Often it's the simple travel gear tweaks that make a difference. Here's a dead simple one with huge results: a hat with a folding brim.
Packing a baseball cap or something similar is a pain. In your checked luggage it gets crushed and bent. In your day pack it gets in the way. On your head you have to take it off at every security check. But what if you could just fold it and stick it in your pocket or stuff it between a book and a magazine in your day pack or laptop bag? Enter the Radar Pocket Cap from Outdoor Research.
I just used one of these for two weeks on the road and it delivered as promised. I folded and unfolded it about 20 times and it kept its shape. I carried it on the plane going and stuffed it into my checked bag coming back. It still looked good, stylish even in a Fidel kind of way. (But Fidel would never wear it in "burnt orange"--one of the choices.) It lists for $24 and I'm confident it's going to last. If it doesn't, well the tag says, "Outdoor Research products are guaranteed forever."
The only drawback is there's no give anywhere so you have to know your head size to order it. Get out that measuring tape, then go pick your color at the OR Radar folding cap page.