Jenner posed for a series of stunning photographs by legendary photographer Annie Leibovitz.
The glam squad behind Jenner's classic beauty and Old Hollywood style included stylist Jessica Diehl, makeup artist Mark Carrasquillo, hairstylist giant Oribe, and celebrity manicurist Deborah Lippmann.
"I didn’t want her to look like a man in a dress. I wanted her to look like a beautiful 65-year-old woman," makeup maestro Mark Carrasquillo told Vanity Fair.
Carasquillo created a soft makeup look without the contouring much-loved by the Kardashian clan.
The eyebrows were filled in with Estée Lauder Stay-in-Place Brow Lift Duo in Soft Brown, lashes were coated with Estée Lauder More than Mascara in Rich Black and a few individual mink falsies were applied. Very little eyeshadow was used, followed by a flick of Tom Ford Eye Defining Pen in black along the top eyelid.
For Jenner's elegant-yet-natural hair, Oribe looked to Cindy Crawford for inspiration, explaining: "I wanted to create a glamorous look that I normally do for any woman, and sexuality was very important in this context."
Manicurist Deborah Lippmann was the first professional nail artist to work on Jenner, as she always did her own.
For the cover shoot, Lippmann filed Jenner's natural nails (no extensions here!) into an almond shape and used her range's signature deep red polish Lady Is a Tramp.
Vanity Fair's fashion and style director Jessica Diehl revealed the shoot was inspired by Hollywood stars like Lauren Bacall, Faye Dunaway in The Thomas Crown Affair and even Jackie Kennedy.
Diehl said of Jenner in Vanity Fair: "She has a pretty good idea of what makes her feel good, and those are classic silhouettes."