Is Boring Style A Dating Dealbreaker?

Because I’m young and carefree, I’ve been keeping my options open and dating a couple of guys at the same time. No more than two, because beyond that, things get a little sloppy. Well, two works until decision time comes around and you’re writing out each one’s pros versus cons. That’s where I am right now — paper-ready,with pen in hand.

Guy #1 is nice, funny and cute, but Guy #2 is gloriously attractive and kind of witty. Sort of. Sometimes. OK, barely. The choice seems clear: ditch the hot, boring guy in favor of the cute, funny one, right? Not so fast. I thought I had arrived at that conclusion, but still haven’t actually axed Guy #2. My conundrum, after the jump …
I thought at first that the delay could be blamed on #2’s flaxen locks and 6’2″ stature — the perfect height in that it allows me to wear heels up to five inches without surpassing his height. I mean, that’s not the sort of thing a heel-loving gal like myself can easily shoot down. But the truth is, my hesitation has nothing to do with my style and everything to do with his competition’s.

Beyond a certain level of cleanliness and appearance maintenance — washing your face, brushing your hair, etc — people can’t really help their looks. But your style? That’s all a matter of choice. The fact is, Guy #2 has much better style than Guy #1. I know, this sounds terrible and you’re likely writing me off as a horrible person, but hear me out. Why shouldn’t someone’s style be a major factor in attraction and whether or not you continue to date him?

I am someone who is perpetually overdressed. I write about style and I love fashion. I appreciate clothing as an expression of who a person is. Guy #1, on the other hand, does not seem to have the same appreciation even in the slightest — he favors imagination-less t-shirts and shapeless jeans commonly worn by grade school boys. Though I am attracted to him, I am not attracted to his style. Help me out on this one: Is boring style a dealbreaker?