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Men, What’s Keeping You from Dressing Like This?

by Alex John |

If you haven’t seen the meme asking this very question, these words always accompany a man dressing unusually. Like all memes, it started with a sincere question by someone who was probably a little out of touch. With constantly changing standards on what “dressing like a man” really means, it’s easy to find yourself out of touch. That is, of course, until you allow yourself the freedom to realize that, if you’re a man, whatever you choose is what a man would wear. Here are some fun ways to mix it up and discover what you truly love.


Not only are heels of all kinds coming back in to men’s fashion this year, but used in conjunction with the right piece, they can be a regular feature of any man’s wardrobe. It’s power move to put yourself on a little platform, sure, but it also makes your calves pop and gives you a toned look without having to look too swole.

Big Hats

Remember that trend a few years back with the trilby hat? You probably saw it called a “fedora,” but this tiny almost-fedora never-was, yet had a life exceeding its moment in the spotlight because of people who substituted a hat for a personality. Big hats, though? That’s what the small-hat people were afraid to commit to. Go for a real fedora, or a Stetson – it draws attention and lets you hide at the same time.


Before you skip ahead out of fear, consider that men have been wearing dresses forever. It’s only in the last century that this has changed, much, and in certain places of the world, it’s still commonplace. It’s like the whole “blue is masculine, pink is feminine” myth – 100 years ago, it was the exact opposite. And why? Same as now – people just agreed it was the way to go. Fun thing is, you’re also allowed to show off your legs and feel the free breeze. Even if you just start at a kilt, you’ll know exactly why a skirt can suit anybody.


Men can get afraid of color. Not one color – usually most men find themselves allowing a single motif into a nice outfit – but all the colors. We’re talking psychedelic dream Punky Brewster stuff. There’s only one way to find what you like – experiment! Throw a bunch of stuff together, wear it with confidence regardless of what you think at first, and see how you feel as your pretending not to care becomes less and less of an act. Live it up.

In Clothesing

Don’t tether yourself to what other people think of you. Being a man is just… being a person. Be your truest self and find a way, through clothes and other means, of expressing who that person is, what that person wants, and how they want to live their life. Trying something new can be scary, energizing and fun – and doing this with clothes is a great first step.