It sounds silly but having decent luggage can make a disproportionate difference when it comes to how much you enjoy your traveling experience.
Act like you’re going on a terrific trip right from the start. Don’t get on the plane (or in the car) in your sweats hauling your old gym bag. Put on a nice pair of jeans, comfortable shoes, and a casual blazer, and you’ll instantly feel better about the entire thing. Get a great looking weekender bag like this plaid wool-sided small duffle from Fossil, and it’ll only ratchet up the experience.
That and the cute girl in your row, or if you’re really lucky the passenger seat, will take notice of the one well dressed guy in her vicinity.