Our Legacy 3-Roll 2 Grey Tweed Sportcoat, $550
Ralph Lauren Custom-Fit Brushed Blue Plaid Shirt, $55
Burton Premium Full-Zip Sleeper Hoodie, $99 

Let's face it: you get more respect looking presentable at an airport. Combine comfort and style with an unstructured blazer in a heavier tweed fabric, perfect for brisk weather. A brushed twill shirt like this blue plaid from Ralph Lauren feels awesome without being itchy like wool flannel. You'll want to live in it. Plus, you can even wear it under a hoodie, like this Sleeper Hoodie from Burton that offers a lot for weary travelers. We're talking an inflatable neck pillow and an eye mask that folds down from the hood, hidden pockets for tickets and passports, and a place to slip your headphones through.