After my last trip, I started my own "Trip Packing Hall of Fame." Yeah, I'm a little weird..... probably just like you :) Here's the inaugural class of the half of fame:

1. "Performance" Untuckit shirt Long sleeve, light weight, & easier to adjust to changing temps on planes/trains/etc. than taking on/off a sweatshirt. Just roll up/down sleeves or button/unbutton the front. "Performance" means synthetic materials so wrinkles fall right out. Nice enough for a dress up meal too. Feel fine sticking it in a backpack since the wrinkles fall out.
2. Portable sleep machine that's very compact, feature rich, & USB-charged (so you don't have to use an outlet near your bed). Been sleeping with a much larger one for 40 years. A great night's sleep when traveling is worth a lot to me, but this machine is only $33 and very small.
3. Roll-up backgammon set is always with us. Nothing better than walking through a cool town/city, then sitting at a cafe/bar for drinks and some backgammon. This one is pricey, but VERY well made and much more compact than a folding board. Warning: TSA always flags it on carryon (b/c of magnets, I guess), so my wife keeps it on top of bag.

I invite each of you to start your own Hall of Fame...... Have fun!