You guys, I just scored this (hilarious) one piece that covers eeeeerything on clearance at Lord & Taylor ($39). It is not the sexiest suit by any stretch, but that's pretty much the point. This is for those days when I'm bloated and can NOT be bothered to try to be cute.
Whether or not I actually wear this in public, we shall see, but the idea that I even own this option is comforting!
After strategically putting everything for our wedding on our Southwest credit card (and then immediately running home and paying it off!), the hubs earned enough points for a Companion Pass. This means that, for all of 2014, anytime he buys a flight he gets an extra seat for me for free! Between flying to the East Coast to see my niece/nephews, weddings, and our jaunt to Puerto Rico, I have become quite the expert in in-flight comfort and style.
I always like to layer because you never know if your flight will be freezing or not. Thin cotton layers are great because they fold up into nothing. Cardigans are easy to take on/off, and a hood always makes a nap feel cozier. I always bring a scarf to use as another layer, a blanket, or even as something to sit on if the seat skeeves me out!
Black "Magic Pants" (aka 5-pocket ponte skinnies) are as comfortable as leggings, but still give you pockets to stick stuff in. Please do not wear pajamas in public: I promise Magic Pants and a drapey cardigan are equally as comfortable and infinitely more attractive.
I like to wear shoes I can wear with socks, so I don't have to do the gross (and ineffective) tip-toe through security. Slip on sneakers are easy to take off/on, and if they have decent arch support, they are also useful for the rest of the trip.
A good tote makes for an efficient flight experience. I like outside pockets to put my ticket, ID, and phone in a convenient place. Inside pockets and/or small zipper bags help separate my everyday things from the stuff I'll need in-flight. I have a large zippered clutch that I put my tablet, headphones, and charger in (which also doubles as a purse once we get somewhere). I also have a smaller pouch for things like medicine, lip balm, etc.
One last item which is clearly over $25 is the carry-on. I highly recommend a DVF piece. I've had mine for almost 10 years and it's still in beautiful shape. You can usually find them at stores like TJ Maxx for about $70.
I love the idea of the Boyfriend Jean, but every time I try one on I feel they look ridiculous on me! My top secret solution is to simply buy regular skinny jeans (like these Lauren Conrad's) two sizes too big. (P.S. how adorable are these special edition Marimekko Jack Purcell's I scored at Nordstrom Rack!?)