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Can I Still Pull That Off?

A “Queer Eye” guide to dressing smartly at midlife

Alt text to come soon

There comes a time in every man’s life when he looks in his closet and asks himself, Can I still get away with this? The clothes he once wore with aplomb—leather pants, tank-top undershirts, skinny jeans, Dockers, jean shorts (do not call them jorts, thanks) — he wonders if he’s aged out of their “wear by” date. Are these fashion favorites still age-appropriate, or should they be retired?

I would contend that these are the wrong questions. Here are three things you should be asking instead.

Have I Earned This?

Lou Reed and Joey Ramone wore tight black pants to the very end. I’m 56, and you’ll have to pry my (genuine) CBGB T-shirt from my cold, dead body. I saw Soul Asylum and the Dandy Warhols there. I bought the shirt there. I earned that shirt.

If an item in your closet has a crazy story behind it, you’ve earned it, whether it’s a concert hoodie from a show you can barely remember or a “World’s Greatest Dad” tee.

Am I Being Authentic?

Why can Russell Brand, 46, get away with wearing scarves as a permanent fashion fixture, but Jared Leto, 49, wears one neck scarf this summer and he’s mocked mercilessly for his resemblance to Three's Company's Ralph Furley? Because Russell has been wearing scarves for longer than any of us have known his name—and for at least as long as he’s been forgetting to button his shirt.

The problems start when we try to change our look midstream. We don’t need to cut our pants 6 inches north of our shoes, as the millennials so adorably (and successfully) do. Nor is it likely to be a great idea at 40 to adopt their side-shaved, floppy-top hair.

But I work with a middle-aged guy who wears marching-band jackets on camera, and it totally works for him. (It would not for me.) Pharrell, 48, wears a Vivienne Westwood hat that would look ridiculous on anybody else. GQ once claimed that he “normalized weird fashion.” But it took almost a decade of his wearing this “weird fashion” before the press deemed it normal.

In other words, if it’s already in your closet, you have a constitutional right to rock it.

Who’s the Expert on Me?

Answer: You. For good reason, most clothing is not one size fits all. Its suitability in your sartorial life may depend on so many things: your line of work, your level of confidence, your personality, the place you live, your history and myriad other elements that can’t be quantified.

Trust your instincts and your own reflection in the mirror. Or consult your significant other, who has to be seen in your company now and then. At our age, we're dressing to please only two people: ourselves and our partners. As long as we're both happy, it's all good.

From left: Jeff Lipsky; Getty Images (4)