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Tim Hamilton Gear

While we all enjoy the air of privileged insouciance classic preppy gear can lend you, no one wants the stigma of sharing apparel with men so old they can no longer heft their own croquet mallets. For a progressive take on iconic prep, check out Tim Hamilton, whose spring line debuts this week at Bergdorf's.

TH grew up in Cedar Rapids, Iowa -- apparently, a place where the right clothes can make you feel like you're not stuck huffing paint in Cedar Rapids, Iowa. After stints at Ralph Lauren and J. Crew, the restless Rapidian launched his own collection: a look that's enamored of the classics, but won't give the impression that your family retains a lawyer specifically to deal with yachting-related manslaughter charges. The cut of the gear (denim, trousers, sport coats, ties, t-shirts, knits, sweaters, and outerwear) is fitted and less boxy than standard prep, but it also avoids Euro-skinnypantsness -- a fit so taut, it exposes your delicate urethra.

In addition to looking good, this line's also blessedly versatile. Though it's classy enough for a party thrown by the family that invented the Mutual Fund, it's still ballsy enough to wear into a bar without some ruffian beating the insouciance out of you with your own croquet mallet.