Coming from a guy with expensive taste, here's some life-lessons:
Designer jeans and clothing are not always better, but when they are, they are insurmountably better. I'm talking leaps and bounds. I too have cheap pants (work is dress casual, so I usually wear fitted jeans and dress shirts. A majority are from Express, lots are from H&M), and I go through them very quickly. You guys can blow smoke all you want, but $20 jeans will give you $20 value.
Knowing how to dress and present yourself does not make you gay, does not make you high maintenance, and does not make you better than anyone else. Style is personal preference. As far as I'm concerned, you guys can look however you want. Doesn't affect me in the slightest, and I don't care. Want to wear a backwards hat? Go ahead, it's your hat/head. I will, however, think "that hat would function better the way it was intended to be worn", but only in my head.
"Hair should be clean cut, and next to no maintenance" subjective statement here. I visit my barber once every two weeks, sometimes more. A clean hairline is a MUST. I do my hair every morning (takes me a whole of two minutes). While it's low maintenance, a "run a comb through it and go" style does not always work. It depends on the person and their style. Some dudes try to pull this off, and look like slopopotamus'.
As everyone has stated, confidence is key. If you're confident looking like a bum, I'm willing to bet you'll still pull chicks. Attitude and mindset radiate over clothing, material possessions, etc.
Sorry to threadjack, Tom, but had to drop my
in this b****. I'm by no means some pimp/ladies man. I'm comfortable with who I am. I'm older, and still coping with the fact that I can't run through hoes like I could before (I just don't have the desire), but I'm still confident in who I am, and don't give a s*** what others think (to an understandable extent
).