Sean Connery’s Bond is well known for his trilby. It has been said that the original hats came from James Lock & Co. Hatters on St. James Street in London, but the style can still easily be found from most English hatters. The trilby is a felt hat with a narrow brim. The brim is usually only about 2 inches wide—or slightly narrower—and sharply turned up at the sides and back. The brim is finished with a raw edge. The crown is short with a centre dent at the top and a pinch at the front. The grosgrain band at the base of the crown is narrow (roughly a half-inch wide) and matches the colour of the hat. The example above from Dr. No was dark grey-brown (which looks green on the Blu-ray in some shots), with the grosgrain band in a slightly lighter tint.
In From Russia With Love, Goldfinger, and Thunderball he can be seen with another dark brown trilby, but Lock can only confirm they provided the hat for Dr. No. The closest hat to what they sell now is the Sandown model, though the Sandown’s brown looks lighter and warmer than Connery’s. Connery can last be seen carrying a trilby in You Only Live Twice. George Lazenby wears black and navy blue trilbies in On Her Majesty’s Secret Service, but his navy hat has a wider grosgrain ribbon. Connery wore his with either suits or blazers whilst Lazenby also wore his with a dinner suit and his wedding attire. Roger Moore brought back the trilby in the 1980s though he never actually wore one, only throwing his on the rack when entering the office.