That being said, I've now pared down flying to a science. Patience isn't my best virtue, and for that I've got the outfit down to a science to get through the airport security lines as swiftly as possible.
Here's my "Dress for Success: Flying Edition"
Usually I include a thin cotton J.Crew wrap sweater in my bag, but I never wear it until I'm through security due to the fact that I'll only have to take it off anyways. Since there's nothing I love more than leggings--and because I don't like sitting for a long period of time in jeans-- these Hue equestrian leggings are perfect, and simply the most comfortable leggings ever. My go-to outfit always includes leggings or jeans and a J.Crew t (since they're simply the best). I pair almost all leggings or jeans with my Frye boots that I received for Christmas seven years ago. I couldn't find a picture of the boots (obviously) now for sale, but the ones above are fairly close. I barely wear jewelry when I'm flying, but the one thing I always keep on is my Saint Christopher's necklace that my parents gave me for "safe travel" (st. chris is the patron saint of that) and it's in an aqua-blue enamel. Aside from an obligatory watch and suitcase, my favorite accessory is my blue pashmina. I can roll it up and wear it as a scarf, or completely unfold it and use it as a blanket on the plane.