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Start with your favorite white t-shirt. You'll be wearing it for a while, so make sure it's so fresh and so clean.
Taking into account that you'll be sitting for a while, opt for your most worn in and comfortable jeans. You know exactly which ones we mean.
With TSA security checks, you'll need a pair of shoes that can slip on and off easily. Go with a really comfortable pair—you may be standing on line for a long time.
Okay, now it's time to add another layer. Find your favorite button-up and put it over your t-shirt.
The layering continues. If it's cold where you are, protect yourself from the temperature by adding a cardigan over the button-up. It can be chunky or simple, doesn't matter.
Now start building up your outerwear. Find a light vest that you'll be able to store in a carry-on if necessary. The Uniqlo down vests fold down to be almost paper-thin. Alternatively, if you already have a quilted vest, that's an equally solid option.
Add a jacket for your final layer of outerwear. If you're heading from the Northeast, you'll be toasty warm when you leave and can easily get back down to t-shirt and jeans when in no-time upon landing. Just throw the extra layers in your carry-on.
Sitting in a confined space for several hours isn't fun. One trick I've learned over the years is to pack a pair of clean socks in your carry-on. After the security check-in, the waiting and the boarding, your feet have been through a lot. Changing your socks mid-flight gives you and your feet a new lease on life—a happy lease on life.