Ah, flying! Such a necessary evil. I hate flying even though I do it ALL THE TIME as all my family is still in Puerto Rico. I do think that I've got travel-wear down to a science.
These are my recommendations:
1. Pants are your friend.
I always wear my dark-wash jeans when I fly, they can get dirty, they are comfortable and they will not wrinkle or look weird once I land. If you are one of those strange creatures who doesn't wear jeans–I really can't wrap my mind about this concept, but that's another story–then any other pants will work, like these pants from JCrew.
Camp Pant, J. Crew, $69.50
Hell, even leggings are totally flying-appropriate; just don't wear them as pants, please! My rule of thumb is that the top must cover your butt with like maybe 2 inches to spare and the thicker the fabric the better. These cotton-modal blend pants by T Alexander Wang would be a good option.
Cotton-modal blend pants, T Alexander Wang, $150
2. Layering is key.
As it is so often when we are navigating a variety of temperatures in a small timeframe, layering is key. I usually wear a my favorite light button-down shirt, a cool plaid "Perfect Shirt" from JCrew.
Perfect shirt, J. Crew, $88
I think button-downs automatically make you look put-together and let's face it, I wear them all the time anyways. The shirt's breezy enough to withstand the balmy tropical temperatures of Puerto Rico and with the addition of a light cardigan during the flight I'm as warm as can be. I like to carry an oversized cardigan in my bag because I can also throw it on me blanket-style. This knitted deep-v number from–gasp!–Jessica Simpson is actually perfect.
Neck Long Sleeve Oversized Ribbed Knit Cardigan, Jessica Simpson, $17.99
3. Don't forget your socks.
SOCKS ARE SO IMPORTANT! Nothing grosses me out more than when I see people barefoot while waiting to go through security, it's almost a step above being barefoot in a New York City sidewalk because it's all INTERNATIONAL GERMS! I don't think I can stress this enough, don't fly in flip-flops either. I mean I'm kinda against flip-flops in general (unless you're at your house or at the beach) but if you have to run to catch a gate or something being in flip flops will be dangerous. Or what if a suitcase falls on your toe? There goes your nail! I generally fly with my brogues (they're stretched out enough that I don't have to tie and untie them, easy shoes to put on are also key!) so wearing socks isn't a problem, but if you want to wear a ballet flat or other shoes that don't look good with socks then just keep a pair of socks in your bag and put them on once you get to security (and later on, the plane).
Flying is about being comfortable. The airport is not the place to dress up like you're going for a fancy party or just got out of bed. I mean it's cool if you can swing being fancy, mobile AND practical, but I feel like most of us aren't, so what's the use of complicating an already stressful experience with delicate clothes?