It's time to make the skirt work. Difficulty: Dude.

February 7, 2013 6:03 AM

So a couple of friends are putting on a night called Skirt, and in the progressive / queer-positive spirit of the event, guys are being encouraged to come wearing one. I'd like to do it, and I'd like to make it look damn good. Skirt-wearers of MeFi, please help me.

Further particulars: I'd like to end up with a look that's not "100% masculine kilt-wearer" but not too femme; I'm liking what Marc Jacobs does in this direction pretty well. I'm 6'2, have a 32 inch waist, a slim / toned build, and am pretty masculine looking (beard). Advice on any or all of the following would be greatly appreciated:
- type / cut / style to wear
- what other clothes to pair with
- places to buy in London in the next 24 hours or so
- shopping etiquette
And anything else you can think of - this is new and strange territory for me, filled with unknown unknowns...

posted by ominous_paws to clothing, beauty, & fashion (46 answers total)

I have seen good effects done with sarongs - depending on your coloring, maybe some bold colors in silks, paired with a flat, tighter top that can stretch across your chest.
posted by corb at 6:11 AM on February 7 [4 favorites]

Ooooh...like the sarong idea.....that would be very cool and different.... Was coming here to suggest a basic pencil skirt....tight, black, but with some AMAZING shoes. if you are fit you probably have great looking legs.....show them off!!
posted by pearlybob at 6:14 AM on February 7

If you have hairy legs and don't want to shave them, I recommend opaque stockings. Much less commitment than shaving, and takes it out of kilt territory. (Leg-shaving only came into vogue once stockings went out.)

Now then: women who read girly magazines know that you're supposed to wear certain types of dresses and skirts with certain body types. As a man, you are probably either a 'wedge' or a 'rectangle' according to that guide, depending on how wide your shoulders are. Select accordingly.

Once you know what style you need, try a thrift shop. No one cares who you are or what weird things you try on at a thrift shop, plus: cheap! Your waist is likely wide enough that you may need to check the plus-size section for skirts. The tights you can get at any department store, they're one size fits all. People will assume they're for your girlfriend.
posted by showbiz_liz at 6:15 AM on February 7 [5 favorites]

Oh, for shoes: oxfords are gender-neutral right now, so I'd wear some of those if you have 'em.
posted by showbiz_liz at 6:16 AM on February 7 [1 favorite]

A friend of mine (male) looked great in a long cargo skirt, similar to this but in khaki, that he used to wear around like it was nothing.

That is the only advice I have. Despite being a lady, I have no other knowledge on skirts.
posted by chiefthe at 6:16 AM on February 7 [3 favorites]

I don't think you could go wrong with a black pencil skirt. It's flattering, easy to fit with a slim build, and goes with everything.

Make sure you look for one with a decent vent cut at the bottom (sides or back) so you'll have enough freedom to walk.

I can't speak to London specifically, but in my experience gentlemen who want to try on "lady clothes" have a little more freedom to do so without awkwardness at vintage/thrift/secondhand shops.
posted by pantarei70 at 6:17 AM on February 7

I'm thinking that a thrift store or second-hand store might be the way to go here. You're pretty slim, so finding a skirt shouldn't be too much of a challenge.

H&M is a pretty good place to go as well.

Here's a nice black one, a might puffy, but if you butch it up elsewhere, it might work.

Here's a simple one in gray. Might be a hair short, especially on you!

This is a longer maxi skirt from Top Shop. Since you're tall, it'll cover your legs and not look too young.

I'd go with black or dark gray. Go with something simple. The man skirts on the runways are kind of bulky, or they come off kiltish. A wool, straight skirt or A-Line would be a good choice.

Matching Knee Socks and loafers will make it look normal and masculine on top. For above the waist-line, a crisp white shirt, a snappy tie and a zip-sweater over it should make you feel fashion forward.

Scroll down on this blog for some ideas on what I'm thinking.


Sounds like a fun event!
posted by Ruthless Bunny at 6:23 AM on February 7 [1 favorite]

You're on the right path. Straight skirts work on men. Here's how I'd cheat on this one, given your build: the t-shirt skirt. If you have the right t-shirt—it has to be thick enough and not blousey or baggy and just the right size in general—you can stretch the neck to make a waist and tuck the short sleeves in as pockets.
posted by RJ Reynolds at 6:25 AM on February 7 [1 favorite]

If you're looking for shoes to go with the skirt (I am all in favour of the pencil skirt idea suggested above, although it will be quite unexpectedly restrictive! knees together when leaving a car, girls! :D), a couple of my genderqueer/drag friends swear by Evans for both shoe sizes and clothing.
posted by halcyonday at 6:26 AM on February 7

I wanted to say "A-line" as soon as I read the question – it's the general shape of a kilt, disregarding the pleats and such. It's flattering on pretty much everyone. Depending on the fabric, it can look pretty much however you want it.

