The preppy style is timeless. Cardigans, polo shirts, and Mary Jane shoes — all staples of the fashion — will never truly go out of style. American prep style has survived brand bankruptcies (J. Crew emerged from bankruptcy in 2020, per a press release from the retailer), store closures, the rise of athleisure, and hype beast trends. It has never really gone anywhere. Rather, it’s simply evolved.

From its not-so-humble beginnings in the 1890s and early 1900s to a revival in the 1980s and 1990s, it’s evident that the preppy lifestyle isn’t going anywhere. Even today, we still love preppy style — as evidenced by celebrities such as Victoria Beckham and Yara Shahidi, as well as designers like Chanel and Ralph Lauren.

Ready to take a deep dive into the preppy aesthetic? Let’s take a look at its evolution before we give you tips on how to wear the trend.

The Origins of Preppy Style

Back in the late 1890s and early 1900s, the “preppy” style was a sort of status symbol worn by wealthy guys who went to preparatory and Ivy League schools — hence the name. Brooks Brothers button-downs, knit sweaters, and loafers were all part