The 69-year-old Motown icon sported a rather unflattering baggy blue tracksuit, beige Ugg boots and black bag.
Once something of a sex symbol when she found fame with The Supremes in the 1960s, she was clearly content to stroll to the grocery in her loose-fitting getup.
Diana's journey to stardom has become part of a hit Broadway musical production, which premiered last Sunday in New York.
The Musical chronicles her road to fame along with some of her fellow icons from the late 50s and 60s.
The play tells the story behind the groundbreaking genre of music - pioneered by singers like Diana - that hit the airwaves in 1959, produced by record label Motown.
The story centres on Diana and Motown visionary Berry Gordy as they fought against the odds to create a new sound that would come to dominate the charts through the 1960s and 1970s.
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