The films share far more in common than just their wafer thin plot. The most relevant similarity, for our purposes, is that both films were costume designed by women with close ties to the fashion world. When Theadora Van Runkle designed the 1969 version, she had already made quite a name for herself designing another film that is still looked at as a paragon of sartorial excellence, Bonnie and Clyde. The classic film about the starcrossed bank robbing lovers had not only been a hit, it had inspired international style trends. Women started wearing lower hemlines and berets after the leading lady (also Faye Dunaway), while double-breasted suits with wide lapels favored by Warren Beatty in the film, came back into fashion for men.

Suddenly, Van Runkle found herself in demand as both a costume designer and stylist. She handled a number of celebrity award show dresses during that period, including everything Dunaway wore. She single-handedly brought sensibilities from the 1930s back into fashion, and she became so well known that she is even name checked on screen in cult (albeit goofty) comedy Troop Beverly Hills (1989).

Van Runkle was a natural choice to design The Thomas Crown Affair. Not only did she launch a defining trend in ‘60s menswear, but she also helped to shape the style (excessive in its luxuriousness; simple in its timeless slim cuts and classic casual nature) that would make Steve McQueen a fashion icon. The relationship continued to blossom with McQueen as she designed wardrobe for McQueen in The Reivers and is responsible for some of his best known film looks in Bullit.

Van Runkle was enough of a style maven to know her strengths and weaknesses, however, and she handed off her suit responsibilities. Several consultants and tailors specializing in menswear were brought in to work on the film, including Ron Postal and Alan Levine, but it was ultimately legendary tailor Douglas Hayward who would be responsible for the suits.

Unlike Van Runkle, the 1999 remake of The Thomas Crown Affair was designer Kate Harrington’s first foray into costume design. Like Van Runkle, however, she had a history of experience in the fashion world. First, a model, then a magazine fashion stylist, and then a stylist on feature films, Harrington’s career before Thomas Crown suited her perfectly for creating a wardrobe steeped in haute couture. It’s no coincidence that Van Runkle and Harrington had made a living in offscreen fashion before taking on their respective films; when you want to create a look people admire, it helps to know what they like to wear in the real world.

“I went shopping.” Harrington told the LA Times about her approach to the film at the time. By this, she meant that this project wouldn’t be about sketches or patterns: It would be about buying clothes that would lend the film an air of sensual elegance. Like Van Runkle, this meant that she would turn to a veteran tailor for her suits. She bypassed giants of the day like Prada and Gucci and went with lesser known but no less respected designer, Gianni Campagna.

Campagna was actually an inspired choice, even if he wasn’t a household name. The designer was Milan’s premiere bespoke tailor at the time and had plenty of Hollywood clients, as well as customers with the kind of wealth held by the fictional Thomas Crown. He counted the CEOs and founders of companies like Revlon and Mattel among his clientele. At the time, Sharon Stone remarked that Campagna was, “an old-world artisan of at the finest level.”

The classic feel of Campagna’s suits is no accident: He himself was a bit of a classic. Quite old by the time that Harrington came calling for Thomas Crown, Campagna brought a long history of Hollywood experience to the film. He had worked on suits for Clark Gable and Gary Cooper in the 1950s and ’60s, and wanted to bring that same elegant, classy tradition of the first Thomas Crown to the updated film.

McQueen’s Suits

McQueen’s look in the 1969 Thomas Crown Affair is anchored by classic, perfectly tailored three-piece suits. The ’50s saw a broadening of the men’s suit frame, a trend that would reach its almost parodic pinnacle in the ’80s. However, in the ’60s, mod culture had pushed back against this trend. The Mod movement reacted against the boxy look of Madison Avenue, throwing back to a slimmer form. Van Runkle and Hayward pushed a slimmer profile for Thomas Crown, which has proved to be the more enduring trend in subsequent years.

The suits in the film are not just slimmer than your typical business attire, they are also more colorful. Perhaps the most iconic suit in the film is the first one we see. McQueen is attired in grey Prince of Wales plaid and a light blue shirt. The mother-of-pearl cufflinks and royal blue silk tie accentuate the already bold choice. Playful blues, greys, and browns recur in McQueen’s formal wear throughout the film. The colors never draw too much attention, but they certainly stand out.

Though Hayward was a Saville Row tailor who often catered to Hollywood stars, his work offered an earthier sensibility that suited McQueen. Commentators are quick to note that Hayward styled himself a “working class lad” and it was a point of pride for him that his work be viewed as egalitarian. In that era, Hollywood male movie stars had to walk a fine line between classy dress and manly swagger and it is no coincidence that McQueen, as well as fellow stars like Robert Mitchum and James Coburn, gravitated towards Hayward’s looks.

