My rules when traveling are pretty simple: be comfortable, but not so comfortable that you make other people uncomfortable. I'm talking to you, airport pajama wearers. Step away from the sweat pants.
There's something about flying that I still find chic, if you can get past all of the ugg boots and flip flops of your fellow travelers. It's an opportunity to take a long layover, sit at a table alone and sip coffee while you type on your laptop and re-invent yourself. I often pretend I'm a ridiculously successful fashionista who is very busy and important (and cannot possibly find a direct flight? Whatever). Whatever fantasy you make up for your airport adventures, dress the part. I found these wedge boots to be ridiculously comfortable without being embarrassing, and the leather-look leggings were so comfy, I hardly noticed I was even wearing pants.
I'm actually planning a really fun little post for you right now on my travel outfits! While I'm still going to show you what I wore every day, I'm also going to show you how I could remix everything in my suitcase to suit any outing or situation. I think it's important to look for pieces that are really re-mixable when you're packing light, so keep an eye out for that in a few days.
Boots, JustFab (thanks to autopay!).