Breaking down 12 of James Bond’s biggest fashion statements

In retrospect, James Bond’s , plays like a stripped-down affair when compared to the blockbusters that would follow. But while many of the series’ signatures would be introduced in Sean Connery’s ensuing films, 007 came right out of the gate with a definitive sense of style.Credit where credit is due to Ian Fleming for creating the character, but—as Crowley notes—so much of the visual language of Bond was defined by Dr. No and its director Terence Young, who brought Connery to tailor Anthony Sinclair for his fitting. The spy first introduces himself to Sylvia Trench—and audiences around the world—while wearing a midnight blue shawl-collar tux. Even from across the baccarat table, it’s an unforgettable look that announced Bond as a man who took his wardrobe as seriously as the mission at hand.Here, Crowley dissects the details that make this tux such a timeless fit for 007:On the surface, it’s a very, very classic—very English—Conduit Cut, as they call it, which has roots in a British military silhouette. Obviously, there aren’t any of the ornamental trimmings, there’s no epaulets, or that sort of detail. It’s more about the actual cut and shape of his coat and the trousers, which are slim and straight with the tapering towards the bottom. [The coat] is nipped in at the waist, and then there’s the fullness in the chest—which is referred to as drape—so you get that slightly bigger chest and slightly smaller waist. And that, combined with a relatively natural shoulder, is just a very flattering look. It’s elegant, and it’s timeless.

Perhaps just as iconic as the midnight blue tuxedo is the white dinner jacket Connery’s 007 sports in Goldfinger’s action-packed cold open—made all the more memorable by the fact that it’s revealed, wrinkle-free, from underneath Bond’s wetsuit. While Crowley notes that keeping the jacket perfectly pressed is achievable, he wonders how Bond managed to not crush that red carnation he seemingly pulls out of nowhere.Lingering questions aside, Crowley weighs in on why the look is the perfect statement piece for 007:The white dinner jacket is certainly bang-on for the time period, though it had been a fixture for specific occasions from the 1920s onward. Varying silhouettes have been in fashion throughout the decades—certain periods favored more of a shawl collar, or a peak lapel—but it feels like a staple. The white dinner jacket is considered more of a warm weather play, and it’s decidedly less formal, so that that adds a certain element of Bond-ness to it. I mean, he’s an officer and a gentleman, right? There’s kind of this idea that, even if he’s not in [a traditionally] military uniform, he’s still in a kind of uniform.Our expert also singles out some of the subtle touches that make the look feel especially elegant. For example, Bond’s otherwise classic, white pleated evening shirt has a beautiful satin stripe running through it—a chic touch that “definitely has the ‘60s flavor.” As he points out, menswear is all about the details:Historically, womenswear is about a silhouette, it’s about big, bold statements— it’s about the shape of a skirt, or the placement of a waistline, etc. Whereas menswear is more detail-oriented. Even though the silhouette of men’s clothing has changed considerably over time, it happens more slowly. So, generally you end up more with these slightly quieter, subtler touches instead of big seismic shifts in trends. I mean, ultimately, what Bond’s wearing here—with minor tweaks—could be from 30 years earlier.

Even James Bond takes some time off. Early on in Goldfinger, the spy’s seen vacationing at a Miami resort when duty calls yet again: His CIA ally Felix Leiter shows up and asks him to keep tabs on another hotel guest, Auric Goldfinger, whose shady dealings have made him a hot target. For modesty’s sake, 007 slips on a baby-blue onesie over his swim trunks and gets to work.Is it the most functional spywear? Not necessarily. But is it fashionable? Well, that’s up for debate. Our menswear expert shares his thoughts:I think this one is so famous for its silliness, in a way. But it’s that thing where, if you’re handsome and you have the right build, you can kind of pull off anything. And certainly, in the film, Connery makes it look very natural. Or, as natural as possible. But I love terrycloth. Or, as the English call it, toweling. Terrycloth is great loungewear, or cabana-wear. It was very big in the ’60s, and somewhat in the ’50s, but this definitely speaks to the style of the Goldfinger era. You’ll see all kinds of variations on terrycloth, though I’ve never seen this kind of one-piece situation in person.

In his only go at the role, George Lazenby had the unenviable position of trying prove to audiences that there could be more than one 007. While he never quite gelled, the former model brought his own sense of style to , depicting a more fashion-forward James Bond. In this striking look, the spy’s about ready to hit the greens for some golf when he’s kidnapped by members of a crime syndicate. The orange mock turtleneck knit top paired with a brown jacket and matching trousers is a far cry from the more Connery’s Bond wore in Goldfinger just a few years prior.While Crowley applauds the bolder wardrobe, he notes that Lazenby’s looks lack the true timelessness of the Bonds before and after him:It’s a clear example of one of the two kinds of Bonds, right? There’s your classic English, elegant, sartorial Bond. And then there’s fashion Bond—cool Bond. And I think this is definitely one of those those instances where they were trying hard to make trying to make him cool. This look is so of its time, so it does feel dated, although, perhaps if you changed his hair, it wouldn’t be completely out of place today. Trends come and go in cycles.

