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Daring Dresses and Skirts For Men

Updated on October 13, 2009

Wearing a dress when you're a man is always something of a daring proposition. How will you be received by those around you? I believe it very much depends on several factors, including where you live, what you're hoping to achieve with your look and how you carry yourself. I also believe that it is quite possible for a man to wear a dress and look incredibly good doing it.

There are two totally different ways for a man to wear a dress. Neither one is better than the other, but they must be understood as being different none the less. Some men wear dresses because they like the style. They want to appear masculine whilst enjoying wearing a dress. Other men wear dresses because they want to be feminine.

This particular article is aimed at the first group, because there is so little written for them and because they are forever being lumped into the feminine cross dresser category, much to their chagrin. As is well known now, I have a soft spot for feminine cross dressers, but nothing is more sexy than a masculine man in a dress. American author Susan Sontag, said it best when she said:

What is most beautiful in virile men is something feminine; what is most beautiful in feminine women is something masculine.”

Interestingly, Susan herself was a woman with very strong features, there was a touch of the masculine about her and she was absolutely gorgeous. I think that although men who want to wear dresses purely because they like the style may not wish to evoke a feminine image, they have to realize that they will inevitably do so. Fortunately this is not at all a bad thing. Black text is most visible against a white background, and masculinity is never quite so heightened as when it is portrayed with a hint of contrasting femininity.

Skirts and dresses can both be worn by men, though most men will find that skirts are easier to find in sizes and styles that both flatter and fit. From long skirts which create dramatic straight lines, to shorter skirts which make the summer heat comfortable, men really can take advantage of women's fashions without having to worry about re-styling them for their purposes. Generally speaking, as long as the skirt has enough room in it for a man to take a decent stride, he is going to look quite masculine in it.

So if you're a man who wants to wear a skirt, don't wait another day, there are plenty of guys out there already rocking their skirts and though some women may protest, there are many more who absolutely love it.


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    • profile image


      8 years ago

      Wear your skirt out in public. If you feel good and look confident, you will notice that people really "don't" notice.If you look sheepish, unsure and uncomfortable. You will draw attention to yourself for all the wrong reasons. Walk like you own the street and you have every right to wear whay you like. You do have that right! You'll soon find that if anyone does stare for a little longer than usual, you should make eye contact with them. They will either look away, embarrassed, or simply give a knowing smile or give nod in admiration of your confidence, OR balls.It's usually the latter. It may take time to master this, but when you do, the feeling of empowerment is overwhelming. I personally find dresses not to my liking, but that's because they tend to be made for the female frame and are a little too feminine. Design one for men and I'll try one. I know Midas clothing do one.I don't like them though. My wife loves my choice of skirts and outfits and likes it when I choose her outfits for her. As skirt wearing men, we need to mix and match. Using our imagination, keeps styles fresh and trendy, maybe even 'Anti-fasion'. I was wondering if wearing a skirt is fasionable(as in fresh off the catwalk), or 'anti-fasion'. There's another subject. I am straight and have a child. Even my conseravative in-laws accept it. "Dare to wear"!

    • profile image


      8 years ago

      Skorts and kilts work for me...

    • profile image


      8 years ago

      I think the guy in the first pic looks just fine!

      For myself, I like cargo skirts, I don't see myself ever happily getting to a pocket free existence. I recently got a "city safari" camo one that is near perfect for a guy. I recommend them highly! I also have found some shorter kilt/skirts I'm considering getting, but they lack pockets of any sort, sadly.I also find sports skirts, say 15", pull on, made of nylon/spandex are great to knock around the house in. I got into those as an aftershower wear at first, and then realized how nice they were to wear. These hubs are getting read, I hope Hope keeps up the great work. I'd really like to see skirts on guys as guys get more accepted here in the western world.

      Personally, I like short skirts, around 15-17", that can provide easy movement as I am active. I've got strong legs and I'm lucky to be slim. I'm crossing my fingers that this kind of thing takes hold in fashion.

    • profile image


      9 years ago

      I believe that many men just wearing skirts at home, and do not talk about with friends, colleagues etc.

      There is nothing wrong with wearing a skirt or dress, it is the original kind of men's wardrobe anyway.

      Don't be afraid to go in public with your skirts, you'll learn pretty fast that most people will like that - and give you a lot of compliments. I have experience.

    • profile image


      9 years ago from

      David H. said: I think most males who wear skirts dress in a feminine manner, because they are afraid to wear it as a man.

      Maybe, but there are at least 2 web sites that have scads of manly men who wear skirts and some dresses in completely masculine looks.

      These sites are and Both of these sites have at least 50 manly men who want to and do wear skirts and or dresses in a masculine manly way. Come check them out. You may be surprised on how many there are and their outlooks on "skirts for men".

