Every time I put on an outfit I think, “I got a fever! And the only prescription is more boot heels!” Crazy stuff is going on in my head, which means I have officially crossed over into obsession. Even though my mind is clouded with my love for these boots, they actually fill a very practical void for winter: Something dressier than winter boots. The low thick heel is perfect for icy sidewalks. And I can’t help but love the odd pairing of sporty and dressy. They are kind of like a hooded dress, which I still can’t find any justification for wearing.

1. Jeffrey Campbell ‘Loggins’ Oxford, $169.95
2. J.Crew Eliza lace-up boots, $350
3. Forever 21 Combat Ankle Boots, $35.80
4. Steven by Steve Madden ‘Isolate’ Ankle Boot, $159.95
5. Workman Lace-Up Bootie, $27.80