Although the idea of James Bond and masculinity has gone on quite the wild adventure since Sean Connery’s initial depiction of 007 in 1962, one consistency remains, regardless of which actor plays him—his suave attire and fashion.

The first ever introduction we get to Bond on screen is Connery sitting in a casino in Dr. No, exemplifying the sort of artistic license and wild good fortune the character often finds himself in during high-pressure casino games.

Part of Bond’s entire look is the energy and vibe he brings to the table; with this good fortune, his look might not have the same sort of impact if he was having bad luck at the table rather than the perennial good luck he often finds himself having.

The Modern Day Bond Look

Daniel Craig’s last outing as James Bond ended an era that began with Casino Royale in 2006. There’s not much debate about the iconic scene from that film, which is the high-stakes poker match that takes place and ends up having a 9-figure prize pool.

Bond and casinos are synonymous with each other, and although the world has shifted collectively toward digital casinos, the suave mystery and enigmatic charm of James Bond and his gambling techniques are something we expect to see in the upcoming films. We can’t imagine Bond will shift to online gambling like so many of us. It would probably be slightly out of character, meaning he’d not need to iron his tuxedo.

While the popularity of online casinos and gambling has exploded over the years, it hasn’t taken much away from the casino charm that Bond has with his fashion choices. His gambling skills  continue to be a staple of his character, which is likely to remain the case even post-Daniel Craig.

Tuxedos & Suits

Wearing a tuxedo every time you go to the casino isn’t our advice, either. There’s definitely a time and a place to show off your suaveness. Bond’s charisma and charm are derived from his personality and sharp wit; his attire is just an extension of that.

Connery, Pierce Brosnan, Roger Moore, and Timothy Dalton all wore sharp-fitting tuxedos when they portrayed Ian Fleming’s legendary spy character. While Brosnan didn’t stray too far away from the casino tux, he had many eye-catching styles in the four films where he depicted 007 (GoldenEye, Tomorrow Never Dies, The World Is Not Enough, and Die Another Day.)

If the Bond casino look is slightly out of your price range, just like it is out of mine, some of the other more casual designs adorned by Pierce Brosnan could be a more likely addition to your wardrobe. Danie Craig’s gold-lapeled brace shirt that underpinned his tuxedo look in the crunch poker game in Casino Royale is definitely high up there for the most fashionable Bond.

Comparing tuxedo styles can help you boil down the look you want – and while we might not all have the flex and charisma to swan around looking like Pierce Brosnan or Daniel Craig, it’s still a sharp look.

Ranking The Most Fashionable Bonds

Roger Moore, Timothy Dalton, and George Lazenby didn’t do a bad job as Bond, but time has not been kind to their fashion choices. While they definitely weren’t the worst dressers of their era, there’s a two-tier ranking for ranking the top Bond fashionistas.

Daniel Craig has the advantage of being the most recent Bond, so a lot of the fashion in his films hasn’t had to deal with the fashion acid test of time. Although some questionable shirt choices in Casino Royale mean he sits just behind Brosnan in the fashion stakes.

Even the most ardent Bond fan would struggle to make a case for any Brosnan film being up there in the higher echelon of the Bond library. It’s more of a challenge to rank the least forgettable of his films rather than the quality. However, his suave suits, linen trench coats, and a more refined, sensible business look definitely suited Brosnan.

While some rank Connery behind Craig – we’re not going to. In our humble opinion, Connery’s selection of films eclipses Craig, as does the towering Scot’s fashion as he portrayed 007. In fact, we’d probably go as far as saying he is the quintessential image of Bond fashion.

Final Thoughts

Lazenby always gets the short straw regarding Bond rankings, and Daniel Craig seems to be riding the crest of a wave following his successful 15 years as the man himself. However, for us, Connery is the clear winner of this one.

His suaveness, delivery, and overall look as Bond are why the films are cited as a springboard for the subsequent success. While there were other factors, of course, such as the world-famous theme and the quality cinematography of many of the early films, Connery’s performance and fashion added even more layers and set the tone for the decades of success, which turned Bond into one of the most profitable film franchises ever made.