Chess King was a United States men's clothing retailer created by the Melville Corporation. From its founding in 1968, it grew to over 500 locations by the mid-1980s, before an eventual decline, sale, and closure of the chain in 1995.

In 1967, traveling salespeople from Melville's Thom McAn shoe business noted a "wide open market" for young men's clothing, which gave birth to the idea of starting a young men's clothing and shoe store.^[1] Market research reportedly found that chess and auto racing were popular interests of young men.^[1]

The first Chess King branch opened in the Dedham Mall in Dedham, Massachusetts (just outside Boston), in March 1968.^[2] In 1970, The New York Times described the store's concept as "teen-male apparel dress shops whose stores are highly identifiable, with bold coloring and designs aimed at appealing to the 12-to-20 male market."^[2] Five additional locations were opened in 1968, and 21 more in 1969.^[2] By late 1972, it had already grown to about 150 locations.^[3] By 1978, it had 300 locations.^[1] And by 1984, it had grown to over 500 stores.^[4]

Chess King also experimented with three spin-off specialty stores in the late 1980s and early 1990s. The first, named "FreeFall", carried designer labels for men and women and was geared toward higher-end, designer, brand names. The second, named "The B Club", carried activewear for both men and women. The third, named "Garage", had a 1950s inspired decor along with a Nash Metropolitan automobile in most locations. The retailer was successful through the 1980s as a purveyor of wild 1980s fads and fashion,^[5][6] but changing fashion trends contributed to the chain falling on hard times at the beginning of the 1990s.^[5][6]

Melville agreed to sell Chess King in March 1993 to Maryland-based Merry Go Round Enterprises (MGRE),^[7] with the sale being finalized in May of that year.^[8] In January 1994, MGRE filed for Chapter 11 bankruptcy.^[9] In November 1995, the Chess King chain closed.^[10]