I always steer towards wrinkle-free fabrics like microfibers, Lycra®, wool, and polyester that double duty day or night. For example, black yoga pants balance perfectly between working out and going out.
Shoes can be heavy and bulky, so be extra critical here. No matter the destination, three pairs is my limit. On surf safari I could get away with just flip-flops for a whole week. They may be a little exposed at SFO in February, but in Puerto Vallarta they fit right in.
TIP: I wear my heaviest shoes on the plane. I stuff the others with socks and underwear to keep their shape and pack them in freezer bags so they don’t share odors.
When city-bound, I take shoes I can wear all day. If staying in a hotel with a gym or near a park, I pack lightweight cross-trainers. For a night out, black ballet flats can get a table by the window or make a mad dash for the subway. And don’t forget to test your shoe choices against your travel wardrobe. You might not need those candy red pumps.
TIP: Never test new shoes on your trip or you could end up carrying a pair of unbearable wedges all through Europe.
Put your chargers and adapters in a clear freezer bag for easy retrieval. I don’t pack little speakers if my iPhone plugs into the hotel clock radio, so I bring a short audio cable to plug in my phone for music. I used to bring network cables, but not anymore because wi-fi is everywhere.
TIP: Back up your data before you leave!
TIP: Put a sticker with your contact info on your tech in the event it gets left behind at the cafe.