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How To Make Your Skirts Look Manly

Updated on October 16, 2009

Men who wear women's clothing in public are often struck with a particular challenge. How, in this pre fashion enlightened world, are they to wear their skirts out in public without having to go six rounds with the nearest moron. (Though, to be honest, depending on where you live, you may get nothing but smiles by going out in a dress.)

It is possible to be a guy, wear a skirt, and still look quite masculine. The advice in this article comes most entirely from my readers who actually go out there and wear skirts most days or every day. That's right, if you're sitting at home, wishing you had the courage to wear a skirt, take heart from the fact that there are plenty of men out there doing it already. Every man who takes a stand and wears a skirt represents one more step towards the great gender fashion wall coming down.

Remember too, you can always customize your skirts to your tastes. It's quite possible to look businesslike, formal and yes, masculine in a skirt.

Dave says: “As a guy I have worn a skirt exclusively for many years without any adverse responses. There aren't even any pants in my closet although there are plenty of pants in my wife's closet.... Start with a knee-length denim skirt with pockets, a front zipper & belt loops. Remember that skirts come in dozens of varieties. Since a skirt is a skirt by definition, don't waste your money on an impractical kilt type of a skirt that is heavy, uncomfortable & expensive to dry clean. I've bought most of my skirts for less than ten dollars.”

He also adds this parting shot, which I liked:

“You don't have to wear pants just because some idiot says that you have to wear them. Be a real man - make your own choices.”

Wizz says: “Cargo and denim are right on. One way to make it look more manish is to wrap an bush shirt bright coloured plaid say red and black squares, around your waist and tie the sleeves across your front. from the back it looks like you have tied a jersey or shirt around your waist if you contrast this with a say black skirt and red bush shirt it is a great tuff look.”

PatagoniaKid says: “Skirt recommendation: Try on a "Juniors Size" (hips fit men perfectly) Mini Cargo Skirt in place of shorts this summer. No modifications are necessary. These usually are worn on the hips like a good pair of jeans and are about as unisex as you can get. Costs are zip. Found some good camouflage cargo skirts on E-Bay for less then $2.00 and I treasure them! Also in Khaki or tan are great. Aeropostale, Nori, brands can be cheap with great quality. Search e-Bay for "Cargo mini skirt" and you will find some not all will look and fit a guy perfectly.

Length?? What to get.... Experience shows that a standard length mini skirt is 12" long (but they vary from 10.5" to 15"). The thing to realize as a guy is that a 12 inch mini is the same length as men’s GYM shorts so it really isn't a big transition from shorts! The word mini makes one think it is too short but it isn't. Reason for mid to upper thy skirts are mobility. You can move without the restriction a longer skirt has. (A micro mini usually less than 10.5" is about the same length as men’s running shorts).”

Do you have any additional tips? Add them in the comments!


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    • Skirted John profile image

      Skirted John 8 years ago from Seattle area, Washington

      Been a skirt wearer for 8 years. In my experience, I prefer to get away from legwear that goes over the knees. A pair of knee-high socks (or, sometimes even knee-high nylons) paired with a skirt, and normal shoes/boots is enough to make said skirt look manly enough. I only wear knee-length (and sometimes above-knee) skirts. I've tried longer skirts and don't care for them. Then again, I'm that guy who usually wears shorts in the dead of winter, just because I can, and don't care what others think. Plus, I find them warmer.

    • profile image

      tim kiltyman 8 years ago

      I'm sitting here wearing a kilted skirt, Why is it that mens skirts aren't more popular? Skirts are fine nothing wrong, now men need to look at the rest of our clothes,it makes the skirt stand out, get rid of the suit it does not fit in, the shirt next adapt so it has the look of a blouse but is still when you look a shirt. Then and only then will the skirt become a fashion choice for us.

    • profile image

      tim kiltyman 8 years ago

      A skirt yes enjoy wearing them, they are only clothes when it comes to it, or look at it this way.

      Skirts, the one legged trouser.

    • karlostheboy profile image

      karlostheboy 8 years ago from England

      Im a man in a skirt or kilt most of the time unless um working on my motorcycles or doing welding etc .I wear them as a man with my DM's I have many skirts made from reconstructed mens jeans .I have only ever had good remarks from female's .Men tend to look the other way I also find the teens of today are realy cool with the idea as my sons freinds tend to wear some form of make up and are always looking for new ways to be different. I live in the UK and find the skirt movement is slow never seing another man in a skirt while out skirted myself .Am I alone in the UK ?

    • profile image

      Mikk 8 years ago

      I've often found that most people disapprove and run people down in a shallow attempt to justify there own personal insecurities. Wear what you want and don't be afraid to be happy about it. Ignore those who would seek their happiness by destroying yours and go on and enjoy being you.

      Confidence is another factor that helps pull off the successful boy-in-a-dress look. If you wear something that makes you feel good about yourself you'll strike out into the world more confident and people generally take less notice or just won't care once they see how content you are with yourself. After all, a confident woman is more easy on the eyes and is accepted if she wears a dress or pants. There's no reason you can't wear a skirt and still hang on to your masculinity either (if thats what you're going for). Ever seen the movie Troy? Brad Pitt, along with other chunks of man-candy, pulls of a skirt in quite a masculine fashion, granted he is positively yummy while doing so, you don't have to be in olympic shape to wear one yourself.

    • Hope Alexander profile image

      Hope Alexander 8 years ago

      I wouldn't worry too much about the rigidity of people Mike, people like to make rules and boxes, it helps them feel safe. :)

    • profile image

      Mike 8 years ago

      I must be a rare duck -- I'm both types. I own a bunch of kilts and various manly skirts, which I wear without the slightest indication of being anything other than just a guy wearing a skirt. That's just me, dressing comfortably for the weather. Or maybe just to stand out from the crowd. Whatever.

