India, May 9 -- Don't judge, but I've been traveling for 30-plus years and have checked a bag on nearly every trip. (Surprisingly, my luggage has only gone missing once.) I didn't want to lug my suitcase through a busy airport or wedge it into a cramped bathroom stall. At 5-foot-1, the idea of hoisting a heavy bag into the overhead bin made me sweat. Mostly, I packed for every possible "what if" scenario that could crop up on my trip.

It wasn't until I started flying more regularly that I realized I needed to rethink my packing habits. Waiting at baggage claim felt like wasted time, and I couldn't ignore the fact that I was wearing only half of what I packed. That's when I decided it was time to become a carry-on-only traveler. Since the...