want anything too flared lest an unfortunate gust of wind rob me of my modesty. I also avoid anything that will slide up when I’m sitting, or expose so much of my thighs that I need to cross my legs whenever I’m sitting.

What style of skirt works best for men?

If I’m going casual, then there is no doubt that the cargo skirt works best for me. You’ll remember of course that a cargo skirt is just a non-bifurcated version of cargo shorts, and comes with the full range of pockets, flaps, D-rings, and everything else. Crucially, cargo skirts almost always come with a working zip or button fly! Definitely not something you want to overlook. I have a couple of knee length cargo skirts and there’s no doubt that some of them, on casual glance, just look like shorts. Cargo skirts give you the advantage of functionality via pockets and fly that are missing in other styles.

Something to look out for: as you start to accumulate a wardrobe of skirts, look out for the ones that have fake pockets, especially on the bum. If you want to hear a rant, ask your female friends and family members about pockets on skirts and dresses – but stand well back.

What colours work best on skirts for men?

I’m very much a fashion minimalist anyway so probably not the best role model for this particular answer. My wardrobe is a sea of black, white, grey, blue, occasional beige and nude, occasional green, and a yellow jumper. I find sticking to the classic neutrals is the way forward. In these pictures I’ve deliberately styled skirts with a neutral white sweater in a basic cut so that the skirt stands out. You could take attention away from the fact that you’re wearing a skirt with a more interesting statement top or footwear; or you could choose to go for a more colourful skirt, or one with a print, and pair that with neutrals. That would certainly highlight the skirt.

Should I wear a skirt over trousers?

Hell yeah. Ignore people who say it was a 90s trend, fashion is perpetually on a loop. Recently my daughter and I took her two grandmothers to see The Ladyboys of Bangkok (and if you haven’t seen them yet, then you haven’t lived) (the Ladyboys, that is, not the two grandmothers although they’re fun too). I was wearing my Jaded London black coated denim kilt over a pair of black coated jeans with the same finish and the effect was great (even the nannas said so). It’s kind of a gateway drug or stepping stone to the real thing. On the Jaded website they’re styled with matte baggy jeans and I prefer a more fitted look, but you get the idea of how they can be styled together.

What is your number one tip?

If I were to recommend one thing to first time skirt wearers, I’d say choose a knee length cargo skirt in a neutral colour, and pair it with a white tee and trainers. Honestly, you can’t go wrong, it’s an effortlessly simple combo that doesn’t look like you’re trying too hard. That’s definitely my number one tip.

And finally

A reminder that these are just tips that I have found work for me. I’m not expecting you to copy them exactly, no more than I am saying that people who do something else are wrong. They’re not. Ideally everyone would dress to please themselves. What I’m hoping to give you here are some pointers about what to think about.

For example, if you were much shorter than me you might find a below knee length skirt makes you look shorter and squatter; a shorter skirt would make your legs look longer. Similarly a much taller person might find a knee length skirt makes their outfit look out of proportion. And don’t forget the effect of layering – a long sweater over the top of a short skirt might make the skirt look even shorter.

So, take these tips, consider the questions for yourself, and use this as a base to build from rather than a set of instructions to be followed unquestioningly. And have fun – fashion is about taking chances, experimenting, daring to be bold while at the same time of course wearing something that you’re comfortable in. But don’t just take my word for it…