Boxy and relaxed rather than tailored, this brown leather jacket is made for daily wear. Easy to throw on, and it only softens with use.

Dramatic volume defines these wide-leg black jeans from Willy Chavarria's Bad Boy line. The exaggerated proportions are the whole statement.

A woven-leather upper gives this dark-brown Timberland 6-inch added texture over the standard model. The icon, dressed up a notch.