A straight skirt (pencil skirts are straight skirts) would also be good, yes; also easy to style to your tastes.

Pair with: I say no need to worry about unshaven legs, go for it. Then again, I am a woman who practically never shaves her legs and attends the opera in Monaco all hairy and stuff, so I know full well how mileage varies ;) (never had any remarks on my furry legs, fwiw, only on my height)

Shoes, chunky is fun. Lace-up boots give a nice edge, and again you could choose whichever style you like for chunkiness or "mere" edginess.
posted by fraula at 6:27 AM on February 7 [4 favorites]

One thing to keep in mind as you get ready for this is what you'll be doing-- if said night involves any dancing at all, I'd go for an a-line skirt over a pencil skirt, since pencil skirts can be mighty restrictive, especially if you're not used to them. Most of the skirts I see in your Marc Jacobs link have a slight a-line to them, which will give you more freedom of movement than a pencil skirt. The other thing about pencil skirts is that you really need to make sure they fit correctly, which is less true with an a-line skirt. If you do end up doing your shopping in thrift stores, you might find some straight-ish but not super tailored skirts in the suit section, as the bottom halves of older skirt suits.
posted by dizziest at 6:48 AM on February 7 [3 favorites]

A pencil skirt is usually a great option, though as a man and without the curves (ie. hips) to create some shape it may be weird. For a pencil skirt to look "right" it would have to fit fairly snugly, same as for a woman. That can sometimes make them a bit fussy and not crazy comfortable, depending on the skirt. (and not to be indelicate, any "groin excitement" you experienced over the course of the evening would probably be all kinds of obvious in a pencil skirt...)

An A-line is likely the best and most comfortable option for you. A long bohemian/peasant type skirt would be great too. Pair it with a tight fitting t-shirt and you're good to go.

Re. opaque tights -- my sister's partner wore opaque green leotards at hallowe'en last year. He is a pretty hairy guy but his dark hair still showed through a bit. People thought that he bought "marbled" tights, but it was just his leg hair bunching up and creating dark swirls. Both hilarious and kind of disturbing.

I'm not saying you need to shave your legs... but hey, if you're going to wear a skirt, you may as well go all out.
posted by PuppetMcSockerson at 6:54 AM on February 7

If you go with tights, go with dark color.

Opaque in women's clothing dose not mean what it does in men's clothing.
posted by French Fry at 7:01 AM on February 7 [1 favorite]

Do not shave your legs! Hairy legs are very masculine.

Try to shop during a time of day that isn't very busy.

Find a dressing room with a chair or a bench in it. Try on the skirt, sit down, facing a mirror if possible. Check the fit. 1) Can you sit comfortably? 2) Is the skirt riding up too much? Go one size larger. 3) Are you flashing your junk? Try a longer style.

I like a fitted, collarless dress shirt, very well pressed, and a straight-lined skirt that goes past the knees with a slit on either side. Pair with combat style boots and you will sizzle.
posted by myselfasme at 7:01 AM on February 7 [2 favorites]

I'd look for a trouser skirt or cargo skirt. You'll probably need to wear a belt. A short skirt will display your legs well. I like to wear a black skirt, black top, and bright opaque tights. That would certainly avoid the kilt look, although I'm a fan of kilts in general. Black tshirt, black cargo skirt & burnt orange or olive green tights would look great. Would love to see pics of your choice. Have fun!
posted by theora55 at 7:06 AM on February 7

Maybe you find some ideas here?
(German language website for a brand of skirts designed for men.)
posted by jazh at 7:16 AM on February 7 [1 favorite]

I would like to suggest a maxi, or column, skirt. my suggestion comes from experience. a few weeks ago, my dude friend wore my skirt (the purple one) in a bar, and i think it looked pretty good on him. the shape is strong and flattering, because it just falls straight down to the tops of your shoes. it actually looked really natural and cool, we both thought. this is a really great example of what i mean, via your marc jacobs image results.
posted by iahtl at 7:16 AM on February 7

I immediately picture something straight with a high waist, because if you're slim you've probably got acres of torso you can work with. Something military inspired, with buttons? Or, if you're dancing, a flared military skirt.

