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October 5th, 1962, 50 years ago, Dr. No debuted in theaters introducing us to author Ian Fleming’s greatest creation, James Bond.

Bond and his pension for fast cars, suave attires, and beautiful women seems like an overly manly wet dream but the character has prevailed and remained iconic in my eyes for its institutional appeal that for at least thirty years ran rampant with its Cold War history. It also helped that every decade saw a change in tone to fit with what people were going to see. In the sixties everything was grand and epic so Bond was the same, in the seventies it was flashy and over the top as a way of counterbalancing the serious auteur nature of the decades biggest films, the eighties it was neon camp, and in the nineties it was the blockbuster era of film. Today, Bond remains a balance to all of that and its realistic style mixed with the character’s famous hallmarks has made Bond profitable to a new audience and memorable to those who grew up with him.

When we think of James Bond, we think of the tux. Over nearly four decades, more than five men have worn formalwear with the ease of a t-shirt, each adding their own edition of the classic. Time has passed: Cuff links, cummerbunds, and studs have been added and removed, and it’s Bond’s tailored looks that still stand out. But the tuxedo is just the beginning of that. In more than 20 movies, we’d venture the iconic character has gone through more costume changes that any other film star. From that, there’s much to learn. But let’s start with five iconic looks, all from different Bonds (and eras), that you should add to your wardrobe now — as soon as you master the tux, of course.

It’s also important to remember how iconic he became just from how his first persona was portrayed. Sean Connery is still the definitive Bond and set a tone that one would argue has been difficult to match. Armed with a cool demeanor, a Walter PPK, and a plethora of dark humor, Connery’s Bond was as stealth as he was physical which is a pedigree at best on how to play the character. James Bond was the closest thing to a superhero that you can believe could exist and even had his own super suit by simply wearing a tuxedo or a tailored suit from Seville Row. Connery was the perfect post-WW2 Bond, carrying himself just like a combat veteran operating in the murky ambiguity of the Cold War. The man who defined the role also had a particularly strong era with which to wear suits: From 1962 through 1971, Connery proved over and over that a suit should be worn everyday of a man’s life. No matter the weather, look for something that’s slightly textured (like this charcoal masterpiece), then ground it with a dark knit tie and crisp white shirt (don’t forget the matching pocket square). Few things impress more than pulling off a three-piece. He was outdoorsy, tough, mouthy and unfailingly sexist. He was suave, gun totting, Brioni suit wearing, Bollinger Champagne drinking, smart, charming, witty personality that has paved the way for spy movies in Hollywood.

When Connery left the role the task was given to bring in an actor who could convey the same presence but with his own spin and sadly George Lazenby, whose only outing was 1969’s On Her Majesty Secret Service, couldn’t muster up a well mannered performance.  After returning briefly to Connery to keep the franchise afloat someone had to be put in a more permanent place and that fell to Roger Moore, who played Bond from 1973 to 1985. For all the cheesiness and quality issues of his period, Roger Moore did a good job of keeping the Bond character afloat during the 1970s and 1980s. Determined to not have him replicate Connery, Moore was slick, blow-dried, corporate, movie-star clean and pretty. He was perfect to represent the period from disco to the Reagan era’s faux tough-guys. As the seventies became the eighties, Bond became somewhat trendier: shirts unbuttoned a bit low, collars a tad wide. This being 007, of course, there were occasions to get dressed. And while neckties were sometimes absent throughout Moore’s 12-year-tenure, he went a step beyond the standard tuxedo. Take this cream dinner jacket, for instance, which would win any summer night when paired with black pants and slightly askew bow-tie.

As the world became far more real and the Cold War simmered, audiences closed out the eighties with two outings from actor Timothy Dalton as Bond in 1987 and 1989. Dalton physically could perform to Connery’s stamina but his Shakespearian background made him a far more profound Bond that didn’t necessarily fit the mold but it’s a testament that he is still regarded as one of the best actors to play the part even if he isn’t necessarily the most remembered Bond.  If a man is channeling James Bond, he’s likely already in tailored clothing daily. But that doesn’t mean a tie is always necessary — even for someone who’s technically employed by the government. Dalton’s Bond may have been the most serious — and his lapels the widest — but there’s a rakishness that comes through when you forego the tie and let your hair grow a bit loose. Note that if you carry a gun, people will undoubtedly still take you seriously, even in this more casual spin on suit dressing.
His successor, Pierce Brosnan on the other hand I still believe summed up all the best elements of his predecessors even if the quality of the films’ took a decline.

Brosnan’s first outing, is still a smashing explosion of action, sex, and political thrill but his three subsequent outings tended to lean more towards the hokey tone of the latter day Moore films. Brosnan was smooth, implacable, brilliant. The personification of a New Millennium, Internet start-up, computer-nerd’s wet-dream spy.

Daniel Craig for some may seem too serious but when you convey someone who is basically a young killer like Bond, you need that intensity but thankfully Craig also has charming good looks and a physique that can take the punches and dives off cars and trains that are needed to get the job done. Sure, Craig often wears a suit as 007. But these are modern times. And like other Bond’s before him, the actor has successfully proven that you can wear sportswear and still look sharp.
Daniel Craig’s Bond cruel, violent, heartless, inhuman, a thug. In truth, the perfect Bond for today’s world.

There is a slew of iconic imagery from this franchise ranging from the first appearance of an Aston Martin as Bond’s car of choice to the first time the man orders a traditional “shaken, not stirred”Vodka Martini.

For me Bond has never been a more entertaining character to spend some time at the movie theater with.