The Boot: The Dicker by Isabel Marant
Price: $630
Material: Suede
Pros/Cons: They’re a cult classic, beloved by style icon Kate Bosworth, and we’ve never seen someone not look super chic while wearing them. They’re also only 2.5″ high, so, comfort.
Cons: They’re pretty ubiquitous, a little trendy and there are a ton of knock-offs, some of which are pretty convincing and a whole lot cheaper. Still, none of them quite match up to the original. They just have that je ne sais quoi. Also, though, suede is a little tricky to pull off if you live somewhere that has seasons.

Buy them here.