WHY YOU'LL LOVE THEM: The Bobby chukka Boot is a great all-rounder perfect for early morning commutes and dinners out with the family. With a tumbled leather upper and sturdy rubber sole, these ankle boots will be a timeless staple in any man's wardrobe. WEAR THEM TO: A classic chukka boot like the Bobby lends itself to any smart casual occasion on your calendar. Work? Drinks after work? Weekend errands? Tick. Tick. Tick. These boots add a level of polish to make anything you wear feel purposeful and put together. WEAR THEM WITH:A classic chukka boot is as easy to wear as any Chelsea boot or military boot in your wardrobe.