For winter/fall (there is really no difference once you go north of DC anyway) travel, I like to wear as many layers as I can and absolutely avoid sweatpants/sweatshirts at all costs. There is no reason to look like a slob when travelling! This way I didn't have to change once I got to my grandparents' house either.
I love love LOVE these boots, by the way, and highly recommend them to anyone looking for the perfect fall bootie! Not only are they cute and on trend, what with the goth look coming back in style this year, but they are also lined on the inside and they slip on, so they are hassle-free and warm, both of which are perfect for airports. Find them here for only $20 if you sign up.
Jacket- Banana Republic
White shirt- Forever 21
Skinny jeans- American Eagle
Booties- "Micah" ones from JustFab
Earrings- Library of Congress (!!)