It'll be the hot-looking guy, unless you're wearing something really interesting. However, I'd be more likely to start a conversation with the average looking guy with the hot dress sense, if he's friendly. Gives us more to discuss and it's not as intimidating, if truth be told.
I don't care about the clothes. He could wear jeans & a Tshirt, and I'd be fine with that. Looks don't matter to me either cause an average looking guy with a great personality will be hot in my eyes. But given the two choices, I would choose the hot guy (providing that the two had equal personalties)
Either... I like fashion, I think guys in tuxes are hot... but I love how guys look in jeans and a tshirt... I'd take an average guy who dresses like an average person... but I believe in dressing for what your doing, so don't go to a nice party in average jeans and tshirt & don't hike a mountain in nice pants.
The hot guy. I am a girl who is a fanatic about fashion. Looking good and classy is a must. Average looking doesn't cut it. Someone's wardrobe can always change, so I see it as not only is he hot but I can help him shop. Which I love to do anyway!
You shouldn't hide behind your clothes. If there's anything about your character or your life that is making you insecure about your chances with women, work on fixing that. Throwing down money for a good outfit won't cut it. I rarely remember what people wear anyway.