75. Going Sockless

When it became fashionable to cuff your pants, or get your trousers hemmed without a break — so ankles were clearly visible, socks started disappearing from the tops of shoes everywhere. Ushered in by designer Thom Browne, whose slim, cropped silhouettes favored sockless looks, it became quite popular in the world of menswear, and you would spot many guys wearing really nice loafers, wingtips, and oxfords barefoot. Of course, some only committed halfway, and opted for no-show socks.