Audrey Hepburn was the picture of pared-down elegance both on and off screen. Who can forget the belted menswear button-down worn with a long skirt and flat sandals by Princess Ann in Roman Holiday? Or Jo Stockton’s Capri pants and ballet flats in Funny Face (revived years later by Gap for a TV ad). Or, of course, Holly Golightly’s oversize sunglasses and little black dress in Breakfast at Tiffany’s. At a time when curves ruled, Hepburn was the physical antithesis—gamine features, a slender boyish physique and a graceful gait born of years of ballet training. Her style choices were always about comfortable, casual elegance, not sex appeal.
Princess Diana’s evolution from a shy, ruddy-cheeked country bumpkin into a fashion icon happened right before our eyes. When she first appeared on the arm of Prince Charles her outfits embodied youth and innocence: Fair Isle sweaters, Laura Ashley-esque ensembles and ruffled gowns in girly fabrics like chiffon and taffeta. And her wedding dress just may be the best example of her lack of style savvy: an enormous meringue of a gown with a legendarily long train. But as Diana gained confidence, so did her wardrobe. In fact, the moment that signaled her transformation was the outfit she stepped out in the day after Charles’s public announcement of his indiscretions: a sexy, off-the-shoulder black number by Christina Stambolian. From then on, gone were the modest high-collared dresses and Dallas-era power suits, replaced by figure-skimming sheaths and gowns by designers like Valentino, Versace, Ungaro and Chanel.
The Material Girl’s icon status can be chalked up to one very important trait: fearlessness. From the moment she arrived in New York’s Times Square in 1978, Madonna had a pluck and attitude that came through no matter what she was wearing: in those days it was likely torn jeans, a white tee and a treasure trove of jewelry. Over the years her style statements evolved with her music — lacy underwear as outerwear, fingerless gloves, stacks of jelly bracelets and a crucifix for Like a Virgin; black leather jacket and a white tee, plus a platinum crop for True Blue; the famous Gaultier cone bra and sharply-tailored suits for Blonde Ambition; and throwback ’70s disco glam, complete with a Farrah Fawcett coif for Confessions on a Dance Floor. Though her days of dressing purely for shock value (please recall the S&M stylings of the Erotica era) are gone, Madonna still always manages to retain our interest.
Before Jackie, a politician’s wife was never to detract attention away from her husband. And while many eyes were still on Jack, just as many were focused on his perfectly coiffed and outfitted other half. Her legendary ladylike poise was in place far before her Camelot days: she grew up between New York and an East Hampton estate, was an accomplished equestrienne, a society presence and debutante of the year in 1947. Upon her entree into the White House, Jackie hired Hollywood heavyweight, designer Oleg Cassini, to create her wardrobe — though she gave him direction a plenty. The First Lady favored empire-waist gowns, sensible heels, gloves and streamlined suits with knee-length skirts and 3/4 sleeves. Besides Cassini, Jackie also pulled pieces from Dior, Givenchy and Chanel, the designer behind her most iconic look: the pink boucle suit and matching pillbox hat she was wearing when her husband was assassinated. Jackie’s signature style changed drastically when she moved to New York — wide-leg pants, silky blouses, printed Hermes scarves wrapped around her head, white jeans paired with black turtlenecks and ever-present gargantuan shades — but she remained just as inspiring.
The world’s newest style icon represents royalty’s next generation. Since capturing Prince William’s heart, Kate Middleton’s every move has been diligently chronicled by the British press – including where she shops for clothes. And the princess’s sartorial choices have been a pleasant surprise for many Brits: the girl likes a bargain and can often be spotted in the inexpensive boutiques of London’s High Street. For everyday wear Middleton appreciates the easy versatility of a good dress, particularly wrap styles or a floral print by designers like DVF, Joseph, Reiss and Issa (the line’s navy blue dress that she wore to announce her engagement inspired legions of copycats). And, in very un-princess-like fashion, she isn’t afraid to wear something more than once. For more, ahem, regal affairs Middleton turns to designers like Sarah Burton for Alexander McQueen (she designed Kate’s wedding gown) and Jenny Packham for elegant numbers — and, being a true Brit, she always appreciates a stunning topper.
There was no woman more emblematic of ’70s, disco-era fashion than Diana Ross. While she could be considered just as influential during her reign as queen of one of the most successful ’60s girl groups ever (the Supremes, natch, in their matching ensembles), a decade later her fashion sensibility gained an appealingly sultry vibe. Much of it seemingly in step with that of Tracy, the over-the-top stylish fashion designer she played in Mahogany. With her slinky, draped Halston and Bob Mackie gowns, fur stoles, wide-brimmed hats, angel sleeves and sequins galore, Ross always looked ready to shake her groove thing.
Not since the days of Jackie O have a First Lady’s fashion choices so transfixed the public. From the moment her husband hit the campaign trail, people have been closely following Michelle’s version of power dressing. That usually means an equal-parts mix of high and low design — she’s as much a fan of J.Crew and Gap as she is of forward-thinking designers like Junya Watanabe and Alexander McQueen. Michelle both knows what works best on her body and is clearly a longtime lover of fashion: her support of young, and lesser-known designers like Jason Wu, Thakoon and Isabel Toldeo is unwavering and admirable.
