Sennheiser HD280s have a pleasant sound and are very comfy to wear for only ~$100.
Personally, I wouldn't spend $250 on monitoring headphones. No matter what headphones I produce on, I put the mix on speakers afterwards and find it to sound different from what I was expecting. Headphones are useful for being able to sit on the couch and lay down some drum and synth patterns in comfort, but for legitimate mixing purposes you can't tear me away from using speakers.
Therefore I wouldn't splurge on headphones; at the $250 price point I doubt you'll find something that remotely compares to nice monitor speakers. Spend $100 on something decent like the HD280s and you should be happy.
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