This feature originally appears in Complex's August/September issue.

This is the year of the Chelsea boot, and if you haven’t quite hopped on the trend yet, consider this your signal to officially get on board. You still get a late pass, though. Whether you opt for the classic elastic upper of a Chelsea boot or the strapped-up look of a Jodhpur, the upscale appeal is the same across the board—it’s a grown-up shoe that looks as good with a pair of ripped, washed denim and a white T-shirt as it does with a crisp pair of slim-fitting trousers and a suit jacket. When it comes to materials, suede is the classier option, though it requires more upkeep than smooth leather. Either way, the added ankle height won’t just help your vertical; it’ll take your style way, way, way up, too.

Above (left to right):
Saint Laurent by Hedi Slimane, $895, available at ysl.com
Christian Louboutin, $1,195, available at us.christianlouboutin.com
Aquatalia, $450, available at aquatalia.com
Bally, $995, available at bally.com
Tommy Hilfiger, $279, available at tommy.com
Common Projects, $530, available at commonprojects.com


 

Tommy Hilfiger, $279, available at tommy.com
Common Projects, $530, available at commonprojects.com