If you go with a straight skirt, wearing something on top that emphasizes your shoulders will create a great overall silhouette. A flared skirt works with a slim cut sweater.

Don't shave your legs! I think it's the mix of feminine, masculine, feminine, masculine that makes an outfit like this work. (But maybe that's just me.) Unless you are wanting a drag-like effect, in which case, shave away.

Another tack is to just consider how you normally dress and fit a skirt into it. If you're a tie and jacket guy, go with that and a fitted skirt in the same kind of fabric. Or if you're a jeans and slouchy sweater guy, a denim skirt, t-shirt and cardigan would also look good.

When I was googling for military skirt images, a lot of hits were from Marks and Sparks, so you might try there.
posted by looli at 7:20 AM on February 7 [3 favorites]

I'm picturing a kind of ragged-cut a-line skirt in a jersey material. I like the lace-up boots idea. Having trouble finding an example online, though. I agree that a thrift store is the best place to go -- are you handy? If you can hem to whatever length you want, you'll have more options. Or is there a Ross type store near you? Just keep trying on skirts until you find one that fits good and looks good.
posted by amanda at 7:24 AM on February 7

I have a Macabi. It is good. NB if you need it tomorrow that's not gonna happen but nevertheless it is an eminently practical skirt for all humans.
posted by seanmpuckett at 7:28 AM on February 7 [1 favorite]

I love the idea mentioned above of classic casual menswear on top - a button down with tie/sweater - and a tailored skirt in the same kind of fabric you'd normally wear pants. Then for shoes either boat shoes, driving mocs, or loafers (dressiness matched to the top), knee socks optional with the loafers.

I generally like a manly-man but that sounds pretty hot.
posted by amaire at 7:37 AM on February 7 [3 favorites]

You could look to Fijian policemen for inspiration. They sometimes wear skirts, but definitely don't look like they're in kilts and don't look femme.
posted by The corpse in the library at 7:56 AM on February 7 [2 favorites]

I've done drag a few times and had mixed results with a tight pencil skirt. Unless you want to tuck, and I'm guessing you probably don't, there's a pretty good chance that a tight pencil skirt will show off your gentlemanly area in an unflattering light - wrinkles, gathering, etc. Unless that's what you're going for, I think the a-line sounds like a good suggestion, or something pleated.
posted by ga$money at 8:11 AM on February 7 [1 favorite]

You probably want to also think about what you will wear under the skirt if you normally wear boxers. In an tight skirt boxers are going to be visible and might get bunchy and uncomfortable. And if you aren't use to the short skirts, they could lead to some unintentional flashing. If you decided to wear tights or hose, wearing them underneath your underwear helps keep them in place. And please post a picture or your final look.
posted by florencetnoa at 8:25 AM on February 7

Oh, one other thought. Give some consideration to skirt length and definitely try it on and sit down in it before you commit. The last time I did drag, I thought, "Oooh, short skirt," because, hey, I like short skirts on women so of course that will look great on me, right? Wrong. I spent all night standing because every time I sat down, the hem pulled up over my gentlemanly area and I really wasn't wearing the right kind of underwear to make that look work.

I'm rather pleased to be able to pass on this hard-won, first-hand knowledge.
posted by ga$money at 8:27 AM on February 7 [4 favorites]

Nthing the sarong, because that is just a rectangular piece of fabric that you can play with before the event and figure out how to hack it so it doesn't gape or fall down or do weird things shapewise (it's also very adaptable to whatever particular quirks of anatomy you may have). Also, you can use it as a tablecloth afterwards.
posted by EmpressCallipygos at 8:47 AM on February 7 [1 favorite]

I think everyone's covered the where and what, but I'd like to address a tiny bit of the "how." I think when men look awkward in skirts, it's often because they aren't used to that lack of fabric in the crotch region, and they walk as if they are wearing pants. You'll pull it off best if you can think about keeping your knees near each other more than you normally do when walking and sitting.

When I teach people how to walk in heels and skirts who aren't used to it (men and women) I tell them to visualize walking a tight rope -- you don't literally have to put your feet directly in front of the other, but that's what it'll likely feel like if you're used to walking in a more "pants-wearing" manner.

(Also, as a lady who likes to see men in skirts, I think this idea is awesome.)
posted by pixiecrinkle at 8:48 AM on February 7

Pencil skirts are cut closer to the body than a standard straight skirt, and so I'm not sure how well that would fit a man even if they are pretty slim. Also, because they are tight, they are really weird to wear for the first time if you're not used to them. I have a pencil pinafore skirt and I had to teach myself to walk differently in order to make it comfortable and not rip the thing in two. (In the end, I fell down the stairs at my boyfriend's and split it right down the posterior.) I think that's why many wear them with heels rather than flats, as heels rearrange the position of the legs, bottom and back a little bit.

