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.

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8 Fashion Mistakes to Avoid

by Michael on January 18, 2010 · 0 comments

Apparently there's a drug dealer nearby. (Photo by Hauggen)

Men struggle with fashion. That’s a plain fact you can prove for yourself just by going to a sports bar. But with some simple guidelines we can all dress better and maybe attract a few more women in the process.

I’m not talking about something like 12 mistakes men make when dressing. When women write these things they get caught up in the minutiae that women may understand, but complaints like “too many fabrics” and “length of t-shirt” are a little fine for many of us to really absorb (unless you’re wearing a belly-t-shirt, dude — that’s just wrong).

No, when an average kind of guy writes a piece like this it turns out more like Asylum’s Top 8 Men’s Fashion Mistakes to Avoid, by Brad Adam, who for the most part nails it:

  • Worrying too much about what your buddies will think. This is usually an excuse for dressing down rather than dressing up. Just worry about looking good and let your buddies catch up, which they’ll do sometime around the third girl who flirts with you.
  • Not spending where it counts. Find some really nice basic pieces, and spend most of your fashion dollars there. You can wear an awesome jacket with a $8 t-shirt and look great, but the reverse is almost never true. I do differ from Brad here: if you don’t wear a watch in the first place, don’t start just for fashion. But if you’re wearing a plastic digital impulse buy from the drug store, then yeah, upgrade.
  • Wearing a dark dress shirt with a suit. This is close to cutting it fine, but dark-on-dark is advanced fashion and even some celebrities do it wrong.
  • Wearing dirty clothes. You know that “dot” of dried chili sauce on the pocket that you can “barely see”? Everyone sees it, they’re just too polite to mention it. And Brad didn’t mention the smell factor: even a clean-looking shirt shouldn’t be worn in public if you had to run 10 blocks to the bus last time you wore it.
  • Wearing clothes that are too large. At best, you’ll look 20 years out of date. At worst, your friends will ask when you’re due.
  • Mistaking expensive clothes for good-looking clothes. The Ed Hardy t-shirt era ended when Jon Gosselin started showing up in tabloids wearing them. Instead, find something cool at BustedTees, or better yet, a nice-fitting solid colored t-shirt and save yourself money and your friends nausea.
  • Trying to be too fashion-forward. You know what the new thing is? Skirts for men. That ought to keep you from straying far.
  • Not dressing to the occasion. Again, find a look that works for you, but also remember to adapt to the situation. Jeans to a funeral are always wrong, even if they’re black jeans.

The list could go farther, including “Being a mortal enemy of the ironing board” and “Wearing anything with ‘TapouT’ or ‘Affliction’ written on it” but we’ll let it rest there for now. Now I have to go purge my memory of Jon Gosselin again. With hard liquor.

Top 8 Men’s Fashion Mistakes to Avoid [Asylum]

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Sites to See: Men’s Underwear Blog

December 15, 2009 Dressing

Underwear is important. If you’ve read my guide to all things boxer and brief but you’re looking for a wider selection, you might want to try the Men’s Underwear Blog. From jockstraps to long johns, MUB keeps tabs on the manufacturers, styles and stores who offer a dizzying array of cuts, colors and patterns. Word […]

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Hump-Day Links X

August 19, 2009 Dressing

Happy Wednesday! I was going to include more on fashion, but the press has all decided to take a break in order to laugh at that Harvard stuff. Not that there isn’t a boatload of fun and education available out there: From the “Duh” Desk: Do Single Women Seek Attached Men? is about a study […]

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