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!?)
Speaking of vacation/summer uniform, shorts can be a terrifying affair. There was a loooong period in my teens and 20s when I refused to even wear shorts: I felt they were cheesy and definitely not elegant. But eventually, I learned to embrace the short by taking an ironic approach to them. I started by wearing destroyed, self-made cutoffs with heels and sparkling jewelry. Now I keep it a little less extreme, and have found that American Eagle Midi Shorts are the perfect amount of "oh these old things?" worn-in and have a modest length (aka no butt cheeks hanging out).
I had planned on taking a ton of outfit pics during my trip to San Juan, but this was pretty much my uniform the entire trip: tattered denim shorts, plain tank top, comfy sandals, and a bunch of bright accessories. A square scarf is the ultimate travel accessory because it folds up tiny in your bag, but can be used for warmth, protection against the sun, emergency hair help, something to sit on, and even as a pool cover up.
earrings and scarf: Forever 21 // tank: Mossimo // shorts: American Eagle //
shoes: FitFlop // sunglasses: LOFT // purse: Rachel Roy //