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It depends on what kind of headset you like, really, which is a personal decision. I'm comfortable with single-ear headsets like the Plantronics Audio 920 bluetooth headset; but other people might prefer dual-ear headsets like the Sennheiser PC 151 or perhaps one that fits better on your left ear. Personally, I find the dual-ear headsets too sweat-inducing.
I haven't used Skype more than a few times, but it's important to understand that Skype and other VoIP can offer better sound quality than POTS (and possibly cellular), since they can (although may not be) using more bandwidth and therefore better frequency range...so POTS-class headsets may not be what you want.
I doubt there's any headphones "optimized for use with Skype."
Depending on how/where they'll be used, a boom mike is likely to give better sound. Do you want one earpiece or two? Will it be indoors or outside? Will sound-suppression (wind, lawnmowers, etc) be needed? Are you planning to do more talking or listening? Do you also want to use it for music-listening? Gaming? Dictation for voice-recognition?
My opinion: Answer these questions, and then go to NewEgg.com, and also to
HelloDirect.com, and stick to your budget.