Comfort is key for me. I’m usually hot/stressed until I’m through security, and then I’m freezing once I’m on the plane. For winter, I prefer stretchy jeggings, a comfy sweater, and shoes that slip on and off easily – whether they’re riding boots, ankle boots, or flats (though I HATE walking through security without socks).
J Brand Jeggings
Rag & Bone Motorcycle Boots
J. Crew wide cashmere scarf doubles as a wrap/blanket