When Roger Moore took over the 007 mantle, the series embraced his winking approach to the role, but also leaned into its sense of adventure, making the spy a proper globe-trotter. Because of that, Moore’s Bond feels more focused on a tactical, action-ready wardrobe than it does formalwear—ready to rumble in the jungle or wherever the mission may take him.One standout is the sleek, all-black get-up he dons for Live And Let Die’s final act, which calls to mind Steve McQueen in with his over-the-shoulder gun holster on full display (and, for what it’s worth, both looks seem to be an influence on ’s go-to spycraft threads). Crowley notes that this is definitely Moore’s Bond at his most practical—though the outfit is not without its sartorial pleasures:I love this look—it’s simple and timeless. The [flared trousers] have a tightness to them, which definitely speaks to the early ’70s, as does the turtleneck, which has long been a cornerstone of menswear. But you could definitely argue that the turtleneck’s heyday was from the late ’60s through the ’80s, so it’s not surprising to see Moore in one here.Crowley says one of his favorite signatures of the 007 series is that, no matter where duty calls him, Bond has the perfect outfit for it:I love this idea of Bond as a citizen of the world—he’s ready for anything! You can plop him down anywhere, at any time, and he’ll magically have the right fit He’ll have exactly what’s needed, whether he’s in the Alps, or in London, or in Rio, or in Mongolia—he’s just going to have the right stuff. And that’s, I think, the magic of Bond: He’s always prepared, and it’s so seamless. You never hear him wonder, “Now, what am I going to pack for this trip!”

Another common thread throughout Roger Moore’s tenure is the leisure suit, seen here when Bond arrives in Macau in . A more casual approach to the suit featuring a shirt-like jacket, the leisure suit was initially popularized in the United States, but was itself inspired by European hunting jackets. As our menswear expert notes, this structured outer layer is commonly referred to as a bush jacket, or safari jacket. The outfit feels both of the era, and a nod to Bond’s history as an agent of the British Empire:There are a lot of fashion trends that were revived in the ’70s but with a distinctly ’70s twist. For instance, on the surface, this is a very classic kind of military look. It’s what’s called a bush jacket, like what you’d see someone wear on safari. These have long had a quasi-military utility to them—a jacket with epaulets, usually with patch or flap pockets. And while, ostensibly, this could be perfectly at home anywhere in the 20th century, the bush jacket had a huge moment in the ’70s. It’s long been worn by people while hunting, but this era made it cool; the ’70s turned it into something smart and chic, and you’d often see it in a dressier context.But there are a lot of finer details that catch my eye. Bond’s wearing the jacket with this fantastic shirt, which is probably a Turnbull & Asser shirt because it has that turned-back cuff—a signature of theirs. It’s kind of like a French cuff with buttons. It doesn’t have cufflinks, but it has a double cuff, which is a very cool, very English look that just fits right into everything about Bond.

After Moore’s campier take on Bond, the franchise pivoted hard in an attempt to meet the times, bringing in for a 007 with an edge. Dalton’s was a no-nonsense spy who would frequently forego the full tuxedo for something more casual, like a blue button-down and a windbreaker.One notable exception came in the opening of License To Kill, in which Bond is a groomsman for his American pal Felix Leiter. En route to the wedding, the two are called into duty and, next thing they know, they’re chasing down drug dealers in morning dress. It’s somewhat incongruous to catch Dalton’s simpler, brutalist Bond in something so formal, but Crowley notes this more traditional wedding look was on-trend for the time:He’s wearing what is—in the U.K., to this day—actually still relatively common for daytime formal. This is still something that you can rent pretty regularly in the U.K. It’s also, basically, what you would wear to Royal Ascot [horse races]—the gray morning suit with the cutaway coat and everything. The only thing about this that makes it wedding-specific is that the tie is an ascot. But it’s funny because—even though it’s timeless, like it could be from anywhere from 1870 to today—it somehow has a little late-’80s flavor to it.Bond’s wedding attire comes complete with a matching grey top hat, which takes a bullet in the opening action, but is only ever seen on his head for a split second. Crowley cites its absence as a fascinating detail because, by this period of time, the hat’s popularity had been in sharp decline. And in fact, 007 hasn’t regularly worn a hat since Connery’s earliest films. As our expert notes, “[From the ’60s onward], you’re really seeing hats less and less and less. So it’s actually quite striking to consider that James Bond—even though he is the quintessential English gentleman—has left hats in the past, too.”

