Keeping it simple is almost a requirement for traveling - but knowing how to do it without always feeling underdressed is a whole other situation. My little trick is to find pieces that stand out on their own, but that I can wear more than one way, and more than once in a week without looking like I just forgot to bring enough clothes.
Everlane makes this easier than ever - during the trip, I wore these culottes with a crop top and also a cami, the sandals with basically everything ever, and this top with shorts, as well as tied up the way I'm wearing it here. And while I'm often sick of things I packed for a trip for a week or two after I get home, these are pieces that I'll immediately look forward to wearing.
Photos by Nikko DeTranquilli