64. Wingtips

With the emergence of hard-bottom shoes, the classic patterned W-shape cap toe reappeared in many collections in the latter Aughts. The traditional country-club shoe has a wing-tip pattern that always lends an air of sophistication. No white socks with these, people.

LEADERS OF THE PACK:
Lanvin, Brooks Brothers Black Fleece, Florsheim by Duckie Brown, Barker Black