It’s hard to remember a time when fashion and beauty commentary were not ubiquitous. When red carpet pre-shows for the Oscars or the Met Gala were not the norm, or before anyone with a TikTok or Instagram account could be an obsessive pundit on celebrity style.

Steven Cojocaru was there, however, at the beginning of this sartorial saturation. The Canadian writer and TV host, now 50, hustled tirelessly in his early career to get legacy media to take style as seriously as he did. He became People magazine’s first West Coast fashion editor in 1997 and was the first out gay fashion correspondent for NBC’s “Today” during the highly watched Matt Lauer and Katie Couric era.

His persona was so vivid that Jimmy Fallon parodied him on “SNL” in 2001. His exacting analysis of winners and losers in the high-stakes game of celebrity dressing was equally loud and memorable. But decades ago,...