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

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.