MainStreet.com has come out with a list of "Drinks Guys Can Order and Not Feel Like Wusses." I usually hate this kind of list, but this one seems to be starting from a relatively solid point -- Rusty Nail, check, Manhattan, check, Old-Fashioned, check, Caipirinha, check.
True to my highly-opinionated style, I've got some quibbles -- I'd say that's not enough vermouth in their Manhattan (I like 'em closer to 3:1 than 5:1) and I'm not a fan of blended Candian whiskies in general; actually, I'd go for a bourbon Manhattan before one made with Canadian. And soda doesn't belong anywhere near an Old-Fashioned, and a Caipirinha -- which is damn close to a Mojito -- really demands muddled lime. (...don't get me even started on the "Flaming Dr. Pepper".)
But really, a guy should be able to order anything he wants. (Likewise for distaff drinkers.) If a woman drinks Manhattans, that's frankly kind of cool in my book. And I've ordered Singapore Slings with no threat to my self-image. (And the Cosmopolitan -- a well-made one -- is a wonderful cocktail.)
Simply put, doing what you want and being true to yourself is what gets you the "style points", not worrying about how your choices are perceived. But if this gets someone to try a Manhattan or an Old-Fashioned on their next night out, so much the better. Go for a Sidecar the next time around, and you'll be a cocktailian in no time.