Popular culture represents the clothing choices of teenage boys in the 1950's with surprising accuracy. From sweater vests to leather jackets, stereotypes like the "greasers" and "socs" from S.E. Hinton's "The Outsiders," for example, ring true when compared to photos from that period. In the first two lines of the novel lead character Ponyboy wishes he looked like Paul Newman, demonstrating the strong influence of entertainment on the style choices of that era.
Classic Preppy Casual
The first thing you notice viewing pictures of teens in the 1950's is the neatness of their dress. Whether wearing their long-sleeved button-up shirts with or without sweater vests, teenage boys knew that pressed and tucked were the order of the day. In "The 1950s and 1960s," author Anne Rooney presents the Nelson brothers from the popular TV series "Ozzie and Harriett" as examples of 1950's style for teen boys. Jeans had a place beside slacks, and T-shirts even made the occasional appearance, but the clothing was always fitted and neat in appearance.
Greasers and Rebels
The young man in a black leather jacket with a pack of cigarettes rolled in his sleeve is a 1950s stereotype that rings true when observing photos from the decade. According to Rooney, these jackets and T-shirts appeared next to jeans or twill "work pants." The standard ensemble of the rebel or greaser also included heavy boots, or occasionally Converse All-Star sneakers. As with other casual clothes of the era, those white T-shirts with the rolled-up sleeves were always neatly tucked into belted pants.
Formal Wear
Although modern formal wear allows some latitude regarding ties and collars, dressing up for teenage boys in the 1950's included the full business suit. Neck ties, starched collars and pressed, pleated slacks made up the formal ensemble, while shiny leather loafers completed the look. Self-expression still found its place in pastel-colored suits or brightly toned dress shirts.