(00)7 Secrets of James Bond’s Timeless Style

(00)7 Secrets of James Bond’s Timeless Style
Investigating 55 years of the world’s most iconic man.
(00)7 Secrets to James Bond's Timeless Style - 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.

James Bond wearing a tux in Dr No

The birth of an icon: James Bond in a tux 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.

Sean Connery in Dr No

Sean Connery displaying cocktail cuffs in “Dr. No”

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.

Timothy Dalton as James bond in a blue suit and Daniel Craig in a tailored suit as James Bond

Timothy Dalton’s baggier late-80s look vs Daniel Craig’s fitted look

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?

Roger Moore in a safari jacket as James Bond

Roger Moore’s unfortunate safari jacket

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.

Pierce Brosnan as James Bond sports a blue blazer and tan khakis for a nautical look

Pierce Brosnan’s appropriately nautical look

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.

A comparison image between Sean Connery and Daniel Craig's classic casual polo look

Sean Connery and Daniel Craig’s classic casual look

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.

Comparison image showing Sean Connery and Timothy Dalton wear interesting suit patterns to fit their surroundings

Connery and Dalton sport context-appropriate suit patterns

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.

Sean Connery as James Bond in Goldfinger wearing a golf outfit

Connery’s Bond in a traditional but elegant golf ensemble

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.

Daniel Craig as James Bond in a light linen suit

Daniel Craig dressed for the tropics in a linen suit

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.

Comparison image showing the evolution of Bond's derby dress shoes from Goldfinger to contemporary

The evolution of Bond’s derbies

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?

Daniel Craig as James Bond in quantum of solace

Craig borrows from Steve McQueen with a 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.

Comparison image showing Sean Connery's Rolex with NATO strap versus Daniel Craig's Omega with NATO strap

Above: Sean Connery’s Rolex with NATO strap; Below: Daniel Craig’s Omega with NATO strap

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.

Sean Connery in the awful Bond outing Diamonds are Forever

Who was dressing Sean for “Diamonds Are Forever?”

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.

Daniel Craig as James Bond in Casino Royale

Daniel Craig’s Bond affects the rakish habit of leaving a shirt button un-done

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.

James Bond jumps without a parachute in Moonraker

Bond’s courage comes not from fearlessness, but calculated risk

“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!

Nick Guzan is a public relations consultant and writer living in Pittsburgh. He blogs about men's style in movies and TV at BAMFStyle.com. His interests include old movies, muscle cars, maritime disasters, fast food, and single malt Scotch.

  • Ryan Lambert

    “It was tied with a Windsor knot. Bond mistrusted anyone who tied his tie with a Windsor knot. It showed too much vanity. It was often the mark of a cad.”
    -Ian Fleming (From Russia With Love, Chapter 25)

    • Stillman Brown

      Ha! Nice

    • Kyle Taylor

      Ironic now, as Craig’s Bond wears the last button of his suit’s surgeon cuffs open. Which is considered quite caddish.

  • Michael Guerrero

    There is a great scene in the Craig Casino Royale where Vesper chuckles at Bond while he is getting dressed in his Tux. Instead of cowering or being embarrassed for taking his appearance seriously he just looks her dead in the face with an expression that says “This is my profession to blend in, my appearance is no laughing matter.” That scene gave me the confidence to start caring and not be ashamed to be the best dressed in the room.

  • Ray

    How has Bond influenced my style? I can’t say I borrow directly from the character but…

    – I own fitted shirts, and a tailored tuxedo
    – At least one stsinless steel dive watch, though Role and Omega aren’t in my price range ( never liked Role anyway ) & also recently was gifted a functional mechanical watch by Marathon with a plain black NATO band, now one of my “go to” time pieces
    – I shy away from the Windsor knot but frequently employ a half-Windsor
    – The knitted Polo shirt and chinos look I borrow frequently, I prefer the lightweight Ascend line from Eddie Bauer but also own a nice linen pair of trou as well
    – I have a navy blazer and know how and when to use one
    – I own Church’s black patent leather formal shoes for the tuxedo, and army-issue black Oxford shoes for other occasions, though the necessities of flying have me reaching for brown leather loafers for ease of passing through security
    – I try to dress to look like my outfit is “effortless” in that it is not an encumbrance, which in turn helps to look confident

  • Kyle Taylor

    I love how the popularity of the NATO strap stemmed from fashion following function. Connery’s Bond wore his Submariner on the vinyl strap because the scene necessitated that he wear the watch over an actual dive suit. Also, http://www.bondsuits.com/ is a great fashion blog that follows all of Bond’s looks from throughout his cinematic history.

  • Chris Fitzsimmons

    Daniel Craig is the reason why I started to care about my appearance. I could not help but admire how sharp he looked and I wanted to look that good.

  • Emily

    Great article!!

  • Zac Silk

    I try to borrow and learn a lot from Bond’s style particularly Craig’s that I am very fond of.

    – I’ve started wearing cardigans, shawl or v neck.
    – I now wear long sleeve polo shirts and chinos.
    – I focus more on fit and tailoring.
    – I try to make my denim well fitted with a break at the shoe.
    – I try to wear desert boots as much as possible.

  • Brian Crawford

    Please reassure me the powder blue, terry cloth romper seen in Goldfinger belongs in the “Mistake” category. The horror.

    • Stillman Brown

      Nice one

  • dustin havinga

    Absolutely the franchise has; witty, respectable, sharp, grit and class.