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What does love look like? Hal Rubenstein has a vision or two. Make that 50. Out this week, his new book, “The Looks of Love: 50 Moments in Fashion That Inspired Romance,” from Harper Collins, is the author’s anthology of various stylistic manifestations of love, sometimes between romantic partners (whether real or fictitious) but mostly between us and various objects of our pop culture affections — celebrities, movies, events.

A self-classified romantic, Rubenstein attributes that persuasion to his childhood. His parents had what sounds like the perfect relationship, one he now views as “an aberration,” in that “emotions were readily available and…expressions of passion and joy were never guarded or edited. “You want to be smart, you want to be thoughtful, you want to be guided by your head,” he continues. “But the reality is your heart has so much more power.”

This story first appeared in the November 4, 2015 issue of WWD. Subscribe Today.

A power that extends to the way we view pop culture, its memorable moments and icons, people who “get under our skin, you get affected by insidious ways.” From Courtney Love and Kurt Cobain to Beyoncé’s “Single Ladies” to Lucille Ball’s reality TV pregnancy, a great deal has gotten under Rubenstein’s skin. Like his earlier “100 Unforgettable Dresses,” also by Harper, “50 Moments” is arranged in no readily apparent order. He wanted to provide a perfect-bound parallel to someone standing in Times Square surrounded by a multitude of images vying for attention, “to feel that you’re getting it from all sides, and that you’re culturally excited.”

There are been-there/remember-it-fondly moments (Woodstock); indelible celebrity moments (the young, bridal-clad Madonna writhing at the MTV Awards; Mick and Bianca Jagger’s wedding) and great fashion shows evaluated through the lens of a fashion professional.

And plenty from movies (“Belle de Jour,” “American Gigolo,” “Love Story”) and TV (“Sex and the City,” “The Sonny and Cher Show,” “Will & Grace”). One big-screen love: “Bonnie and Clyde.” Rubenstein recalls going with college friends to see “Two for the Road” in the days of double-feature, “sneak-peek” screenings. He writes that he came away with no opinion of the main event, “so emotionally shattered and physically shaken was I by [‘Bonnie and Clyde’].”

Yet Rubenstein is an astute social observer. Here and throughout, he elevates what could be charming nostalgic musings into thoughtful analysis on each entrée’s impact on the broader culture. He writes about the trajectory of “Bonnie and Clyde,” at first panned by critics but quickly reconsidered as brilliant. “You want to be like ‘Bonnie and Clyde’ because they’re rebellious just like you were in the late Sixties,” he recalls. “They had that lawlessness that people in the Sixties wanted to have.”

As for the style, costume designer Theadora Van Runkle envisioned the characters as sartorial careerists; he, in dapper suits, she, in jackets, cardigans and midiskirts with a waft of androgyny, both wearing hats for added polish. Yet Rubenstein maintains that film’s huge fashion influence depended upon a bit of cheating — contemporary hair and makeup that made the chic outlaws more relatable to the young Baby Boomer audience that ultimately turned the genre-shattering film into a phenomenon. “And at the core of this incredibly violent film is a love story,” he says. “It’s two young people in love with breaking the law and in love with each other, and figuring out how to love.”

Rubenstein writes about two very different “Thomas Crown” affairs. The first, in 1968, starred Steve McQueen and Faye Dunaway, who insisted on Van Runkle as costume designer. She dresses the two self-absorbed lead characters to highly stylized perfection. “Sometimes love really is surface,” Rubenstein says. “Here are two people who refuse to give in to their feelings. They are the loves of their own lives, absolutely glossy, completely phony lives, empty, useless but driven, and they won’t give it up. It’s covered in layers of magnificent clothing, incredible homes, beautiful watches. They end up apart.”

Rubenstein finds the second “Affair,” with Pierce Brosnan and Rene Russo in 1999, sexier than the original, largely because they’ve been aged-up considerably, “two middle-aged people who have the hots for each other,” he says. “You finally saw two middle-aged people in a hot romance — hot-sweaty-sexy-nude-scene-on-the-staircase romance. This time love does win because frankly, love is more important.” He notes that the body-conscious understatement of Russo’s wardrobe, by Michael Kors for Céline, telegraphs her character’s mature sensuality.

She’s not the only non-ingenue to capture the author’s fancy. A surprising inclusion, 1959’s “Pillow Talk,” stars Rock Hudson and Doris Day as a single, successful career woman that Rubenstein considers a ground-breaking feminist portrayal. “Doris is obviously in her mid-30s, considered old-maid status,” he says. “She’s not only single, she dates some man she’s obviously never going to marry.” In addition to delivering a socially progressive message, the film offers “an incredible exercise in style” that highlights how clothes impact perception, in this case, allowing Day to shed her virginal image via chic clothes that get subtly more sensual as her interest in Hudson’s Brad escalates.

