I've talked a lot about how I present myself to the world. I grew up getting dressed up to travel. And while it is sometimes tempting when I have a 5 a.m. flight to take it down a notch, I still don't allow myself to look like a ragamuffin while I'm traveling. And every time I run into an exec from work at the airport or a good looking guy at the gate, I thank myself for not putting on my onesie and saying "Whatever!"
I'm also not insane. No way I'm going to sit in a pair of jeans that have no give because I want to look good on an airplane. There are plenty of ways to look put together and still be comfortable. When in doubt, a leather jacket is a good place to start. I was also only gone for 48 hours so I wanted to bring a jacket I knew I could wear with everything in my suitcase.
I opted for a pair of black Athleta pants, a crisp white tee and a black leather jacket. I tied one of my favorite Madewell sweatshirts around my waist and threw on my tennis shoes that have a pop of cobalt blue. And of course I had my go to Chanel Supermodel Tote - my throw everything that I could possibly need when I travel bag.
PS: my sweatshirt reads, "So Far, So Good."