Best Skirts for Men


Thanks to Pinterest and Google, fashion is blurring the lines between his and hers at a record rate. Women are wearing oversized watches, men’s pants, shirts, hoodies, and even copying men’s underwear styles. But what happens if a man decides to press the line into skirts which are socially accepted in most developed countries as “women’s wear”?

First off, let’s set the record straight and say skirts have ALWAYS been men’s wear – women’s fashion just borrowed it for a little while. Second – they’ve done a damn fine job of feminizing them over the past 100 years while men have slunk back to a mono-style of dress code (pants or…pants). So if your a guy, who decides you want to wear a skirt – awesome…good luck finding anything in the men’s wear section of your local store. You’re going to have to get a little familiar with the women’s section and realize there is a difference in body shapes between the sexes.

As a person – you should always feel you can wear anything – including clothing that is silky, short, pink, blue – whatever – it doesn’t matter if it feels good to you, but if you want to look and feel masculine in a skirt, there are a few does and don’ts that I’ve personally learned over the past five years that change the “uneasy” feeling around other men to a more, “that’s awesome” with open discussion.

Pick an “A” Frame Skirt

Think of a gladiator or a traditional Scottish kilt – Wide at the bottom, narrow in the waist. Because men typically have broad shoulders, wearing this style has a tendency to make you look anchored and well proportioned from top to bottom. Avoid pencil skirts and anything that is straight or skin tight – that style works for women with hips – but on a man with shoulders and tiny hips, you may end up looking like a tree getting felled that’s ready to topple over.

Knees or to the Floor

Mini skirts may look good on teenage girls, but they push the social comfort zone on a middle-aged man’s body. 3/4 skirts that end at the calf work if you have tall lace-up boots, but tend to look funny with any other kind of footwear. “Cankles” aren’t really trendy. The purpose of 3/4 length skirts should be to show off the appropriate footwear. That leaves us with knee length or to the floor. I live in Saskatchewan where it’s +30 C in the summer and -30 C in the winter. I wear skirts 7 days a week, 365 and both styles work for my climate. (yep, that’s me in the photos below).

Pockets, Zippers, Chains, Grommets, Belt Loops

Any hardware helps to “industrialize” the look. Most women’s skirts have tiny little pockets that can’t hold spare change or fake sewn pockets, so if you can find a garment that has actual deep pockets – bonus! Chains tend to scream Goth, but having a skirt with zippers or reinforcing grommets can help “man it up” a bit as opposed to a skirt that is stretchy or a tie-up style like a sarong.


Fabric and Colour

Denim, corduroy, heavy cotton blends, and wool in monotone, earthy colours work best for men. Try to avoid patterns or bright floral colours or skirts made from lightweight fabrics. Materials that are commonly used for “men’s” clothing help normalize the whole skirt wearing thing.


Final Words

I’m a 47-year-old male whose been wearing skirts publicly for about 5 years now. Happily married with two kids, skirts are just a norm for me and everyone who knows me. I, (like a lot of guys who want to wear a skirt or more feminine clothing), am typically drawn to clothing options that contradict what I say in this post. Please understand that I very freely wear silk wraps, floral skirts and share a wardrobe with my wife…but I’ve had five years to come into my own self-confidence and have learned how to deal with ignorant people in public settings. The heart of this post is to help anyone who is truly interested in pursuing wearing skirts for the first time and don’t want to rock the proverbial boat to the point of taking on water.

Regardless male, female, or gender-neutral – dress how you feel and whatever you decide – Own it! Let’s say, “Screw the gender-based clothing stores”, and make it a unisex world together!


3 thoughts on “Best Skirts for Men

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