It is the 2009 fall season, you wear $300 destroyed Japanese selvedge jeans, a buttoned-up chambray shirt, constructed –one size too small– herringbone jacket, vintage hat, distressed work boots, and didn't shave in three days: you are "IN", but if you are caught wearing the same outfit in 1929 you would only be taken for an ex-convict or a hobo, or both.
Now imagine yourself wearing 70's low hip bell-bottom pants and a poly-cotton t-shirt with some faded graphic like Charlie's Angels, Atari, Seven Up or John Deere's logo... in 1995! Do you think you are five years ahead of the curve? Will your friends think you are original or inventive? A trend-setter? No, you just look weird and maybe stupid.
2007, you wear a tight suit with a narrow lapel, one inch tie and slim pants showing two inches of socks (even better sans socks), you are cool, but if you do that in the 80's, you are Pee Wee Herman, and look funny... and pathetic. If you dress like the 80's in the 90's, you don't get it, if you do it in 2009, you do. (Remember those awful oversized glasses, shapped like old tv screens, that touched your cheeks when you smiled, they have been back for a while, as well as the gaudy sneakers with velcro in the ankles, the colorful leggings, the t-shirt dress, the silver leather belt... go figure skating!)
I like to think I am open minded in general, but there are things in fashion that still puzzle me. For example I'm not sure where "saggin' pants" falls, is it still "IN" or already "OUT"? What I know is that wearing jeans below your cheeks is not very practical, at least for the real thugs: not long ago a suspect on the run trampled on his own pants when these dropped to his knees, with the result of being caught by the police after being shot in the rear. The cops, the paramedics, the judge, the jury, even the fellow inmates in his prison block, are still laughing, understandably.
Being fashionable is all about timing. But if you are like me, the kind of person that is never sure when to clap at a classical music concert, maybe it's better if you give up trying to set trends too early or with references so obscure that nobody can actually place them. Stop trying to be creative and go with the wave. Keep and ear and and eye open and wear the fashionable clothing when it hits the stores, still warm from the factories of China. Be an enthusiastic early adopter. People will recognize and admire your fashion sense.
There is a fine line between being a trendsetter and looking plain silly, stay on it, like a tightroper of style.