Not quite shoe, not quite sneaker, and not quite boot– don’t let the “bootie” thing scare you. These 3:33 shoes are a slick boot version with a back ankle snap, tab, and an interior side zip. Dark grey leather makes for an interesting look in comparison to all those jet-black pairs, and is lined completely in leather. Sneaker-style sole keeps you stuck on the pavement and not slipping about in stormy weather. Fold ‘em down for the full effect! Available in sizes 8 and 9 at Oak NYC.

Buy: $220