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How Men Can Wear Women's Clothing, But Still Look Masculine

Updated on January 1, 2010
The A Line Skirt Is Your Friend. This skirt comes from
The A Line Skirt Is Your Friend. This skirt comes from

This is a question from a reader, it's taken me three months to answer, mostly because I'm not very good at reading the little hidden questiony bits they have here. It's a very good question however, and it is most worthy of an answer.

The Question: You have some interesting pages such as power-skirts for men. Now I don't want to pretend to be a women, or pretend to be Scottish. How does someone pull off, for example a skirt, in the context of an otherwise complete manly outfit, especially with respect to shoes/boots, career wear, hose, body-hair, and I suppose underwear, just in case of strong wind?

The Answer: Most of this really comes down to your own personal sense of style, so take this with a pinch of 'just somebody's opinion' salt, but here's what I reckon when it comes to integrating a skirt into a male outfit.

First off, you have two separate challenges as I see it. You have your business outfit, and your casual outfit. Let's start with the business one first, as there's a greater than even chance you'll be spending 40 + hours a week trying to look professional.

For a business look, I reccomend a long, dark, A line skirt. An A-line skirt is one that starts at the waist, as they all do and flares straight down into an A-line, ie, the lines of the skirt flare out consistently on the way down, but not so much that you look like a fairy princess, and not so little that you're hobbled by the skirt. I'd avoid tight or fitting skirts designed to accentuate the butt and thighs, I'm personally of the opinion that very few women can really pull these off successfully, and though you should feel free to wear such a garment in your free time for a touch of glamour, highlighting your ass isn't exactly professional.

So, a nice, straight, long a line skirt that comes down no more or less than a couple of inches off the floor. Not so long that you will trip over it. Not so short that you will be exposing a great deal of ankle. I don't know why, but ankles seem to look awkward under long skirts, almost as if you belong to some sort of cult.

Underneath the skirt, some dark opaque stockings or pantyhose. This will ensure that if you do flash some skin, it won't be hairy leg, it will be smooth stocking.

Footwear wise, traditional business footwear will work well. Ensure that it is black or dark, not blue or brown. Up top, a neutral shirt and tie and, if necessary, dark blazer that matches the color of the skirt will create a seamless professional look that incorporates the skirt.

When it comes to casual attire, you can give yourself more free reign. Denims and more fanciful fabrics are appropriate for men, though if you do not wish to look feminine, I would keep the length of the skirt below the knee. There's just something about a shorter skirt that screams 'feminine', which is fine if you're looking for the feminine look, but not so much if you want to make a manly outfit. A loose denim skirt with a hooded sweatshirt and skate shoes will look fine on a man. Again, if you want to avoid the feminine look, stick with the A-line types of skirts, they allow a better range of movement than their more fitted cousins and they are less uber feminine, if you know what I mean.

Of course, it is important that you incorporate women's attire into the sort of clothing you already like to wear. It's usually quite easy to find women's skirts that will match men's tops, and if you really want to take things up a notch to the northern part of the body, men can usually wear a great deal of women's tops. T-shirts and tanks lend themselves to unisex wear quite well.

Have fun and play around with different styles and different kinds of clothing. Style and fashion are all about personal choice and in spite of what the snotty little fashion writers like to imagine, there's really no such thing as 'in' or 'out', if it compliments you, its in.


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    • profile image

      Thong  7 years ago

      Hey I am a young woman and I love that men want to wear womens clotihng. Way to bring change into the world on a positive note. I would love to see a fashion show where men are wearing womens clothes, give them abusive people something to think about.

    • profile image

      Doug 8 years ago

      In the summertime, for casual wear, men have a lot of options. There are a ton of skirts that are very similar to cargo shorts, and you can buy them anywhere. I like shopping at Old Navy in the States. I know that a lot of hub readers don’t like skorts, but there are some really cute ones designed for golf, if you want to branch out into bolder patterns. Denim, of course is always a safe choice. I recommend skirt lengths the same length as a pair of shorts you would wear in public. A lot of the time, people don’t even notice that your wearing a skirt at first glance. I do agree that in cooler weather, it’s better to wear something below the knee. Of course, my wife will challenge any claim I might make to having a sense of fashion!

    • profile image

      Doug 8 years ago

      I enjoy the feeling of wearing a straightline skirt which doesn't allow me to take a full stride. It reminds me that I'm not wearing pants, and personally, I like to let my feminine side shine sometimes. Also, I don't find myself climbing over railings on a regular basis anyway, so that's not really an issue.

    • profile image

      Doug 8 years ago

      For casual wear, I prefer a shorter skirt, one that is about the same length as a pair of hiking shorts. In fact, I like skirts that have the look of hiking shorts with pockets and solid, neutral colors.

      For the record, I have never received a single comment, positive or negative while wearing a skirt. However, I have gotten some very positive non-verbal reactions, as well as raised eyebrows, which I can live with.

    • profile image

      john 8 years ago

      I found this article very informative and useful, many thanks it will certainly help when I'm next shopping for a skirt or dress. And in case you're wondering my wife does know.

