• Flannel has been made since the 17th century.

Vans Era 59, $65

The Sneaker

Nothing says "smart, but not too smart" quite like a pair of low-profile sneakers in an unusual material. After all, a man can't live on lace-ups, loafers or desert boots alone. And these three here—all seasonal takes on age-old styles from such go-to brands as Vans and SeaVees—have one foot in the suit department while the other is firmly planted in the street. The sharp flannel styling makes them look a whole lot more expensive than they really are. With their streamlined, subtle profiles and steely wool material, these are more than simply off-duty kicks. They'll work with everything from your favorite dark jeans to a slew of office-appropriate trousers. The fact that they keep your feet warm as temperatures dip is merely a bonus.