I once dated a guy who clothed himself almost exclusively in band t-shirts, pleated trousers, and an ever-present fanny pack. (And no, he wasn't a German tourist.) I remember thinking when we met that I'd finally cast eyes upon the archetypal rock critic. That he actually was a rock critic made the experience all the richer. Because he was smart, funny and cute-ish, I chose to overlook his sartorial missteps and we quickly fell in love. But despite my best efforts—including renaming the fanny pack his "colostomy bag"—I never could convince him to spiff up.
LA-based stylist and personal shopper Eleanor Estes says there are two types of men: "They either have a well-thought-out style or they're clueless and malleable." Though his look was hideous, my long-ago ex was the former. "Men collect free t-shirts, no matter how hideous they are!" Estes says, sympathetically. The Frisky: After You've Googled Your Date, Check Out His Persona
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"Wait, how did you know they were free?" I ask. Estes laughs. "Men think free t-shirts are the most amazing thing ever only because they're free—there's no other criteria!" Her advice for getting rid of the hole-peppered Residents shirt: Don't. "The specific items that I don't like, I keep at the bottom of the laundry hamper—I get it out of the mix, without throwing it out."
She also suggests buying replacement items so you can rotate the offensive pieces out. "Respond positively when they're wearing something you like and just don't say anything at all when they're wearing something you hate."
Cindy Wheeler, owner of Brooklyn's hipster clothing mecca, Beacon's Closet, sees loads of couples shopping together and agrees with Estes. "Men take their choices so personally; it's very delicate. A better idea than saying 'that shirt is awful' is replacing it with something that looks good. And then when they put that on, accentuate the positive."
So basically, calling his fanny pack a colostomy bag was a bad idea. The Frisky: Guys Have Insecurities, Just Like Women!
My friend Becky successfully made over a long-term boyfriend by using positive reinforcement. "He was a great guy—I loved his heart and soul but not his style," she tells me. "He had a cheesy perm and used to wear cardigans tied over his shoulders with Pink polo shirts." While the two were in Spain, Becky convinced him to spring for a custom pair of black leather jeans.
Soon, instead of wearing preppy pink polos, her man was stomping around in motorcycle boots and close-cropped hair. While he looked about a thousand times better, Becky's story does not have a happy ending. "I made him too cool and attractive to other women," she laments. "So when we moved to his home city of Tokyo, all the women in his office hit on him and he wound up having an affair with the receptionist." Ladies, be careful what you wish for.