For a 32in waist you'd probably be looking at a size 14 or maybe a 12. In Topshop you'll be a 14 at least as they cut small. (Mind you, I have a very definitely female shape and if you have little in the way of womanly hips this may not apply.) A LOT of women's clothing is cut very short these days unless you're willing to shop in places that aim their range at a slightly older woman, so you might struggle in places like Primark or New Look which are popular with teenagers. I haven't been able to buy a skirt in Topshop for a long time, but that might be as much to do with my shape as my height, and I have never found a maxi skirt that is long enough for me on the high street. Non-specialist shops class 'tall' for women as 5ft 7 and over - most women's clothing is designed for someone 5ft5 or 5ft6.

You are going to have an absolute pain in the arse finding tights for a 6'2 figure, unless your legs are shorter than 34" on the inside. I'm 5ft10 with big feet (women's sock and tight manufacturers tend to assume all women take a 4-7) and usually have to get XXL which means they are more likely to be looser as they're designed for much larger women, and they wrinkle and slip down, and it's really annoying.

And seconding the thrift shop - where in London are you? When I was in Manchester and charity shopped more often, I would often hear/see trans people coming in to pick up clothing. Also, my male friends would go this route for fancy dress parties that involved drag.

In my experience women are not allowed in men's changing rooms - the same applies vice versa I would assume. Unless you present as female - which I am guessing you don't! - be prepared to not be able to try anything on in the shop unless you're in a store which has men's changing rooms as well. Nothing to stop you buying, heading to the loo in McDonalds to try it on then returning afterwards, though.
posted by mippy at 9:06 AM on February 7

As to the leg hairs poking through hosiery, you could try tamping them down with lots of body lotion.

Since you are (I assume) not accustomed to wearing this sort of hosiery, I have a few thoughts:

1. Buy two pairs in case one pair gets ruined while you are trying to negotiate putting them on. If all goes well, you have a spare for the next fest, or you can donate them to a thrift shop.

2. Be sure your nails and hands are smooth before you even take them out of the package.

3. Be sure that your heels are very smooth before attempting to put them on. I routinely blow heels out of pantyhose and knee-highs.

Are traditional Irish or Scottish kilts out? They'd have the advantage of being able to wear socks. And they are sooo sexy!
posted by jgirl at 10:13 AM on February 7

Advise against attempting a pencil skirt. It won't stay up unless you get it tailored, and it is too restrictive. You'll be walking like you have a stick up your ass.

The sarong look is absolutely smashing on a guy of your build. Quality of fabric is key here. A simple solid with nice texture and heft that drapes will look great. No need to go for the beachy tropical look (unless you fancy it). Easy to make your own.

Have fun!
posted by nacho fries at 10:20 AM on February 7

I love the look of what's being described here as a cargo skirt. A friend has one in black, that he wears with serious tall boots, and it looks great. If you're not used to wearing skirts, something more A-line or flared than pencil shape may be easier to deal with.

Tights: a standard drag queen tactic is to wear a pair of dark or flesh-toned solid tights, and then a pair of bright fishnets or other open patterned tights over them.

Also: please report back with pics!
posted by gingerbeer at 10:38 AM on February 7

Hi Ominous Paws! Try Primark with all these recommendations, they will have sizes to fit you, then buy a bunch of skirts and return the ones you don't want.
posted by ellieBOA at 10:59 AM on February 7

I wear unshaven legs with tights all the time (that's what winter is FOR!) and I find that once the leg hair reaches a certain length, it doesn't poke out much. So if you're currently all-natural, opaque tights darker than the color of your leg hair should work fine. If you're in between sizes, go bigger. Pantyhose-type tights will not cover leg hair. Dark lacy or fine fishnet tights might do the trick depending on how hairy you are.

I don't recommend a pencil skirt because they tend to really work the hip-to-waist ratio, which you probably don't have, and they can be very restrictive. That is not the skirt to wear on your first night in a skirt! I feel like you could go a lot shorter than those Marc Jacob looks.

