dreamLRG,
I have the following 3 headphones that I absolutely recommend:
Grado SR80i or Alessandro MS1 $99
Clarity: check
Good bass response: check
Stylish: check (this is personal since I think all Grado look cool, except the iGrado)
Comfort: check (the comfy pads are exactly what they claim to be, very comfy, and warm too, make great earmuffs)
AKG K701 somewhere around $200 for second hand, $300 for new
Clarity: check (crystal crystal crystal clear)
Good bass response: check (leaner bass than the Grado, but if you're not a basshead then you don't need to worry)
Stylish: big check (this is the reason I got them, white and red leather, best looker in AKG lineup)
Comfort: check (I wear these to watch movie after movie)
AKG K242 somewhere around $200-$250 new
Clarity: check (slight darker sound that the Grado and the K701, not piercing and crystal clear, but because of this you can listen for hours without treble fatigue)
Good bass response: big check (nice full bass here, but not overwhelming, which is a good thing)
Stylish: check (only if you like the retro look)
Comfort: big check (very light headphones)
You have a big head??? Oh crap, I have a small head, but still....try with confidence