Bennett has six children: one daughter Cleo (born 1988), from her first marriage, and five sons: Peik (born 1996), Truman (born 1999), Pierson (born 2002), Larson (born 2003), and Finn (born Dec 1, 2006), whom she discovered she was pregnant with while competing on "Project Runway", with her late husband, architect Peter L. Shelton. On August 26, 2012, Shelton died of cancer in their New York home. Shelton's work as a co-founder of Shelton, Mindel & Associates, and a memorial to him was in the November 2012 issue of Architectural Digest.