Usually TSA makes me take off my scarf, jacket, and shoes at the checkpoint. In an effort to not feel like I'm undressing in public, I go ahead and store those first two items in my tote ahead of time. Ballet flats make for easy last minute shucking.
My faithful travelling companion will always be one of those "everything's $10" faux pashminas that are found in airports everywhere. It's large enough to double as both an accessory, as well as a blanket or pillow, which is great since most airlines have gotten rid of those items onboard.
I can't get enough of leggings this fall, though I've never really cared much for them before. I found this tunic at Old Navy over the weekend and loved how comfy it looked. I think it would equally perfect in a cabin at cruising altitude and a cabin in the woods. Really, this outfit is like travel-appropriate pajamas. That's a win.