Clothes and fashion played a central role in the 1960s countercultural revolution in the United States and at the center of the counterculture’s fashion in the Boston-area was Krackerjacks. Krackerjacks was founded in Cambridge, Mass. by Donald "Jack" Levy and Alan Peterson in 1966 and was a boutique synonymous with "mod" and "hippie" fashion and accessories. In 1967, when Krackerjacks was attacked, among other shops, for having "obscene" buttons by Cambridge City Council member Thomas H.D. Mahoney, it became a symbol of the countercultural movement itself. Levy fought back against the ban, refusing to take the buttons off his shelves despite pressures from local police. Krackerjacks survived and expanded into a successful franchise.

In addition to Karckerjacks, Levy opened several other boutiques in the Boston-area: Garbo, a women's clothing store; Dazzle in 1971, a vintage clothing store; and Goods in 1976, a natural fiber and novelty store. In 1986, Levy expanded into the restaurant business, purchasing and refurbishing the Blue Diner (now the South Street Diner and no longer owned by Levy). He currently owns the Deluxe Station Diner, the Deluxe Depot Diner, and the Deluxe Town Diner in Newton, Framingham, and Watertown, Mass. respectively.