Investigating 55 years of the world’s most iconic man.

When he sat down to pen his first novel in the early 1950s, Ian Fleming could have hardly have known the lasting impact his creation would have on the world. Yet, more than five decades and 24 official films later, James Bond is inarguably an international institution. What’s the secret of this timeless character who became the subject of the longest continually running and fourth highest-grossing franchise in movie history?

“Timeless” may not be the first word that comes to mind when thinking of the James Bond series. The early films are marred with cringe-worthy and overtly sexist moments from Bond smacking a masseuse’s ass to scurry her away during “man talk” or a grateful gypsy settlement presenting Bond with two women.

Moments like that have aged as well as an avocado, but James Bond himself has remained one of the most influential style icons over the last five decades due to his head-to-toe timeless style. It’s a style that oozes through everything from his attire to his attitude and has followed every Bond actor since a tuxedoed Sean Connery first introduced himself in Dr. No.

55 years after that iconic introduction to movie audiences, luxury clothiers like Brioni, Tom Ford, and Turnbull & Asser have made the most of their association with James Bond. Even single-shot 007 actor George Lazenby recognized the importance of Bond’s clothing to his image, outfitting himself for his successful Bond audition in 1968 in a tailored suit that had originally been commissioned for Sean Connery and topped off with the Rolex Submariner that Connery had popularized with the character.

But as Lazenby proved, there’s much more than picking up a Savile Row suit and the right watch to reach that 007 level of sophistication, but the following fundamentals of clothing and confidence can lead you there without busting your wallet.

You could even consider it a formula, just as formulaic as the office banter with Moneypenny, the mission briefing from M, and picking up the gadget from Q before landing at the airport in some exotic locale. We’ve taken a hard look at the formula and distilled it down to practical advice you can use to crack Bond’s code to timeless and sophisticated style.

The first thing you’ll need on your mission to sophistication: a timeless suit.

1. A Suit That Fits

Some might argue that confidence comes easily to a man like James Bond as the six actors who have filled the role fall on the more handsome side of the spectrum, but Bond’s confident appearance comes from a balance of classic tailored clothing that works with his complexion and physique.

Sean Connery’s Bond essentially created a template for future Bonds to follow, more so than Bond’s literary creator Ian Fleming, who had a considerably less stylish and more idiosyncratic approach for his hero. Most unforgivably, Fleming outfitted his hero in short-sleeve shirts under his suits. That’s right…the literary James Bond could have traded style tips with your high school principal.

Fortunately, Terence Young, the stylish director of Bond’s first on-screen adventure, Dr. No, took the opportunity to craft Bond after his own image. Like Fleming before him, Young extended his own preferences to the character, outfitting him in suits tailored by Anthony Sinclair and “cocktail cuff” shirts by Turnbull & Asser.

When conjuring the 007 image, you picture Sean Connery confidently gliding across the screen in a well-cut suit expertly tailored for him by Anthony Sinclair, looking like a man who could belong as much in 2017 as he did in 1967. Connery projected the image of the prototypical Bond with his well-fitting suits that flattered his athletic physique and complexion, frequently in shades of gray and paired with pale blue shirts and navy grenadine ties.

Fashionable details can be incorporated to keep a suit looking fresh, but fashion should never influence a suit to the point of an unflattering fit. Instagram is littered with “gentlemen’s style” accounts featuring models bulging out of skin-tight suits with pencil-thin ties and, for some reason, plastic-looking loafers worn with no socks. No Bond costume designer would ever stoop so low as to put Bond in such a low-rent runway look, but that’s not to say that even 007 is totally immune to the fault of excessive “fashionable” influences.

Daniel Craig exemplified this in Skyfall when his otherwise beautiful Tom Ford suits were threatening to burst at the buttons and seams if they were fitted even one millimeter closer to his body.

On the other hand, Timothy Dalton was ill-served by his tenure as Bond in the late ‘80s when baggy was in, and he finds himself swimming through the expansive shoulders of his suits as frequently as he’s swimming among the sharks in Licence to Kill.

2. Classic Approach to Casual

Is it unfair that Roger Moore is often remembered for his safari jackets than the elegantly tailored suits of his 12 years as James Bond?

