I wear a cap when I fly but it's only to keep the sweat off my face. Those classics are smokin' hot in the summer. I think it's more old school than new school. Have you seen the white gloves yet?
I've seen guys occasionally wear a cap while flying for years. I don't, but it's probably a healthy habit for avoiding uv rays.
If anyone is bothered by it, they should consider the possibility that they have issues and should seek help to perhaps not be so anal.
It makes sense when you're flying an airplane with eyebrow windows. When you're not you look like a guy who wishes he was flying an airplane with eyebrow windows (or one that's begging deep down that you'll ask him what the F-15 was like to fly).
It doesn't meet the FAA requirements of donning a sweep-on or quick-don oxygen mask. The test for putting on the mask doesn't include the time it takes to take off the headset, takeoff the hat, put the headset back on, then put the mask on. Most airlines don't know or don't care, but if there is a Fed in the jumpseat, I wouldn't wear one. O2 masks have become a big emphasis item recently. Sooner or later, they're going to decide to make a point of this.
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