Screenshots, clockwise from top left: Sean Connery in Goldfinger, George Lazenby in On Her Majesty’s Secret Service, Roger Moore in Live And Let Die, Daniel Craig in Skyfall, Pierce Brosnan in Die Another Day, Timothy Dalton in License To Kill

Screenshots, clockwise from top left: Sean Connery in Goldfinger, George Lazenby in On Her Majesty’s Secret Service, Roger Moore in Live And Let Die, Daniel Craig in Skyfall, Pierce Brosnan in Die Another Day, Timothy Dalton in License To Kill
Graphic: The A.V. Club

James Bond is a man who’s all about the details. After nearly six decades on film, audiences have become well aware of his specific proclivities, from his preferred method of transportation to the way he likes his drinks prepared. Given his eye for the particular, it’s no surprise that 007 is also quite the snappy dresser.

Sean Connery’s debonair 007 set a high bar for style, but each successive actor has managed to put their own sartorial spin on the spy, threading in the trends of their respective eras while maintaining a certain timelessness that’s made Bond an icon, generation after generation.

But what can be gleaned from the wardrobe of the world’s most famous spy? If we read between the stitch-work of Bond’s signature looks, what do they say about the men who wear them?

For answers, we turned to menswear expert Sean Crowley, whose particular knowledge of British vintage menswear makes him well-suited (pun intended) to assess the film fashions that have come to define Bond since 1962. A former designer for Ralph Lauren, Crowley now operates a vintage shop of his own—Crowley Vintage & Antiques in Brooklyn, New York—that deals in “traditional menswear, soup to nuts.” Like many children of the ’80s and ’90s, Crowley’s own appreciation of 007 started with the semi-regular Bond movie marathons that would play on network television. He said he’s come to appreciate what all six actors have brought to the role, particularly how they’ve each shaped his sense of style to fit their own. (Though, for the record, Sean Connery’s his favorite: “He’s the exemplar, the quintessential Bond.)

As No Time To Die hits theaters this weekend—Daniel Craig’s final of five films, and the 25th in the official franchise overall—it felt like the perfect time to dive into the costume closet with Crowley and explore some of James Bond’s most notable outfits. With looks representing each actor, each era, and each style of 007 (there’s plenty of suits, of course, but also streetwear, tactical wear, and resort wear, too), our menswear expert surveys the evolution of style through the eyes of Bond.