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

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 sketches produced throughout Edith Head’s career to illustrate her costumes. The legendary designer famously did not create the sketches herself, but that detail doesn’t matter 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 include two sketches 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.

Grace Kelly Collection of Letters

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.

Jerry Herman Yamaha Grand Piano

Jerry Herman — the legendary Broadway composer and lyricist, who created Hello, Dolly!, Mame and other beloved musicals — died in 2019, and now a variety of items from his estate have arrived at Doyle for auction. That includes the Yamaha Model C7 ebonized grand piano he owned since 1995. “It’s wonderful to have this, because as we have found while putting the public exhibition together, Mr. Herman has some ravenous fans,” Costanzo says. “He would have sat at this piano, sussed out ideas, sang songs at parties, because he loved to entertain, so you feel like you’re touching greatness. We’ve had a lot of interested parties, but it is a grand piano, the largest piano you can get, so it’s quite a commitment to Jerry Herman.” Also included in the Stage & Screen auction, all proceeds from sales of the piano and roughly 100 lots from Herman’s estate will be donated to the Jerry Herman Legacy Programs at the ASCAP Foundation, which funds music education via scholarships and other programs.

Elizabeth Taylor Cleopatra Costume

Propstore’s four-day Entertainment Memorabilia Live Auction, taking place in London through Nov. 17, includes a selection of costumes worn by Elizabeth Taylor in 1963’s Cleopatra, among the most talked-about films in the screen icon’s career. Directed by Joseph L. Mankiewicz, the epic film was famously beset with problems, including a case of pneumonia that put Taylor’s life in peril, but it was also on that movie set that the actress met Richard Burton, who would become her fifth husband (and her sixth, as the couple divorced in 1974, only to remarry the following year). While Taylor’s costumes today are considered wildly anachronistic, the trio behind all the film’s sartorial looks — Irene Sharaff, Renié Conley and Vittorio Nino Novarese — took home the Academy Award for best costume design, among four Oscar wins among nine nominations. This look worn by Taylor is seen toward the end of the film while Cleopatra holds Burton’s Marc Antony as he’s dying; it carries an auction estimate in US dollars of roughly $12,700 to $25,400.

Marilyn Monroe Photograph by Bert Stern

Also included in the Propstore event is “Marilyn Monroe in Black Dior Dress,” a pigment print by famed photographer Bert Stern. Part of a 1962 photo shoot that took place at the Bel Air Hotel just six weeks before Monroe’s death, the print is one of 2,500 images in a series known as “The Last Sitting” and is notable for its more elegant and introspective look and attitude, vs. the “bombshell” images at the heart of the actress’s public persona. With its frame, the print measures 30.5 x 26.75 inches and is inscribed by Stern both with his signature and “Marilyn.” More than six decades after her death, Monroe remains hugely popular among film and pop-culture fans alike, with Kim Kardashian among the better-known collectors of items associated with her. The auction estimate on this print ranges from roughly $6,350 to $12,700 in US dollars.

Tom Brady-owned IWC Pilot’s Watch Top Gun Edition

The NFL Hall of Fame retired quarterback and current Fox Sports NFL analyst made news in early October with the announcement that he would auction off a selection of personal items for the first time. The event, christened “The GOAT collection: Watches & Treasures from Tom Brady,” will be held at Sotheby’s New York on Dec. 10, with an exhibition of its lots open to the public Dec. 5-10. In addition to a range of football memorabilia, including the jersey Brady wore while running the 40-yard dash at the 2000 NFL Combine and a game-used helmet he wore while playing for the Tampa Bay Buccaneers, he’s also putting a selection of watches he’s worn over the years. A known timepiece collector, Brady is including this IWC Pilot’s Watch Top Gun Edition in the sale; the automatic chronograph features a 44.5mm black ceramic dial on an olive textile strap, one of 1,500 such pieces from a 2020 limited release. The watch carries an auction estimate between $5,000 and $10,000.

Tom Brady-owned Audemars Piguet Royal Oak “The Roast”

The Brady auction features 20 timepieces from coveted status brands that also include Rolex, Richard Mille, Patek Philippe and Audemars Piguet. From the latter comes the design that will cap the event, a unique piece custom-crafted for the superstar that he wore at The Roast of Tom Brady, which aired live on Netflix in May. For an interview appearing in Sotheby’s eponymous magazine, Brady recalled that Audemars Piguet CEO François-Henry Bennahmias texted him “out of the blue” one day, saying he wanted to create a one-of-a-kind watch that could be a collaboration between the NFL great and Michael Friedman, the Swiss brand’s designer. The result is a Royal Oak crafted in 18-karat white gold, featuring a 41mm case that houses a flying tourbillion and a salmon-hued dial, with “Tom Brady” spelled out in baguette-cut diamonds to form the indices. The watch carries an estimate of $400,000 to $800,000.

