Khaki warms up the stripe's cool blue-and-white without erasing it, landing somewhere between prep school and actual comfort. The straight fit pant has a real gusset built in, which you will only ever notice by not noticing your legs during a long car ride or a red-eye. This is the outfit for the trip that starts with a rental car and ends with a hotel you found at 11pm the night before. It's a comfortable men's travel outfit that still looks like you packed on purpose.

Finish with tan suede sneakers and a canvas duffel with a strap you actually trust.