With the Cold War in the past, that placed the hero squarely in the ’90s—regrettably, he also brought a lot of era-appropriate, ho-hum outfits along with him.But there were a few standout fashion moments from Brosnan’s run, not least of which was the brown, calf-length, double-breasted coat (complete with a matching tie) 007 wears during his briefing with Q shortly after arriving in Hamburg in . It’s a different silhouette than we’re used to seeing on Bond, and Crowley remarks it feels so out-of-the-ordinary because it’s largely obscuring the spy’s signature uniform: The suit.It’s striking because the coat feels it’s a little bit surprising. Not the coat itself, which is very traditional, but the fact that he’s wearing one to begin with. To me, a coat is something practical. It’s something that you you wear because you’re going to be outside, you’re going to be cold, right? I mean, considering the longer cut of this cashmere, it’s not meant to be purely practical. So it’s not essential to the sense of survival, but here it serves as an essential part of the English gentleman. It’s the proper thing—the “done thing,” as the Brits say.

For Brosnan’s final film in the series, , Bond rocks one of the most surprising looks of all: A billowy Hawaiian shirt—one might even call it “Tommy Bahama chic.” The floral pattern is a rarity for 007, but perhaps even more unusual is just how baggy and loose it looks on the spy who’s so frequently tailored to a t.To cut Bond some slack, he did just land in Havana where the rolled-up sleeves are certainly appropriate for the warmer weather. But our menswear expert agrees that this is one of his lesser looks:Yeah, this one’s so bad. I’m not anti-’90s, or anti-[Y2K-era fashion]—there’s a lot of great ’90s trends that I love—but this is one of those things that’s just blah. I know that he’s on vacation, but he’s just wearing dress pants with the most boring Hawaiian shirt. It’s just kind of joyless. I think you could do this kind of look—like, a Bond from an earlier era could wear a floral print and probably have it look pretty cool. But this late-’90s styling just doesn’t hold up. Thinking back on some of what we’ve talked about, like the George Lazenby turtleneck, or the the Sean Connery terrycloth romper: Are they the best Bond looks ever? No. But they’re making a statement in their own way. Whereas this is making no statement.

Now this, on the other hand, is some warm-weather 007 fashion done right. A few years after Brosnan, the franchise introduced Daniel Craig as a gritty Bond for the era of and . With piercing blue eyes, blond hair, and a muscular build, Craig immediately stands out among his predecessors on a purely physical level, which gave the series’ creative team an opportunity to revamp the spy’s style once again for .Still, one of Craig’s defining fashion moments as 007 is one where he’s not wearing much of anything at all. Emerging from the ocean in tight, light blue La Perla swim trunks, Craig strikes an instantly iconic image that harkens back to the introduction of Ursula Andress’ Honey Ryder in Dr. No—the original “Bond Girl”—and, to some extent, Halle Berry’s Jinx in Die Another Day.As Crowley notes, the suit’s retro look—the color, the low rise, the inseam—also feels like a nod to the original Bond, Sean Connery:This cut was not necessarily on trend with American fashion at the time, but it feels very European and very nostalgic. It’s not dissimilar to what Connery wears in some of the earliest Bond movies. So it’s a great fit, but it’s also winking at the series’ history, referencing the Bond of another time.

Craig’s bulldozer of a Bond always seems ready to jump into the action at a moment’s notice. In ’s opening action set-piece, 007’s rendezvous quickly leads to a hot pursuit, and suddenly his grey Tom Ford suit becomes his battle armor.Of course, this pick-and-pick look—a woven effect using different color fabric— isn’t the most practical for a high-speed chase, but it’s lightweight and flexible enough that Bond can pull off some gasp-inducing stunts while still looking the part of a proper English gent (there’s even a split-second where he takes a moment to adjust his cuffs after a daring leap onto a moving train). Though Craig’s Bond always does the job in style, our menswear expert admits he’s never been the biggest fan of his fashion sense:I definitely don’t dislike Daniel Craig as James Bond, but I don’t really love his style because I think it looks very ordinary, it looks very Suitsupply. It almost looks like he could work at a bank! Of course, that really is the prevailing look of this era, so it makes sense. Bond has always been timely, he’s always been of the moment, he’s always been on trend, so, in that regard, this is absolutely right. However, it just it feels like it always feels like he’s about to burst out of the suit. It’s kind of surprising that this was tailored by Tom Ford because, historically, a Tom Ford is more drape-y and sexy in a way that feels right for Bond—it feels more luxe. Typically, there’s a nice cinched waist, a very strong shoulder, and a well-cut sleeve that’s not too too skinny; they’re just great-looking suits.