1. Faherty Shirt Jacket, from $74: For a top layer, I’ll choose either a soft hoodie like Buck Mason’s Brushed Loopback hoodie or a brushed cotton shirt jacket (“shirt jack” or “shacket” if you like), like this one from Faherty, or a Transitional Flannel from Outerknown (if anyone knows how to travel, it’s Outerknown founder Kelly Slater). Essentially, anything that’s soft and comfortable enough to double as a makeshift blanket or pillow will do for me.
Buy it here: Faherty
2. DSTLD Skinny Slim Jeans, $75: I’ll almost always wear jeans on the plane, but I’ll veer away from donning my tightest or most rigged raw denim and choose a pair from DSTLD, which are made with just enough elastane so I don’t feel too constricted. I live in jeans, even in the doldrums of summer (unless I’m swimming), and apart from the few times I’ve seen the inside of a gym, I won’t wear sweatpants out of the house.
Buy it here: DSTLD
3. J.Crew Tee, from $19.50: For casual travel, I tend to grab a soft cotton T-shirt from J. Crew. They’re comfortable, lightweight, and make a good base layer.
Buy it here: J.Crew
4. Onia Abe Shirt, $135: If I’m traveling under more formal circumstances, a linen Oxford from Onia is a favorite, which I’ll wear underneath a blazer (I go for a plain one from J. Crew when they’re on sale).
Buy it here: Onia
5. Sperry Original Leather Boat Shoe, $94.95: My travel shoes are about the only shoes I’m willing to wear anywhere, if and when I must wear shoes. Sperry Topsiders are unbearably cliched for some, and I understand, but they’re still the simplest and most comfortable widely available piece of footwear I’ve encountered. They’re easy to slip on and off and get through security, even when your feet are swollen from flying.
Buy it here: Nordstrom | Sperry | Amazon