From time to time, men are tempted to take a chance with fashion. Recently political commentator Roland Martin did just that, wearing an ascot on his CNN program. The result was a swift mocking by Jon Stewart:
And with good reason: we tend to see a man in an ascot as less authoritative. It’s considered casual wear, or worse, affectation.
But in the world of TV opinion, up is down and dogs are cats, so Martin had a very good reason for sporting his fancy neckwear, which he went on about for, oh, a good three minutes:
In case you don’t want to bother, or can’t stomach today’s political commentary, he essentially said he’s wearing ascots because America’s founding fathers did. To which I say, when he starts wearing the powdered wig and leggings as well, I’ll consider him authentic.
But there’s a lesson to be learned here all the same: Martin’s ability to “pull off” the ascot is diminished by his justification. If he simply said, “I look better in this than I do in a necktie,” we might take him more seriously. As it stands, it makes him even more of a cartoon character. Wearing colors like metallic gold doesn’t help either. Of course, it gets him noticed, and in his profession getting noticed is half the battle. But when you consider wearing something risky to stand out, think about the price you’re paying to draw attention.
Other risky choices may or may not be you. Will a fuzzy pimp hat really get you laid? Perhaps, in just the right context. “Mystery” rocked the fuzzy pimp hat in his life as a pickup artist, and it can’t be argued that he developed a way with women. But remember that the method he and Neil “Style” Strauss were using to pick up girls in the early ’00s involved basically posing as rock stars, with a mansion in the hills to back it up.
The best path to taking fashion risks is to try something just a step beyond what you wear now. One of the best “risks” I’ve taken was to top my look with a velvet blazer. At one point I had one in black, one with light pinstripes and one in deep red. The reason they worked was that at first glance I would look more well-dressed than the vast majority of guys in the room, and then when I got closer the natural instinct most women would have was to touch my jacket. It worked like a sartorial wingman.
Some guys might get mileage out of a pair of great shoes (I do that too). Others might look great in a porkpie hat (makes a great prop for “locking in” a girl you like when you have her wear it). Still others might be better off with a modern-preppy look. Try some things, and see what works. Have a female friend come along if possible.
The point here is that you shouldn’t have to justify risks or become a cartoon character—”It looks good” should be all the reason you need.