If you're looking for printed leggings, ironic t-shirts, and all things fast fashion, you head over to State Street. But if you're looking for shoes that will make your rent look cheap in comparison, you head over to North Michigan Avenue. The Magnificent Mile—that glittering stretch of Michigan from the Chicago river to the Drake Hotel—has been a high-end shopping destination for decades, and a new exhibition at the Chicago History Museum explores the way in which North Michigan Avenue developed into one of the greatest upscale shopping destinations in the country.

The exhibit, titled Chicago Styled: Fashioning the Magnificent Mile, features 26 outfits, chosen by curator Petra Slinkard, that range from the late 1950s to the mid 1990s. “All the pieces in the show were selected as a means to represent one aspect of the development on Michigan Avenue,” says Slinkard. That means you'll see everything from a '58 jumpsuit to early '90s pieces that are just starting to conjure up the grunge era—and it's all deeply rooted in Chicago history.

If you think the Magnificent Mile is fancy now, you should have been there during Prohibition. “In the mid 1920s through about the mid-20th century, we saw a lot of independent Chicago high-end specialty boutiques open [on North Michigan Avenue], such as Blum’s Vogue and Stanley Korshak,” says Slinkard. “Then Saks Fifth Avenue decided to expand within the States and chose the Magnificent Mile as their second US location in 1929.” Back then, the environment was more purely high-end than it is today. (There was also a shocking lack of today's vertical malls. Ah, simpler times.)

It was after WWII that the street's retail scene really began to boom. “The '50s and '60s were an era of development and planning,” says Slinkard, “and then by the mid-'70s we saw the construction and completion of the John Hancock Center and Water Tower Place. The two anchors of Water Tower, when it opened, were Marshall Field and Lord & Taylor. Within Water Tower you start to see the range: Halston, André Courrèges, and other high-end boutiques, but then you also see one of the first Gap stores opening. There's more of a democratization—a nice turning point, where we start to see a hint of the Magnificent Mile that we known today.”

One of Slinkard's favorite pieces in the exhibit embodies both fashion and narrative: It's a custom ensemble donated to the museum by a Chicago cosmetics company called Jovan. “To market their first perfume, [the company] found a well-known 1970s designer named Malcolm Starr, who created this ensemble, the pants of which are completely encrusted in pearls, rhinestones, and Swarovski crystals,” says Slinkard. “Not only is it a beautifully striking piece, it's one-of-a-kind and absolutely tied to Chicago. It's a perfect mix of all of the best elements of a story like this—the entrepreneurial spirit, the idea of cosmetics and fashion coming together, the idea of going out on a limb and approaching a designer personally—and to add to the story, Jovan contacted [the Chicago History Museum] directly in order to donate the piece. It's a wonderful Chicago story: this Chicago company was interested in supporting their city's museum and wanted to preserve their legacy.”

See all the jumpsuits, crystals, and early grunge ensembles yourself. Chicago Styled runs through August 16, 2015 at the Chicago History Museum, 1601 N. Clark. More info at chicagostyledfashion.com.