      Other times, I like to do the full-on drag thing. And yeah, I look pretty good in a cocktail dress. :-)

      But it does seem as though there is very little overlap between the two camps. The men-in-skirts crowd thinks you've crossed a line if you shave your legs; the crossdresser crowd thinks it's heresy for a man to wear a skirt unless he's wearing that skirt with the right pair of pumps and a wig and makeup and fake boobs and-and-and has a name for some imaginary female persona that lives in his head (isn't that schizophrenia?) -- all because skirts are just for women!! Both are stupid. Why must everyone align themselves into such rigid sets of clothing dogma? I thought that's what we were supposed to be against! I've belonged to both kinds of forums, and found myself out of place in both.

    • profile image

      thatsnice 8 years ago


      I can understand your point of view however if I had the courage to wear a skirt in public I would certainly be sporting shaven legs and a pretty face (not outrageous... simply a little color), which is what I would truly want... Believe me, I go to work every day with a scruffy unshaven face and a very masculine attitude because I am required to do so to gain acceptance with my peers. I have been trapped in this situation since I was a child. Oh and I wouldn't need to be called Nancy... I adore James.. BTW Hope I stumbled across your articles this evening and am very inspired by your writing, I look forward to reading more!

    • perfumelover profile image

      perfumelover 8 years ago

      I love that you've put out a great debate here! I think that rocker skirt look you featured above is a great place to start--the kilt is timeless, ultimate masculine, and if we keep capitalizing on that history, I don't think we'd be stuck in a debate of the skirt being ultimately feminine or feminizing.

    • profile image

      Bobclops 8 years ago

      Dave is right on the button, The thought train is men in skirts, NOT men trying to look like women.

      When a woman puts on a pair of jeans, even if they are mans jeans, no body accuses her of crossdressing or getting in touch with her masculine side, so why are these assumptions applied to men?

    • Hope Alexander profile image

      Hope Alexander 8 years ago

      I do see your point Dave, I think there are really two groups of men interested in this issue.

      There are men who want to be able to retain their masculinity whilst wearing skirts and dresses, and then there are men who are more interested in expressing feminine elements.

      Both of these groups want to wear skirts and dresses (though for substantially different reasons,) and though I can appreciate the frustration of being confused with the second group when you are in the first, the second group nevertheless has the right to their preferences as well.

      I feel a hub coming on :)

    • profile image

      Dave 8 years ago


      My point in the first paragraph, albeit it judgmental, is that men who pretend to assume a feminine identity while wearing a skirt or a dress aren't contributing to the widespread acceptance of clothing choices for men on the same level than women today enjoy the freedom of choice regarding clothing. It is that the guy who assumes that he can pass as Nancy or Susan isn't being accepted by the general public as a man who just decided to wear a skirt rather than jeans on a particular day.

      Rephrased, a man wearing a skirt as a man is interpreted differently in my opinion than a man pretending to be a female while wearing a skirt.

      Sorry for not being more concise. Hope, your meeting place to share opinions here on the Internet is greatly appreciated.

    • Hope Alexander profile image

      Hope Alexander 8 years ago

      Dave, whilst you give some good tips here, I don't think the judgmental tone of your opening statements is overly helpful. If a guy wants to call himself Nancy or Susan, why shouldn't he? There are plenty of girls called Alex or Jack and nobody gives a rat's posterior.

    • profile image

      Dave 8 years ago

      Be a man & act like one. No wigs. No fake anything. Don't call yourself Nancy or Susan. When is the last time you saw a woman who stuffed socks into the front of her pants? All of this type of behavior is counter-productive.

      Plan your clothing for the task & the weather. A short pleated skirt on a windy day is not a good idea. A short skirt when you will be seated such as in a stadium is not a good idea. Forget roofing or climbing ladders. Common sense is always a good thing whether one is male or female. Listen to your wife's comments. She definitely knows a thing or two about skirts that you don't.

      See-through garments don't belong in the outside world.

      Get a full-length mirror & use it. No tags visible? Wear the garment correctly. The back of the skirt is not always so obvious. The zipper may be on the left side, the front or the back. Look for the tags. Check the mirror. Ask your spouse. Sure beats looking stupid.

      Get over the "kilt" fixation. Women aren't afraid of shopping in the men's, girl's or boy's department so why should we be. It's the fit & the style that matter. Ever seen a woman in men's board shorts? Of course you have. Don't call every skirt a kilt just because that will magically make it a "man's" garment. It won't. Get away from labels that are based on gender. It's the size & the fit that matter.

      Put the look together. Combat boots don't go with a tennis skirt. Colors & fabrics shouldn't clash. If you are color blind like me, ask your spouse.

      Get out there with pride. You don't need an excuse to wear anything that fits well & is appropriate for the task & the weather. Be your manly self & act like the real man that you are. Just do it.

    • Tomgeekery profile image

      Tomgeekery 8 years ago

      My experience is that people are too polite to even comment. I get some looks, but they are usually fleeting for the same reason. Most of the time I'm not even sure I didn't imagine it.

      If you happen to be near a beach a sarong is unlikely to draw attention. As an added bonus, it's an excellent way to wear bright colours.

      But my best advice is simply to go do it. Wear something you like the look of out in a public place, and act just as you normally would. The more you do, the easier it will get.

    • profile image

      kidme 8 years ago

      Pair it with a men's shirt.

      Avoid going commando when wearing a skirt. We don't want anything sticking out. That will freak others out more!


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