In the 1960s, Yorkville flourished as Toronto's bohemian cultural centre. It was the breeding ground for some of Canada's most noted musical talents, including Joni Mitchell, Neil Young and Gordon Lightfoot, as well as then-underground literary figures such as Margaret Atwood, Gwendolyn MacEwen and Dennis Lee. Yorkville was also known as the Canadian capital of the hippie movement. In 1968, nearby Rochdale College at the University of Toronto was opened on Bloor Street as an experiment in counterculture education. Those influenced by their time in 1960s-70s Yorkville include cyberpunk writer William Gibson.

Today, some of the city's most exclusive retail stores line its streets, including Burberry, Lux Spa, Prada, Gucci, MAC Cosmetics, Hugo Boss, Chanel, Hermès, Louis Vuitton, Holt Renfrew, Tiffany & Co., Escada, Ermenegildo Zegna, [[Cartier SA]|Cartier], Harry Rosen, Calvin Klein, Cole Haan, Vera Wang, Lacoste, Ferrari, Maserati, Rolls-Royce Motor Cars, Williams-Sonoma, Bang and Olufsen, Betsey Johnson, Max Mara, Montblanc, Bulgari, Birks, Coach, Guerlain, Swarovski, and other upscale designer boutiques. The Holt Renfrew store on Bloor is the luxury retailer's flagship and largest store with 4 floors and various boutiques. Many flagships of other companies are located here as well, such as Harry Rosen, Town Shoes, Lacoste, Gucci, Coach, and Chanel (in which the Canadian flagship became one of the largest in the world.)

Yorkville is known for upscale shopping, restaurants, and the first five star hotel in Canada, becoming an excellent place for celebrity-spotting, especially in the Hazelton Lanes shopping complex. Yorkville still remains the top celebrity hangout in Toronto, and celebrities are seen throughout the year.

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