The original Valley Fair Shopping Center, opened in 1958, was confined to the eastern side of the property in San Jose.

At the western side was another outdoor shopping center, Stevens Creek Plaza in Santa Clara.

[8] Nordstrom was extensively remodeled, adding two new restaurant concepts and a completely revamped store design.

[6] The mall's lower level Nordstrom wing was reconfigured into a "Luxury Collection", with new luxury tenants like Mulberry, Saint Laurent Paris, Bottega Veneta, Versace, Giorgio Armani, Tory Burch, Salvatore Ferragamo, and Prada joining existing tenants Louis Vuitton and Tiffany & Co.[9] In 2012, San Jose raised its minimum wage to $10 USD an hour, but Santa Clara did not, leading to what the NPR Planet Money team dubbed "A Mall Divided," where workers on one side of the mall were being paid $2 less than the other side.

[12] The mall's prosperity came at the expense of San Francisco's Union Square and its sibling mall Westfield San Francisco Centre to the north, which lost many retailers who either moved to or preferred to remain operating in Northern California only at Valley Fair.

[12] In 2007, Westfield announced major expansion plans which would increase the gross leasable area to over 2,000,000 square feet (185,806.1 m2), adding anchor stores Bloomingdale's and Neiman Marcus, 100 shops, and a 3000 space parking structure.

[15] In early 2015, Westfield unveiled a new proposal for a $1.1 billion expansion, which called for the addition of a three-level 150,000-square-foot (13,935.5 m2) Bloomingdale's department store,[16] a Showplace Icon luxury cinema,[17] and the addition 500,022 square feet (46,453.6 m2) of new interior shop space, adding over 100 new stores,[3] including an outdoor restaurant collection fronting Stevens Creek Boulevard, and 3,000+ new parking spaces.

[18] The expansion and Bloomingdale's had its grand opening on March 5, 2020, creating a third interior thoroughfare and an outdoor dining district.