The North Face Shellista III Tall Waterproof Winter Boots (thenorthface.com, $120)
Not only are these boots trendy, they’re also lined with super-warm fur that makes them snug, fancy, and incredibly cumbersome to put on. After struggling with them for a couple minutes, you’re just going to kick these aside and put on an old pair of gym sneakers. They’re already tied so just shove your feet in there until they don’t slip off and head out. Sure they’ll get super damp, but at least you didn’t have to sit down to put them on!