India, March 18 -- After years of traveling, I've learned that the best travel outfits are the ones you're just as happy wearing at your destination as you were on the plane. Sometimes your hotel room isn't ready yet, or you've had a long travel day and don't want to waste time changing-you just want to drop your bags and start exploring. Whether that means wandering cobblestone streets in search of lunch or heading straight to dinner, it's always a relief wearing something you feel confident in (and wouldn't mind being photographed in).

Lately, I've been building outfits around versatile staples that work for the entire day ahead and throughout the trip-pieces like a cozy two-piece set, an oversized blazer, and classic loafers. I also l...