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      AMM 8 years ago

      a nice, straight, long a line skirt that comes down no

      more or less than a couple of inches off the floor.

      Not so long that you will trip over it. Not so short

      that you will be exposing a great deal of ankle.


      I find that "a couple of inches off the floor" is not enough to avoid stepping on the hem. Stairs, in particular are an issue, unless the hem is at least 9 inches off the floor. (Most building codes specify a rise of 7 inches for stairs.) Some have suggested just lifting up the skirt when going up or down stairs, but this is not only impractical if you're carrying something, but it doesn't exactly project a "masculine" image.

      One difference I've notice between men's and ("feminine") women's clothes is that the men's clothes don't restrict one's motion or activities (other than out of the desire not to stain one's $1,000 suit), whereas women's clothes often limit the wearer's activity: she may have to walk differently, or have trouble climbing stairs, or have to be careful how she sits or leans over.

      For instance, the skirt pictured in your article looks like it would limit one's stride and make it hard to, say, climb over a railing.

    • profile image

      SkirtedMan 8 years ago from

      I forgot to mention that in I'm "Since1982"

    • profile image

      SkirtedMan 8 years ago from

      Go to and access the forum "Pics and Looks" look under my name for a picture of me from the 2006 World Series of Poker in the Rio Hotel in Las Vegas. I'm wearing a pale blue T-shirt, a dark blue mid calf straight skirt, socks and brown loafer shoes. I'm also wearing a "Fanny Pack" in the front like a Scottish Sporran. I think I'm about as manly looking as one can be in a skirt and a T-shirt getting his picture taken by one of the courtesy suites "hottie" staff who had nothing but compliments for me because of my skirt. In pants, the only comments usually made to me are ones that are unfriendly because I'm overweight. In a skirt, no one notices the weight, just makes nice comments about a comfortable looking man in a skirt.

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      maninfl 8 years ago

      Hey guys, skirts are great. You're going to love them. I know it takes ba**s to wear one. Thing is if you do, what you will hear is compliments.

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      Mike 8 years ago

      "Hi Hope I long for the day when a man can wear a skirt as part of every day fashion and not be laughed at or abused for being different"


      I guess I'll just keep carrying the burden of being different until the timid souls catch up.

      Know what it takes to get the populace used to the idea of men wearing skirts? Men wearing skirts! Duh, right?

      You can either *be* the change in the world, or live in your self-made prison... but quit whining about it. The choice is yours. Nobody's got a gun to your head, forcing you to wear pants.

    • profile image 8 years ago


      I just found your post, let me tell you something: I just did it this new year eve: In Mexico city. Where most people goes great lenghts for not being taked as "gays"

      I bought an ankle lenght skirt on december 30th, especially for the following day party, it was a black one, I even try it at the store to have the right size. tip: always do this as with any other garmet, stop telling that is for your wife, sister or mother. Be bold and say: "may I use your dresser, it's for me and I want to look who does it fits on me"

      My skirt is the A cut that you mention, maybe slightly straight but looser at the bottom than at the waist. I liked that it was buttoned and has the zipper at the back, since it gaves you a clean style in front. It has a stitching over the front of each legs so it has some of the efect of a "pants creases"

      I wore it with formal shoes (male), a white shirt,ofxord gray pullover, and oxford gray long overcoat.

      We enjoyed a very nice party, danced and talked for hours and nobody seemed to care, as the combination expresed what it was: "an alternative to pants". Many people could no care less.

      The party was held at a public bar for everybody just to walk in and join. So i was not hidding at nmy place with only my friends or family

      The only thing I can say in this matter, stop asking for permition, just put the skirt on and go on with yoir life, that's how women started wearing pants.

      As for getting your first skirts: replace the pants, you don wear shorts for most of the places. dont you? you wear ankle lenght pants, so use an ankle lenght skirt. Be modest. Latter we can push for the shorter ones, but one step at the time.

      best wishes

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      8 years ago

      Thanks for spending three months on my question. It is highly appreciated.

      I actually débuted my first skirt outfit at a newyear party, and it totally worked, plus I had fun wearing it.

      2010 IS the year of the male skirt. Forget H&M's timid steps into male skirts. Raid the women's clothing department today.

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      likewhatiam 8 years ago

      Hi Hope I long for the day when a man can wear a skirt as part of every day fashion and not be laughed at or abused for being different it would sure be a happy day in my life.I would love to be able to wear stockings and suspenders as well under my skirts.Keep up the good work.

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      Cyndie_D 8 years ago

      Great advice, thanks Hope

    • Hope Alexander profile image

      Hope Alexander 8 years ago

      Men's skirts are coming in at the moment, as you'll probably be aware, H&M are running a line at the moment. It's a good time to get into skirt wearing if you've been thinking about it.

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      ILoveLingerie 8 years ago

      Those are some great tips, Hope!

      I like skirts, I only have one though at the moment, maybe I should expand in that field.