I hope that when I'm in my fifties, I won't dress like I'm trying to be twenty-seven again. When I look at a guy in his fifties, nothing makes me think: tragic, as much as 1) Tight jeans - not even a good idea for young guys. 2) Anything that makes you look anything remotely like Kevin Costner, for that matter. 3) Anything overly trendy. Last weekend I saw a guy in his fifties at Neimans, could stand to lose a few pounds, wearing those painted Gucci jeans from a few seasons back. He had a rack of stuff that he wouldn't let anyone touch, and he was consulting with his wife, (girlfriend, stepdaughter?) I saw his picks, and I hope to god that he was either a fashion consultant for a boy band, or maybe Elton John, and that he wasn't shopping for himself. If he were my dad, I'd disown my family. 4) A continuation of number 3, this means stay away from any "edgy" designers and brands. Stick to classic designers and styles that will look pretty silly one season down the road. Your time for youthful indiscretion is over. 5) "European" style briefs swimsuits. Actually, a good rule for anyone not a professional swimmer. On the other hand, you might want to avoid looking prematurely eighty, so stay away from the preppy look (please god, don't ever follow Esquire's style advice) - you might even be able to avoid the "rich old guy I hate" look that invites angry youths to throw stones at your Mercedes. Don't say you haven't been warned.