This unfortunate association for Roger Moore is indicative of the fact that trendy casual wear has the natural tendency to age more rapidly than suits. It’s okay and expected for a fashionable outfit to have trendy details, but if the entire outfit will end up as a comic time capsule, you’d be best to avoid it. Sure, the warm, tropical settings are the most appropriate situations for Moore’s safari jackets, but just because he can wear them, should he?

That’s not to discount the importance of situational context. Think of Pierce Brosnan in GoldenEye, leaping onto a yacht moored to the Monte Carlo coastline while wearing a dashing double-breasted navy blazer with glistening gold buttons and a French blue shirt, khaki trousers, and brown brogues. Certain details of the outfit – the trousers’ triple pleats and the blazer’s large fit – may have been trendy, but the overall outfit is timeless and it works because Bond looks like he belongs on that yacht.

From zoot suits and disco shirts to leisure suits and parachute pants, every decade has its fashion fads that invariably become the object of derision just a decade later. You could call it the “yearbook photo” effect. The trick, as the best-dressed Bonds have taught us, is to seek that classic approach that will translate well in any era.

Daniel Craig has restored a traditional sensibility to James Bond’s casual wear, evoking timeless icons of the ‘60s like Steve McQueen with Harrington jackets, cardigans, polo neck sweaters, and desert boots and Sean Connery’s Bond with polo shirts and khakis.

3. Dress for Your Surroundings

Ian Fleming’s James Bond was much less of a fashion plate than the character of the films, but he followed a basic sartorial formula that followed him through his literary adventures: a navy blue worsted business suit in the city and a “yellowing” houndstooth check suit in the country.

The cinematic Bond takes this concept further, diversifying his wardrobe to appropriately (and timelessly) fit into any setting. Bond’s frequent trips to the country find him sporting attractive, rugged, and sporty tweed jackets and suits with knit ties.

These rural adventures also find Bond exploring various interesting suiting patterns, such as the gun club check sport coat worn for his visit to the MI6 safe house in The Living Daylights.

For a few rounds of golf against Auric Goldfinger, Bond wears a classic and functional ensemble of a gray polo, burgundy lightweight sweater bearing the Slazenger logo, and brown kiltie loafers, the traditional golf shoes.

In warmer climates, Bond always looks cool and fresh. He may wear lighter weight and lighter colored variations of his standard gray business suit, as in Thunderball, or make use of the comfort and breathability of linen in his suits and casual wear.

4. Invest in good shoes – people will notice!

Good shoes are a worthy investment. They protect your feet, they can make or break your comfort for that day, and – most importantly for someone like Bond – they are almost universally noticed by women as an indicator of your status.

Ian Fleming had stipulated slip-on moccasins for his Bond, but filmmakers for the big-screen knew that this casual shortcut wasn’t going to fly if the character would follow Raymond Mortimer’s oft-misquoted maxim: “James Bond is what every man would like to be, and what every woman would like between her sheets.”

With his suits, Bond primarily wears black leather dress derbies and oxfords. It’s important to know the difference: the less formal derby shoes have open lacing, and the more formal oxfords (or balmorals) have closed lacing.

By the Brosnan and Craig eras, Bond was wearing a well-publicized arsenal of footwear from luxury brands like Church’s, Crockett & Jones, and John Lobb, wearing everything from boots and brogues to monk shoes and oxfords.

If Bond was in a situation that didn’t call for a luxury shoe, he still had just the right footwear. Vacationing in the Bahamas a la Thunderball? Canvas rope-soled espadrilles are a must. Preparing for desert combat? What better than a Steve McQueen-style desert boot?

5. Timeless Timepieces

“Rolex?” asked Vesper Lynd after catching a glimpse of steel around Bond’s left wrist. “Omega,” he clarifies with a smirk.

It may have been a moment of shameless product placement in Casino Royale, but it’s also a commentary on the importance of a good watch.

The emphasis on Bond’s watches is another aspect added by the films that wasn’t present in Ian Fleming’s original novels, where the only real mention of Bond’s timepiece was a Rolex Oyster Perpetual in On Her Majesty’s Secret Service that was quickly pummeled when 007 needed a quick “knuckle duster” to take out an enemy.

The best Bond watches are elegantly simple and versatile timepieces that reflect Bond himself: sharp as hell but ready for heavy duty work.