But seriously, try some stuff on, it's hard to know what you will like in a type of clothing you've never worn before.
posted by mskyle at 11:33 AM on February 7

A local Zürich designer makes skirts specifically for men: Amok. They have an online shop (see the link), but I don't know about their shipping arrangements.
posted by FrereKhan at 11:49 AM on February 7

If you go with the sarong or one of the longer-style pleated skirts, match it with a pair of Docs or other classic combat-style boot. It gives you that masculine/feminine ambiguity, and it's also a very '90s look (which is super in right now).
posted by TheWhiteSkull at 12:09 PM on February 7

Assuming you'll be in a climate-controlled indoor setting (vs. outdoors freezing your budgies off), don't fuss with wearing hosiery.

Part of the joy of skirt-wearing is having your gams and nether regions moving freely and airly, skirt fabric caressing leg and loin.
posted by nacho fries at 12:36 PM on February 7

Most of the guys I know who wear skirts regularly are contra dancers, and wear calf- or ankle-length twirly cotton skirts (so that it twirls out when you spin around!). They go with any sort of casual shoes, from oxfords to hiking boots, and just regular socks. A t-shirt and either plaid flannel shirt or old cotton or wool sweater usually fits the skirt style. You can search for contra dancing videos on youtube or something to see examples. This may be more casual/hippy of a look than you are seeking, but for what it's worth, it's a look that seems to suit quite a variety of body types of men.
posted by eviemath at 1:58 PM on February 7

I don't know how it works on your side of the pond, but I find that another benefit of the more casual look is that second-hand/recycled funky clothing stores seem to be more open and less judgey about their patrons' purchases.
posted by eviemath at 2:01 PM on February 7

I'm about your size and I used to wear skirts all the time that (IMO) were neither femme nor utilikilty. But I mostly had to make them myself out of old pants or get them handmade for me. How long to do you have.

This is me, for style and shape suggestion.

And this.

And this.

I seem to also have spent a lot of time lying on the grass at that time in my life.
posted by 256 at 2:01 PM on February 7 [3 favorites]

As mentioned above, the key to really rocking whatever skirt you choose will be to give it a test run beforehand if at all possible so you can get used to it and learn to move confidently in it. Skirts, particularly flared/fuller skirts, are much, much less constricting than trousers and you will likely feel very loose and free (this is the fun of skirts!) Wear it around the house if you can, practice sitting, standing, leaning, dancing, etc. That way you will be confident you won't be exposing more than you mean to.

Also, if you normally carry your wallet in a back pocket, be prepared: most skirts have either very tiny pockets or none at all (hence, the need for a purse.) You'll want to think about this as you make your fashion selections for the evening.
posted by oblique red at 2:30 PM on February 7

I really love those contrasting colour wedge inserts in the converted-from-pants skirts, 256. That is a fantastic way to make a skirt, and it looks great, too. And it has POCKETS, which is absolutely critical.

I don't suppose you have any sort of construction advice for those?
posted by seanmpuckett at 2:35 PM on February 7

If you google "jeans into skirt" you'll get lots of hits, seanmpuckett. It's kind of a DYI staple. If you have any sewing skills at all, it's really easy. And even if you don't, it's still not crazy hard. Here's one video.
posted by looli at 5:13 PM on February 7 [1 favorite]

Wear a manly kilt and then whip it off as a party trick to reveal the feminine skirt beneath
posted by Bwithh at 5:53 PM on February 7

What, all these mentions of sarongs for men and no link to that famous photo of David Beckham in a sarong? Note he was wearing trousers under it.

Here's more recent inspiration, Givenchy spring/summer 2013 (with a link to the runway photo gallery). Note how those man skirts also go with trousers.
posted by bitteschoen at 7:25 PM on February 7

As always, thanks everyone for a totally unexpected degree of help. You're all bloody wonderful.

In the end I couldn't make oxford street, so had to make do with a Top Shop section in a pretty fierce section of North London - who turned out to be incredibly lovely and helpful. Couldn't get my first two choices, but ended up with a flippy black skater skirt, worn with a black polka-dotted tee, chambray jacket, military-type boots and - though I'd initially wanted to rock the skirt/hairy legs combo - very thick tights, as Friday was *freezing* out. There aws a club photog and pics were take, but they've yet to be posted!

Incidentally - every other guy there wearing a skirt changed at the venue. I was apparently the only one to make the journey (an hour on public transport for me) skirted. Wimps.
posted by ominous_paws at 3:09 AM on February 11 [8 favorites]

So I guess it's too late to edit window all of the English abuse in my above comment. That's what you get for quickly bashing out three paras on casual transvestism while looking out for your boss over your shoulder. Sigh.
posted by ominous_paws at 5:55 AM on February 11 [2 favorites]