    • profile image

      Joe S 

      9 years ago

      I enjoy weaing a skirt or a kilt. I just played two rounds of golf in Florida wearing a kilt and I enjoyed the exerience. I also wore a blue denim skirt to Walmart and Saw Grass Mills shopping center and no one really noticed or cared. Just do it-I will from now on. I just like the style and comfort.

    • karlostheboy profile image


      9 years ago from England

      Skirts for men worn as a man is how I see it I enjoy the freedom of movement and the freshness a skirt gives. In the summer I’m always in a skirt or kilt my favourite is my denim cargo skirt with a camouflage vest and walking boots I can tell you there’s nothing feminine about that setup .The only thing is I’ve never on all my outings come across another man in a skirt so I must assume I’m the only man in the UK who actually goes out in a skirt????

    • profile image


      9 years ago

      I have restrained my skirt wearing a little lately. One of my favourites is an ankle-length denim skirt given to me by my wife when we both lost weight.

      Most mornings I wear a 'swim skirt' bought for US$10 to US$14 on sale at L.L.Bean. The very short skirt is really comfortable. Dressed up a bit it also seems appropriate when I'm cleaning the bathroom on my wife's medication day (It's one that prevents her stooping for some time).

    • Hope Alexander profile imageAUTHOR

      Hope Alexander 

      9 years ago

      Good for you, Nanciboy! It really is quite possible for men to integrate feminine fashions into their everyday wear without raising a riot, it seems :)

    • profile image


      9 years ago

      I wore two full, knee length cotton skirts (at different times of course) on my trip to visit my parents and friends two weeks ago. Nothing beats a skirt for comfort when you are driving 700 miles in the late summer heat.

      My parents are 89 and conservative and don't need to deal with their son wearing "women's" clothing. But I wore a pair of crop pants and sandals showing my red pedicure to my friends. They made no comment about that so next year it will be a skirt.

      I wear skirts around my apartment building all the time and was seen by two of my neighbors in the last week with no problems or comments. I also occasionally wear skirts on the streets of San Francisco, again without problems. When I do I probably present somewhere between masculine and feminine. A skirt, women's sandals and pedicure on the bottom and a woman's but not overly feminine top. And a hat to cover my bald head. :)

    • profile image


      9 years ago from Central Coast NSW Australia

      I have a couple of dresses and skirts that unfortunately, only get to wear when my wife is not here but just love them on.

      So easy and nonrestrictive, they are are the perfect article of clothing for men.

      I keep hoping for the day when they become a regular part of a mans wardrobe.

      The question of do i wear it as as a man or a CD? It depends on the day as to how i feel.

    • profile image


      9 years ago

      I like that quote by Susan Sontag. One of the things that attracted me to women's clothing was the availibility of elastic waist pants. I also like the softer lighter materials and the jersey knits are awesome. To me, there's nothing better than a great pair of black wide-leg pants and a comfortable knit tunic top. Although I don't wear skirts personally, they would seem to be a very comfortable alternative to pants and I have to say they look very nice on the gentlemen above. Hmmm... maybe I just talked myself into trying a skirt!

    • David H profile image

      David H 

      9 years ago from England

      I can not disagree with you, as I have worn skirts in male mode during the summer to one of my jobs. No comments (either negative or positive) or strange looks at all. In fact, I am treated the same as if I wear trousers.

      I am able to do this because I see nothing wrong with it.

      Until someone explains why men can not wear skirts, then I will continue to do so. So far, not a single person in the Western World has come up with a suitable answer.

      If other men wish to wear a skirt, then all I ask for is a bit of decency - not showing anything which may upset others. I think knee-length or longer is appropriate.

      Some see this as crossdressing. Well, women who wear trousers MUST BE crossdressers too. See how ridiculous this sounds?

      I think most males who wear skirts dress in a feminine manner, because they are afraid to wear it as a man.

      What is there to be scared of? A piece of cotton? lol

      Maybe I have more courage then the rest of these macho guys put together!!

      Personally I prefer everyone (even women) to wear skirts rather than dresses. I just prefer the style of seperates.

      Of course, it is down to each individual though.

    • profile image


      9 years ago

      great hub i love to wear a dress now and then but as you say there are not that many that will fit straight off the peg, i have a nice denim "jumper" (wat the americans call a dress with no arms) which i wear with either a t shirt under or with a nice blouse under.

      as you said it is much easyer to get a skirt to fit men than to get a dress as most of us men have no boobs and look funny unless we are transvestites trying to pass as a woman when wearing a dress it is time for the designers to start making dresses and skirts in male fits when people start to see them in the mens section then it will be accepted for men to wear them with no trouble.

      again a great hub hope many thanks


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