Audiences often remember Bond’s watches as explosive, laser-enhanced gadgets, but if their technological function was so important, than the Spectre team would have placed Bond in an Apple Watch… which, I assure you, would look just as silly 30 years from now as Roger Moore’s dated Seiko digital watches looked on him. (Sorry for the frequent abuse, Roger.)

Striving more for timelessness than tech innovation, Spectre’s team revisited one of the most popular watches in the Bond canon: Sean Connery’s stainless Rolex Submariner in Goldfinger, worn on a striped vinyl strap. The effect was updated to reflect the current Omega tie-in with the franchise, fitting a new Omega Seamaster 300 onto a true NATO strap with five black and gray stripes.

Of course, Bond’s luxury watches can cost thousands of dollars. Luckily, Primer’s got you covered when looking for that timeless look and feel of a vintage Omega without the pricetag.

6. Learn from Bond’s Mistakes

Yes, even 007 makes errors. Sure, you may have the right clothes…but do you know how to wear them?

We’ve talked about the ill-advised “trendy tailoring” that marred seemingly every Bond but Sean Connery, but Connery’s own inexperience with fine clothing frequently emerged on screen, even under the tutelage of the dapper Terence Young.

In his first and last official Bond films, Sean Connery makes the bush league mistake of buttoning both of his suit buttons, transforming his bearing from suave secret agent to amateur prom king.

Diamonds are Forever was a veritable tour de force of Connery Bond’s sartorial lows, with the one-two punch of wearing an immaculate white dinner jacket in a Las Vegas casino (better known for its sea of fanny packs and cargo shorts) and a heavy tweed jacket and turtleneck in the middle of the Mojave Desert. There’s also the issue of that short pink tie.

Fast forward to Daniel Craig, whose grittier approach to the character unfortunately accompanied a bolder approach to suiting up with flaws not limited to the fit. Vesper Lynd provided him with a beautifully tailored Brioni dinner jacket to look “like a man who belongs at that table” for the Casino Royale poker games, but his decision to remove his jacket to sling it over the back of a chair makes him look more like an immature groomsman who no longer belongs at a wedding.

By the next film, Craig’s Bond is drawing attention to his bespoke tailoring by often leaving one of his cuff buttons undone, signaling that his jacket has functioning buttons and thus wasn’t bought off the rack or as part of a Jos. A. Bank three-for-one deal. It’s a rakish affectation that may impress the “board room bros” but draws even more attention to the supposed “secret” agent, particularly with his excessive five-button cuffs in Quantum of Solace.

7. Attitude is Style

James Bond’s attitude sets him apart as more than just a well-dressed man. Even when stripped down to his skin in Casino Royale, facing a gruesome fate at Le Chiffre’s hands and without the armor of his tailored clothing, he’s still the confident 007 that tops the field of male aspirational figures, defiant in his unwillingness to mask his fear and dignified in his acceptance of the situation.

The character of James Bond has evolved through time, reflecting the societal concepts of masculinity from the unflinching and unemotional portrayal by Sean Connery to the nuanced, brooding character portrayed by Daniel Craig. Bond’s confidence has always been a defining characteristic, but his confidence evolves into a more validated trait by his acknowledgment of fear. When Sévérine, the ill-fated femme fatale of Skyfall, asks what he knows about fear, he responds with “all there is.” Yet, he persists, consistently meeting danger without blinking an eye.

Travis Pastrana, a real-life daredevil who regularly pulls off Bond-style stunts like jumping out of an airplane without a parachute, has acknowledged that far from being immune to fear, he acknowledges it and overcomes it with preparation, trust, and commitment. This level of situational readiness keeps Bond cool under pressure no matter what challenges his missions will bring.

“This may be hard for a blunt instrument to understand, but arrogance and self-awareness seldom go hand in hand,” Judi Dench’s M sagely warns Bond in Casino Royale. Arrogance is frequently the byproduct of overcompensation, so balancing self-awareness with self-appreciation delivers the confidence with which Bond carries himself and lives his life.

That’s not to say that Bond’s strong degree of confidence doesn’t overlap with occasional arrogance. He’s not above smugly correcting colleagues on the vintage on which a sherry is based, but when he does, he’s never wrong. Bond is aware of both his fear and his capabilities, and this self-awareness begets a degree of confidence as incorruptible as his dedication to queen and country.

How has Bond influenced your sense of style? Let us know in the comments below!