Robert Oliver received his degree in architecture from the University of Illinois in 1950, he spent a brief time in Boulder, and then Grand Junction, where he interned to get his license. With his wife, moved in Aspen, prior to 1953. He worked as an independent architect from 1956, generally from home. Roy loved the design process, appreciated Richard Buckminster Fuller and Frank Lloyd Wright, and attended the summer international design conferences at the Aspen Institute.Mostly Roy's Aspen work dates from the 1950s into the 1970s, since, on 1975, he moved to Paonia, Colorado.

Aspen buildings

A numerous of Aspen buildings are attributed to Roy, including the Mountain Chalet, Snowmass Mountain Chalet, Prospector Lodge, The Heatherbed, and Cortina Lodge, and residences for Friedl Pfeiffer and Edgar and Polly Stern, the latter structure universally admired. He designed his family's house on Castle Creek. Roy designed the multi-family modern chalet at 608 W. Hopkins Avenue (1962), the modern chalet for Pietro and Dorothy Danieli at 232 McSkimming Road (1963), and the shake-shingled, dramatically mansarded multi-family at 700 W. Hopkins Avenue (1968).