I bought these boots years ago, and just thought they were so cool. I’m not going to lie though, they’re difficult to wear. It took me a while to figure out how to style them without looking like “Pretty Woman.” Now that OTK boots are a little less new and a little more trendy, its definitely easier to pull them off. I’ve come to the conclusion they look best with skinny jeans or a dress that is completely covered on top, read: high neckline, long-sleeves. You can’t have your boots go up to there and flaunt skin up top as well or grams will have a heart-attack. Even with a skirt, I always pair with tights just to add an extra layer of “fashion.”

Dress: Torn by Ronny Kobo (emeral green version on sale here and also here!). Vest: Intermix (similar here and here, faux version here). Boots: Fendi (similar here, steal here!). Jewelry: David Yurman, Cartier.

Photos by Felicia Lasala.