Then there are real relationships, real marriages: the Duke and Duchess of Windsor; Mick and Bianca; Elizabeth Taylor, eight times over. While Rubenstein writes with obvious distaste for the first couple and skepticism toward the second, he buys into La Liz’s romantic ways, 100 percent. (The two got to know each other when he was editor of Malcolm Forbes’ Egg magazine, and she, Forbes’ paramour.) “She was charming and funny and riveting and magnetic and a sorceress,” he says. As for the eight marriages, “Here was a woman so in love with being in love, she couldn’t not be in love. She let her heart lead her. Love ruled. For better for worse, for richer for poorer, for dumber for wiser, love ruled.”

Conversely, he turns a harsh eye on Tom Cruise’s infamous sofa-hopping escapade on “Oprah,” during which the actor  rambled incoherently, flailed his arms and started “assaulting Oprah” before pulling his beloved, the reticent Katie Holmes, into camera range. With that regrettable performance, Rubenstein maintains, Cruise “destroyed his career…[Now] he’s an action hero, not a leading man. You shiver at the thought of seeing him embracing a woman because he creeped us out [on ‘Oprah’].”

If that take seems antithetical to the theme of romance, it’s the moments of skepticism that give the book its bite, in this case, an example of “the inversion of love, the falsehood of trying too hard.”

Not so the relationship of Nancy and Ronald Reagan. Though not otherwise a fan, Rubenstein acknowledges “one indisputable fact: these two people unequivocally loved each other and made no bones about it.” He cites Nancy’s fashion bravado, shunning first-lady propriety and, at 60, wearing a glamorous, arm-baring, crystal-embroidered James Galanos gown to her husband’s first Inaugural, while likening her eyes for her husband to another Inaugural moment, years later. “It’s no different than when Barack Obama looked at Michelle that night and said, ‘How great-looking is my wife?’ It’s the same moment; we just politically may agree with him and not with her. But you can’t deny the power of that emotion between those two people. The emotion trumps everything.”

Then, there’s the love of pure fashion. Rubenstein didn’t choose fashion shows to include; rather, “they own their own locker in my frontal lobe.” Dries Van Noten’s 50th collection was a perfect dinner-cum-show event. Alexander McQueen’s Dance Marathon radiated deep belief in the power of style: “I’m still going to look magnificent even if the world is beating me up.” And two shows by Dior’s John Galliano blew Rubenstein away. In the first, at the Palais Garnier in 1998, the designer “indulged in every fantasy of erotic beauty he could possibly think of.” The next year at Versailles, inspired by “The Matrix,” he went counterintuitive to his surroundings in what Rubenstein calls “the best fashion game of ‘gotcha’ ever watched.”

Advertising also provides rich material: oh-the-smell-of-it Obsession; Ralph Lauren’s first lifestyle-driven advertorial; Baz Luhrmann’s Chanel No.5 film starring Nicole Kidman. Yet an outlier stands out: Maidenform’s “I dreamed…” campaign that lasted 20 years. The ads in the book are a hoot — a camped-out Cleopatra on the Nile, a silver-gloved “knockout” in the boxing ring; a “wanted” Wild West vixen. “It’s an obvious example that nothing exists in a vacuum,” Rubenstein says. “Culturally, everything siphons through the exact same filter into the exact same spout because one has to affect the other.”

As for that “love” connection that made it appropriate fodder for inclusion? This one heralds an emergent self-love in a generation of women awakening to exciting new possibilities. The American family changed during World War II, with women experiencing newfound independence and changed roles. The Maidenform campaign launched in 1949, at first with more or less realistic dreams (save for the lack of a shirt in public), but became increasingly outlandish through the Fifties. “Of course, she’s not going to barge down the Nile, and she’s not going to be in a chariot race,” Rubenstein says. “But she doesn’t feel being called a housewife. It’s demeaning. It’s the idea that a woman is now an integral and equal part of the American household.”

Rubenstein finds it significant that the campaign never features a man ogling the bra-flaunting woman. “As sexually charged as the ads might be in their way, they’re about women being beautiful and saying to other women that you can be who you want to be,” he says. “Of course, you have a guy somewhere. The point is, you don’t need him to barge down the Nile, to discover new worlds, to go into space. That’s the key. If that’s not love, what is?”


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