From Tom Brady’s Watches to Bogart’s Oscar: The 10 Most Glamorous Lots This Auction Season

The sales closing out 2024 are a collector's dream, including the Bob Mackie dress Miley Cyrus wore at the Grammys, a collection of Grace Kelly's letters, and cinema's most iconic pair of shoes.

No matter whether your tastes tend toward Hollywood’s golden age or Broadway legends, sports history or high-end timepieces, the winter 2024 auction season is particularly rich in glamour, offering collectors a chance at snagging some truly museum worthy pieces.

High-wattage lots set for sale before the end of the year at five global auction houses include everything from a Bob Mackie dress Miley Cyrus wore at February’s Grammy Awards to a variety of watches owned by Tom Brady and the best actor Academy Award Humphrey Bogart won in 1952 for The African Queen. “Just as it is in Hollywood, the auction scene is abuzz with excitement over iconic pieces that epitomize glamour,” notes Martin Nolan, co-founder and executive director of Beverly Hills-based Julien’s Auctions, which is hosting “A Week of Hollywood Legends,” the latest sale in its partnership with Turner Classic Movies, set for Dec. 10-13. The offerings range from Mackie’s designs and sketches for Cher, Carol Burnett and others to pieces from the estate of Sir Laurence Olivier and Dame Joan Plowright. Adds Nolan, “These artifacts not only represent iconic moments in film history but also reflect a broad spectrum of beloved cinematic genres and eras, appealing to diverse collectors, prestigious museums and investors.”

Among the lots increasingly sought after not only by collectors, but also for interior-design purposes, are the costume sketches produced throughout Edith Head’s prolific career. The legendary designer famously hired assistants to handle her sketching duties — Mackie was among those who took on the role when Head hired him in 1961 — but that detail is secondary to fans of her work. “Edith Head sketches have become much more popular on the market — not just among Hollywood collectors, but also for display in walk-in closets, bedrooms and bathrooms,” explains Peter Costanzo, specialist at New York-based Doyle Auctions. “We love selling Edith Head drawings because they’re beautiful and have a lot of movement, and her sketches of Grace Kelly [designs] always seem to perform well.”

The lots in Doyle’s upcoming Stage & Screen sale a group of sketches that includes two highlighting gown designs for 1955’s To Catch a Thief, the Alfred Hitchcock classic starring Kelly alongside Cary Grant. Neither design is seen in the film, but the sketches, which carry estimates of $5,000 to $8,000 each, still are expected to do well, Costanzo adds. And at a December 7 Hollywood/Entertainment sale presented by Heritage Auctions in Dallas, no less than six Edith Head sketches are on the block — from her work in films including Rear Window and Sabrina, both from 1954 — confirming the current interest.

Whether purchased for in-home display, to be secured in a safe or donated to a museum, here’s a look at 10 glamorous lots already attracting an abundance of interest.

When the iconic actress first moved from her native Philadelphia to New York City, she roomed at the Barbizon Hotel for Women during her early days as a model and actress, and there she met Prudence “Prudy” Wise Kudner, who became a lifelong friend. Over the ensuing years the two women corresponded often, and the result is a substantial collection of letters, telegrams, photos and other items Kelly sent to Kudner between 1948 and 1968. “It’s a really remarkable archive and covers all the time between Grace’s early successes through her time as princess of Monaco,” Costanzo says. “There are great letters from when she was in Africa filming Mogambo, for example. And one strain that goes through her early letters is telling Prudy about her constant trail of suitors, including her short-lived engagement to the designer Oleg Cassini. We know that Grace lived a very rich life, but the details seen in this correspondence is quite revealing, also because I’m not sure her biographers were aware of this material.” Included in Doyle’s Stage & Screen auction running through November 17, the collection carries an estimate between $60,000 and $80,000. (Update: The collection sold well above its estimate, for $165,600, including buyer’s premium.)

When the iconic actress first moved from her native Philadelphia to New York City, she roomed at the Barbizon Hotel for Women during her early days as a model and actress, and there she met Prudence “Prudy” Wise Kudner, who became a lifelong friend. Over the ensuing years the two women corresponded often, and the result is a substantial collection of letters, telegrams, photos and other items Kelly sent to Kudner between 1948 and 1968. “It’s a really remarkable archive and covers all the time between Grace’s early successes through her time as princess of Monaco,” Costanzo says. “There are great letters from when she was in Africa filming Mogambo, for example. And one strain that goes through her early letters is telling Prudy about her constant trail of suitors, including her short-lived engagement to the designer Oleg Cassini. We know that Grace lived a very rich life, but the details seen in this correspondence is quite revealing, also because I’m not sure her biographers were aware of this material.” Included in Doyle’s Stage & Screen auction running through November 17, the collection carries an estimate between $60,000 and $80,000. (Update: The collection sold well above its estimate, for $165,600, including buyer’s premium.)