Can Woody Allen Do An ‘Annie Hall’ for Men’s Fashion?

In his new movie, the veteran director exalts the fashions that ruled in the '30s, when glamour and comfort went hand in glove.

Who can forget Daisy Buchanan's reaction when Jay Gatsby tossed a myriad of pale crisp oxford shirts toward her in The Great Gatsby? "It makes me sad," she sniffed—"because I've never seen such beautiful shirts before!" At that moment, a historical love affair was born: that of status-seeking men and luxe tailored haberdashery that reeks of position, class, and, oh yeah, money.

Woody Allen, the modern F. Scott Fitzgerald documenting American class struggles of the middle scratching its way upwards—and of unrequited love—has often displayed these conflicts in wardrobe. Which is why many of his films have become unexpected fashion influencers: Annie Hall with its Ralph Lauren menswear, Manhattan, Hannah and Her Sisters, Match Point, and, of course, Midnight in Paris, set in the '20s. But none of those films can match the wardrobe in excelsis of Café Society, set in the glam golden early '30s circles of Hollywood and New York.

Jesse Eisenberg, wearing tweed trousers and sweaters as Bronx-born Bobby Dorfman, arrives in Hollywood to hit up his superagent uncle Phil Stern (Steve Carrell) for a show biz jumpstart. As he moves up to script reader, Bobby moves into earth-toned suits with stiff shirts, sweater vests, and ties, and then to slick white dinner jackets, bow ties, and tails, when he returns to New York as the host of a zebra-boothed club called Les Tropiques. Bobby's older brother Ben (Corey Stoll) is a full-on gangster in extra broad V-shaped long-torso suits and fedoras. Carrell dons pale ice cream suits with wide shoulders and high-waisted baggy pants (called "oxford bags" when they came into vogue in 1925), evening tails, and chalk-striped suits with printed shirts and ties. Kristen Stewart as Phil's secretary goes from short-sleeved rayon chemises, flared trumpet or tennis skirts and T-strap shoes to Rita Hayworth siren gowns (some by Chanel). And Blake Lively, as a society girl who ma rries Eisenberg, swans in lame bias-cut halter gowns—all the women are draped in Chanel fine jewelry from the Chanel archives. Each of these looks was inspired by the then-new class of silver screen Hollywood stars—the first time stars became the major fashion influencers of their time.

Café Society costume designer Suzy Benzinger (a veteran of Allen productions as well as Broadway musicals) acknowledges that it's getting harder to source period clothes these days, since the proliferation of period projects has been scarfing it all up.

"All the best wardrobe collections of period clothes are in Europe," says Benzinger. "So we did a lot of sourcing in Italy. Jesse Eisenberg's first suit was from Pirelli Design in Rome. The rest were all made by Marty Greenfield, the oldest tailor in the world, survivor of the Holocaust. He owns the largest tailoring shop on the east coast, in Brooklyn. He's made all of Obama's suits, Mayor Bloomberg. I had Jesse come to his shop in Brooklyn. Marty knows the '30s—he made all the stuff and told us wonderful stories along the way. And Woody has very strong opinions with fashion—surprise!"

Yes, Allen's aware of the appeal of these clothes, both then and now, as American perennials: the dawn of modern fashion post-Victorian structure.

"If you look at Ralph Lauren's newest collection" says Benzinger, "it's totally '30s. Ralph respects the art of tailoring—and now you can't find these kinds of tailors. It's sad. We did use some of Ralph's shirts and pants in Café Society. In the double R line he has a lot of stuff, year after year, that's totally '30s. Ralph cuts proper shirts like '30s—he has 1930's collars on these shirts, we used those right off the rack. We used Ralph's shoes like crazy, and his neckties and bowties. And his men's sweaters—he recreates knitting from '20s and '30s. It was so rewarding outfitting the male actors. They came in T-shirts and sweatpants, and left saying, 'These period clothes make me feel so grown up and sophisticated.' When they all got into costume, everyone in the crew would look at the cast and sigh,  'Why doesn't anybody dress like that anymore?'"

Indeed, why? Well, some do and some have never stopped. Ralph Lauren is still sending out these kinds of classics, as are Tommy Hilfiger, Neil Barrett, and Thom Browne.

Bruce Pask, men's fashion director at Bergdorf's, notes, "The tailored clothing men wore on film then, with strong, structured shoulders, wider lapels and neckties, and high-waisted trousers, cut a rather heroic profile that was certainly emulated. I think Ralph Lauren is a designer who beautifully references and translates that Old Hollywood aesthetic, often incorporating those classic menswear elements like pinstripes, vested suits and silhouettes that emphasize the body. The Spring '17 menswear collection he just presented in Milan featured fuller, double-pleated pants, trim deco graphic sweaters, double-breasted suits, and shawl collared evening jackets that could have jumped right off the silver screen yet were tailored for the modern man."

"You can also see broader, stronger shoulders and boxier shapes in the Balenciaga spring 2017 men's show," says Tod Hallman, a Hollywood stylist, blogger, and menswear influencer. "Guys are tired of all these super tight clothes—as much as they might workout. It's getting boring."

Bronwyn Cosgrave, a fashion historian and the curator of the traveling exhibition "Designing 007: Bond Style," observes, "That '30s men's silhouette is relaxed—not the Mad Men late '50s, early '60s button up restricted look. The '30s was the kind of look where you take off the jacket; men love taking off their jackets. They like looser trousers that move more easily. It's the antithesis of the Hedi Slimane skinny look. I think we're moving into a moment of more relaxed luxury. And that soft suit look is a classic—Armani brought it back in the '70s. A writer can wear it, and a banker can wear it. It's very Saville Row."

Hollywood men's stylist Dave Thomas, who dresses John Legend, Lionel Richie, Harry Connick Jr., Calvin Harris, and Boy George, admits he's starting to see some movement towards a looser silhouette. "That sexy tight single-breasted look by Slimane has been happening so long—now even Zara and Ryan Seacrest are doing it. It's time for a change. You can see it with the return of the loose duster coat, and in color starting to sneak in men's clothes.

Simon Collins, former dean of Parsons and a fashion expert/consultant, claims, "The 1930s menswear silhouette always comes back because that looser cut tailoring is just comfortable—and when it's done well, it can look very manly and powerful. See Armani, circa 1982. And who doesn't want to look like Jay Gatsby—Redford, not DiCaprio? Overall, the menswear silhouette has begun loosening up over the past few seasons. It's a slow shift, but many brands are moving away from that very skinny, strictly tailored suit that was the look for many years. Even J. Crew, which brought the skinny suit to the masses with its Ludlow suit last year, introduced a more relaxed version called the Crosby. But you can also find that look at Bottega Veneta, Berluti, Zegna, and Ralph Lauren, just to name a few." 

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