In the 1980s James Bond returned to his roots after over a decade of more fantastic stories. Roger Moore left behind his flashy clothes of the 1970s and had a new wardrobe of more traditional clothes for the 1980s. Though he didn’t wear them, trilby hats were a consistent part of this new wardrobe.
In all three of Roger Moore’s Bond films of the 1980s—For Your Eyes Only in 1981, Octopussy in 1983 and A View to a Kill in 1985—Bond enters Moneypenny’s office near the start of the film holding a trilby. Never is he wearing the hat; it is merely a prop to toss or place onto the coat tree in the office as a throwback to Sean Connery’s entrances in the 1960s Bond films.
Bond’s trilby is a classic English felt hat with a tapered crown and short brim that is sharply turned up at the back. It is like a fedora but with a slightly different shape, not the cheap straw or wool hats commonly worn over the past decade on the back of the head that have given the trilby a bad name today.
The trilby was an iconic part of Bond’s look in the 1960s, appearing in every Bond film of the decade. It appears in every opening gun barrel sequence from the start of the series through 1971’s Diamonds Are Forever, whose gun barrel was originally filmed for Thunderball in 1965. Bond’s first appearance on screen is in Dr. No‘s gun barrel in the form of a trilby-wearing silhouette. It was not Sean Connery in this sequence but instead stuntman Bob Simmons. We can’t see Bond’s face, but we see the trilby, which is the first identifying item of Bond’s look. Lazenby wears a trilby in his gun barrel as well to start off the tenure of a new Bond actor with this familiar silhouette.
When Roger Moore became Bond with 1973’s Live and Let Die, the trilby was long out of fashion, and Bond no longer needed to be identified as a hatted silhouette in the gun barrel sequence. It was one of the many ways Moore distanced his Bond from Connery’s. By the time the 1980s arrived, Moore was well-established as Bond, but the film series needed to bring itself back to its origins after straying so far from them in the 1970s. Bringing back the trilby was one way Bond returned to his origins.
The hat is a symbol of the past, a status it first achieved in the early 1960s and one that firmly took hold by the end of the decade. In 1981 Bond would have looked too old-fashioned had he worn a trilby. But he could carry it into the office as a callback to the past, to show that a more traditional Bond has returned without looking like he belongs in the past.
It is difficult to imagine Roger Moore wearing a trilby. He wears a reversible cap in Octopussy and top hat in A View to a Kill, but both look like costume on him. The only headgear Moore looks comfortable in as Bond are the knit caps he wears for skiing. When James Bond was wearing trilbies in the 1960s, Roger Moore was showing off his pompadour throughout the decade in The Saint.
Moore’s 1960s pompadour would never have survived under a hat, even with all the hairspray. His 1980s pompadour wouldn’t have done any better, which is possibly another reason why he walks into the office holding the hat rather than wearing it. Moore’s hair always had to look perfect. His flatter hairstyle in the 1970s worked better with hats, such as the bowler hat in The Man Who Haunted Himself, the film that debuted his less voluminous 1970s hairstyle, and the deerstalker in Sherlock Holmes in New York.
Roger Moore’s trilbies are similar to Sean Connery’s with a narrow brim turned up at the back, a tapered crown with a front pinch and centre dent, and a thin grosgrain ribbon at the base of the crown.
The trilby in For Your Eyes Only is navy to match his suit, and the grosgrain ribbon is also navy. The trilby in Octopussy is dark grey with a black grosgrain ribbon. The trilby in A View to a Kill is a muted brown, and while the grosgrain band is not visible, the hat is revealed to have a brown leather sweatband and a white lining inside. Most trilbies are unlined for a more informal feel.
Not hatter has confirmed where Moore’s trilbies came from. Lock & Co., Bates, Christys’ and Laird are the main hatters still around today that could have provided the hats. It is difficult to identify the hats from the films because little of them is seen on screen, with only Octopussy providing a good shot of the hat. The hat in Octopussy appears to be a match for the Lock & Co. Voyager rollable trilby in grey, which has a fairly narrow 5.5 cm brim. The trilby in For Your Eyes Only has a similar profile and may be the same hat in navy, but no detailed shots of the hat are available.