Clogs are my secret hack when it comes to comfortable travel shoes. They're versatile enough that I can easily pair them with my casual running errands outfits or dress them up to get drinks with friends. They're also a dream to fly in, because they're easy to slip on and off, making airport security a breeze. You'll even be able to treat them like slippers on long flights when you want to slip off your shoes (with your socks still on, of course!)
Jackets should be lifetime investment pieces; don't fall for trends here. Get something stylish, get it on sale, but make sure it'll provide you with an easy way to level up an outfit for at least a decade. Throw the lightweight layer on over a plain T-shirt and jeans and suddenly you're the coolest guy in the room. Pair a chore coat with your favorite pair of chinos for the easiest way to achieve a laidback, Parisian-esque everyday look.