Check out the
A50s from astrogaming.com [I realize that they're a bit more than $250] but they're considered the best on the market for gaming. I own a pair of the A40s myself for just over a year and they're amazing. Just as good as the day I bought them. Rich sound, great bass, 7.1 Dolby, 5.4GHz wireless, comfortable and sexy as hell.
You can rock them without a mic, if you choose, but they have an excellent mic as far as any gaming headsets go. I actually just put a pair up for sale [only to upgrade to A50s] but am considering a change of scenery for my battlestation and decided to keep them for now. They are, by far, the best headset I have owned. I have been through Razer, Turtle Beach, Steelseries and Tritons. None of them hold a flame to Astros in my opinion. Let's just say I won't consider another brand at this point
Now for your main concern; comfort. I have worn them for more than 24 hours straight during a few LANs with nothing but comfort, and that's with wearing eyeglasses. Eyeglasses tend to be the Achilles heel when it comes to gaming headsets and their comfort. If it passes the eyeglass test there's not much more you could ask for.
Anyway, that's my two cents. Hope it helps.