McQueen’s casual wear in the film is equally bold and stylish. He wears the kind of suede desert boots that would forever be associated with the star, accompanying them with slim khakis, tight, patterned sweaters and slimming windbreakers that all worked together to create a casual, classy and timeless look.

Brosnan’s Suits

Campagna suits were the top of the line at the turn of this century. The average cost was about $3,500, and they were known for their lightweight Super 150s wool. Just as Hayward favored a slimmer silhouette than had been popular in the 1950s, Campagna suits offered a slimming contrast to the large frame suits that had dominated the 1980s. For better or worse, history repeats itself, especially in fashion.

Matt Spaiser offers detailed analysis of James Bond’s (and the actors who played him’s) various suits at The Suits of James Bond, and because Brosnan took on Thomas Crown in the middle of his time as Bond (Brosnan’s first turn as Bond came via 1995’s Goldeneye), he offers similarly detailed analyses of the suits in this film. He describes the one of the early suits Brosnan wears in the film as, “cut with a clean chest and straight shoulders with roped sleeve heads. The jacket has double vents, straight pockets and flaps with four buttons on the cuffs...The suit trousers are belted and have double reverse pleats and tapered legs.” Though double vents have since fallen out of fashion, the slimmed silhouette still holds up today.

These hints of the classic extend beyond broader tailoring choices and into the details of his suits. One suit has a herringbone weave. Some featured peaked lapels. Pocket squares make several appearances. The jackets tend to have classic proportions. Spaiser notes that Brosnan’s suits in Thomas Crown are even more old-fashioned than what he wore as Bond. While Brosnan’s Bond was meant to be an update, his Thomas Crown was intended as a throwback.

While there were certain ’90s flourishes—for example, Brosnan often wears ties close in color with his shirts, as any Regis Philbin-era Who Wants to Be A Millionaire? fan will remember was the fashion then—the core look remains classic, and thus, timeless. There are also dated flourishes in the 1969 version, as is evidenced from the mock turtlenecks. But, in both cases, these flourishes are countered consistently with the classic. It is no accident that both version of Thomas Crown favor a three-piece suit. The looks in the 1999 reboot haven’t aged quite as well as the costumes from the original largely because Harrington didn’t put quite as much care into cultivating a classic look in Brosnan’s more casual scenes. Brosnan’s baggy golf wear, for example, looks painfully dated (or at the very least boring, when compared to the je ne sais quoi seen in McQueen’s on-screen golf gear) today.

Additionally, Harrington was hampered by a strange clause in Pierce Brosnan’s contract. As mentioned, Brosnan was playing James Bond at the time. While is version of Thomas Crown was going to require his character to attend a black tie event, his Bond contract stated that he couldn’t wear a tuxedo with black tie outside of his film appearances in long-running franchise. As a clever workaround, Bronson donned a midnight blue tux, left the top two button of his Turnbull & Asser shirt unbuttoned and draped a white bow tie around his neck instead of tying it. While the film avoided clashing with Brosnan’s contractual obligations, the juxtaposition (both against the other characters in that particular scene, along with his other suits throughout the film) is sometimes remembered as “the ugliest suit” in cinema history.

A Look that Endures

Though they were seperated by decades and sometimes were rather far apart in terms of taste (Van Runkle’s design was more playful; Harrington’s more new-millenium sleek), both film versions of The Thomas Crown Affair offer a recipe for creating a timeless formal costume design.

Rather than falling head over heels for the trends of the moment, both designers asked their preferred tailors to look to the classics. McQueen’s vests and Brosnan’s herringbone might seem like minor touches, but if you consistently add a pocket square here, and a peaked lapel there, the result is a classic air that permeates the entire wardrobe. When trends of the moment were included, they weren’t to be overdone. Yes, McQueen’s look is colorful, but it isn’t Austin Powers. While Campagna suits allowed for touches of ’90s fads, no one would mistake Brosnan’s look for turn of the century Regis Philbin.

The reality is that we don’t know what stands the test of time until the history books are written. If you are trying to create a timeless look, you have to use timeless ideas as inspiration. You also have to tamp down the worst excesses of the current moment, even if a particular trend is all the rage.

“Classic” is a loaded word. It doesn’t simply mean old. A better synonym is “enduring.” Because the designers and tailors behind these looks sought inspiration from the enduring, the looks they created are likely to live on.

While the actual filmmaking behind either rendition of The Thomas Crown Affair isn’t likely to get the Criterion treatment, it’s safe to assume that the wardrobe from both films will continue to appear on those “Best Film Style” lists for years to come.