Don’t be that guy: Avoiding over-40 style pitfalls

GOOD OLD BOYS | From left: Both Brad Pitt, 53, and Steve Carell, 54, know how to nod to fashion without looking conspicuously “fashionable.” /PHOTO: GETTY IMAGES

By Terrance Flynn | The Wall Street Journal

ALL IT GUTSY or foolish, but as a younger man I was prone to taking the occasional fashion risk. When I was 30, for example, a pair of black leather pants spoke to me. I mean they actually made a sound when I pulled them on in the dressing room, that satisfying twisting noise of leather in motion. They also smelled like a catcher’s mitt and bulked up my thighs so that walking in them was a minor undertaking. But dressing outside my comfort zone had the pleasant effect of estranging me slightly from myself, of magnifying my boldness. (Then again, I bought the pants at Gap, the daring purveyor of the Pocket-T. So not all that risky.)

Ten years later, I was still at it. At 40, I fell prey to that illusion, perpetuated briefly in the aughts, that urban western wear was not as embarrassing as previously thought, and got myself a blue straw cowboy hat. I promptly took the hat on a weekend to Montauk—a trip whose sole purpose was to introduce me to the best friends of my new significant other. The relationship lasted a long time but so did the story of my appearing poolside, mounting a lounge chair like a saddle and donning that stupid hat as if to say: No big deal, I’m just wearing a blue cowboy hat at the pool—why wouldn’t I?

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