The purpose of this study was to explore the classic American style labeled ‘Preppy’ to evaluate and interpret its static and dynamic elements. The heritage and foundational garments that encompass the style can be traced as far back as 1852 in the Cambridge University General Almanack and Register, yet this research begins in 1962 when Esquire magazine presented an editorial, The Basic College Wardrobe. This editorial depicts dressing in a formulaic manner, so men of all backgrounds could achieve the ‘Preppy’ look. Through a content analysis of Esquire’s September issues from 1962 to the present, I began to look for today’s quintessential ‘Preppy’ uniform in advertisements and editorials to see how it evolved and came together to be the timeless look it is today. Examination of the content revealed that ‘preppy’ proves to be a very complex fashion tribe with roots tracing back to Britain, but there appears to be a specific uniform that’s prevailed throughout the lifespan of this particular style. Preppy style stemmed from Ivy Style and was merged with several other fashion tribes: WASPs, Dandies, Athletes, Military, Go-to-Hell Look, and Japanese Ivy Style. Through the convergence of these styles, an established look prevailed: oxford button down shirt, khaki pants (also known as chinos), navy blazer with gold buttons, repp tie, and penny loafers. Understanding the origins of these individual pieces will inform our understanding of the significance of why ‘Preppy’ has remained a relatively static uniform over the years.