Edith Head Roman Holiday sketch

In addition to the pair of Grace Kelly sketches featured at the Doyle auction, Julien’s will include an Edith Head sketch in its December sale, highlighting an illustration of a costume design worn by Audrey Hepburn in 1953’s Roman Holiday, Hepburn’s breakout role. In the last scene she wears the white daytime dress depicted in this sketch, which Head inscribed to the actress and signed. Head won the Oscar for best costume design for a black-and-white film for Roman Holiday, while Hepburn captured the trophy for best actress (a subsequent lot is a photo of Hepburn holding her Academy Award). This item is estimated to fetch between $6,000 and $8,000.

Miley Cyrus Performance-Worn Bob Mackie Dress

Among the most exuberant moments at February’s Grammy Awards was Miley Cyrus’s performance of “Flowers,” minutes after she won the trophy for best solo pop performance, causing the singer to ad-lib mid-song, “I just won my first Grammy!” Among the five looks she wore that night, for her “Flowers” performance Cyrus wore a costume Bob Mackie designed as part of a 2002 collection that paid tribute to Broadway musicals. The beaded, fringed dress features a bare midriff and was chosen by Cyrus’s stylist, Bradley Kenneth. The look is among a healthy selection of costumes and sketches by Mackie at the event, including several pieces designed for Cher, which Nolan confirms are a highly anticipated element of the sale. “These pieces capture the spirit of Mackie’s boundary-pushing, glitzy designs that helped define Cher’s image over decades,” he says. Cyrus’s dress requires a starting bid of $4,500 and is estimated to garner between $6,000 and $8,000.

Humphrey Bogart’s Academy Award for The African Queen

His performance as Charlie Allnut in 1951’s The African Queen resulted in the only Academy Award Humphrey Bogart would win during his legendary career. More than 70 years later, the statue will be sold at the Heritage Auctions Hollywood/Entertainment sale set for Dec. 7 in Dallas. As it was Bogart’s only win out of three nominations — the other two were for 1942’s Casablanca and 1954’s The Caine Mutiny — film fans are hoping that, regardless of the buyer, this trophy eventually will find either a permanent or temporary home at the Academy Museum, which currently exhibits the Oscars won by Clark Gable and Sidney Poitier, among others. Bogart’s best actor trophy has a starting bid of $250,000, with no estimate listed, making it among the most-anticipated lots in the Heritage event.

Screen-matched Ruby Slippers from The Wizard of Oz

They’re the most famous shoes in cinema, perhaps in history. Even though L. Frank Baum described the shoes worn by Dorothy Gale as silver in his 1900 book The Wonderful Wizard of Oz, MGM studio head Louis B. Mayer decreed that the slippers needed to be red for his 1939 production of the story, as every corner of the screen in the Victor Fleming-directed film needed to showcase the Technicolor film process that was still in its infancy. Costume designer Adrian conceptualized low-heeled pumps crafted in red silk faille and fully embellished with crimson sequins and topped with small bows — and depending upon whom you ask, up to seven pairs were created for star Judy Garland to wear. They were made by the Innes Shoe Company, which once resided at the corner of Hollywood Boulevard and Wilcox in Hollywood.

Four pairs are known to have survived, with one pair ending up in the hands of a fan who took them on a touring exhibition that included the Judy Garland Museum in the star’s hometown of Grand Rapids, Minn. But in 2005, those slippers were stolen from that museum. Fast-forward 13 years, and a 2018 tip led the FBI to locate and retrieve the stolen shoes, which were soon authenticated by the Smithsonian Institute’s National Museum of American History, the home of one of the other three known pairs. In 2012, meanwhile, a consortium that included Steven Spielberg and Leonardo DiCaprio purchased one of the other pairs to donate to the Academy Museum. Fold all those facts together, and it’s little wonder that the ruby slippers slated for auction Dec. 7 already carry a current bid of $812,500 (more than $1.015 million with buyer’s premium). With no estimate listed, film fans and museum specialists alike will be keeping an eye on the hammer price for one of Hollywood’s most famous and historic items.