The Shoe: UGG® Classic II Genuine Shearling Lined Tall Boot ($200) Why it's great: "These classic UGGs are perfect for the winter. They are nice and warm but I can still go outside in these boots compared to my slippers. And I can wear them with leggings, jeans, and even a dress if I am feeling a little fancy." — Lauren Hendrickson, Head of Shop and Affiliate Growth