I am tempted to try some earbud style
  headsets - over-the-head models puts such a crimp in my follicly challenged
  hairstyle!

Matt,

 

I have a pair of model one Bose Headsets, purchased in the very early 1990's.  They still work even though I had to replace an end connector on one (Bose used an off the shelf plug), but Bose no longer supports repair of these ancient headsets although they are willing to accept them as a $300 trade in for newer ones.  The problem is that the model one hard wired interfaces are not compatible with the new Bose deVICES.  The Bose model one is my backup headset or available for use by a passenger, if any.  The noise canceling was mostly worth the discomfort.

 

I finally installed a second path to the audio panel - standard aviation sockets, usable by any headset.

 

I currently use the Aloft Technologies' Clarity ear bud style "headset" (http://www.clarityaloft.com/) because of the following benefits:

 

1. They are extremely comfortable during long flights.  Hmmmmm, that's true for short ones, too. 

 

2. The wire microphone support allows me to start the engine without the bud(s) inserted, listen to ATIS and ground thru my 2" console speaker and still talk to ground.  The microphone is excellent.  One must remember to insert the buds before flight.

 

3. There is an 1/8" stereo socket in the volume control that allows for cell phone plugs, MP3 players or, in my case, audio from my portable XM radio.  My installed audio panel and system are mono and the Clarity bypasses that restriction.

 

4. No clamping pressure and no discomfort from perspiration generated during hot weather or by some silly pilot error.  It does not compress the hair atop the head or around the ears, if any.

 

5. The small microphone can be placed at the corner of the mouth so that in-flight eating does not soil the foam cover or require that it be moved aside.

 

6. It is easier to scratch the inside of one ear tickled by ear hairs and still hear ATC thru the other rather than removing the twisting interlocking Bose.

 

There are some drawbacks:

 

1. Clarity does not cancel the noise so that low frequency noise is slightly higher and different than that heard with the Bose.  It did require getting used to after years of ears betwixt the Bose, but it is not loud.

 

2. I have placed a rubber band abutted to the volume control because it is too easy to move since the module lays alongside my leg.  The 1812 Overture could sound like the final act of a horde of suicide bombers just because I moved my knee.

 

3..................Uh......................... can't think of any more.