She wore the pants. Literally! Neither Hepburn’s physique — tall, slender and boyish — nor her attitude were in line with the bombshell look of the Hollywood age in which she reigned. She didn’t fuss over her hair or makeup (in fact, she wore hardly a trace of it), and dressed with comfort in mind first and foremost. But that doesn’t mean she didn’t ooze glamour at every turn. Besides those aforementioned trousers — wide-legged, high-waisted and precisely-pleated, please — Hepburn’s style signatures included simple, button-down blouses, sharply tailored blazers and polished loafers. Her borrowed-from-the-boys attitude exuded power and confidence and, most importantly, a less obvious brand of sex appeal.
She may be a perennial presence on worst-dressed lists but Diane Keaton has never dressed to please others, and that’s exactly why her style is worth celebrating. She is a non-conformist to the core! Much like Katharine Hepburn, Keaton has always been happy to pay homage to the boys — think houndstooth and tweedy suits paired with men’s button-downs and ties. The shoulders of her oversized blazers inflated with the eighties, and she often paired the jackets with a bowler hats and turtlenecks. When Keaton does go the more feminine route, it’s never in an expected way: full, below-the-knee skirts with wide belts, high-collared shirts, and statement jewelry like outsized brooches or crucifixes. What’s almost always present? A pair of fitted gloves.
The absolute picture of Americana fashion sensibility, Lauren Hutton is as much an icon of style today, at age 68, as she was in her twenties. In fact, her effortless approach to dressing and her laid-back, thrown-together look may be more relevant nowadays than it ever was. She has served as a muse for J.Crew and the Olsen sisters’ fashion line The Row: both featured Hutton in their catalogue and look-book, respectively. Hutton’s personal style has always been a study in undone elegance — slouchy pants and button-downs, loose and easy eveningwear, shirt-dresses, and, the most classic combination of all, jeans and a T-shirt. They key to her look? Not over-thinking it.
Without Bettie Page there would be no Dita Von Teese. No Katy Perry. No Christina Aguilera. The Playboy model turned pin-up queen never wavered from her signature look: teeny tiny bikinis and body-grazing outfits to complement her famously copious curves, reddened lips and that short, blunt fringe known nowadays simply as “Bettie bangs.” In her everyday wear the hemlines were modest (at the knee) and the accessories (like low-heeled T-strap shoes and dainty purses) feminine, but the silhouettes were also always snug, and her petite waist emphasized. Page’s classic cheesecake look is still very much in demand today; in fact there is an entire line (Bettie Page Clothing) dedicated to imitating it.
The original blonde bombshell, Monroe exuded sensuality with every step she took; in fact, it’s rumored that the stilettos she wore always had one heel shaved down to achieve that slightly off-kilter gait, so she literally wiggled while she walked. During her brief life, Monroe sported what are now considered some of the most iconic outfits of all time: the billowing white halter-neck dress worn over a subway grate in The Seven Year Itch, the pink satin strapless number with opera-length gloves and layers of sparkling jewels in Diamonds are a Girl’s Best Friend, and the sheer, skin-colored, rhinestone-encrusted dress she had to be sewn into to sing “Happy Birthday” to JFK. In her life off-screen Monroe appreciated a good skintight wiggle dress paired with heels and little else in the way of accessories (she sang about diamonds, but didn’t really wear them), as much as she did more casual ensembles, like Audrey-esque sweaters and capris or jeans. But with those languid, bedroom eyes, tousled blonde crop and slightly-parted lips, Monroe managed to make everything she wore look sexy.
The definitive Hitchcock blonde turned fairytale princess, Grace Kelly had a natural, quiet elegance that shone through both on and off screen. Whether she was wearing a gown and tiara, or capris and a button-down, the key to Kelly’s look was always appearing understated. She had a fresh-faced innocence about her that won plenty of approval in the ’50s, and an innate style sensibility — Kelly was drawn to unfussy designs by couturiers like Balenciaga, Yves Saint Laurent, Dior and Givenchy, or alternatively, classic preppy fare like khakis, which she often paired with crisp button-downs and a printed silk scarf. Kelly had many defining fashion moments, but the one that is referenced most often was pure happenstance. A year after marrying Prince Rainier III of Monaco in 1955, she used a boxy crocodile bag by Hermes to conceal her growing baby bump. Thanks to her international style icon status, the bag quickly became famous and so Hermes renamed it in her honor; thus was born the Kelly bag, which to this day has legions of people willing to shell out up to $25K to own one.
Debbie Harry’s distinct sound pulled influence from both the disco-era past and punk-rock future; and so did her look. It was equal parts ‘70s glam — slinky, one-shouldered dresses perfect for dance floor twirling and, as she proved, thrashing about on stage, heels and hot pants — and hard-edged rock: think skin-tight, high-waisted black jeans, leather jackets, ripped-up tights and all manner of beat-up rocker tees. The one constant that remains even to this day? That signature shaggy bleached blonde crop.
Marilyn may have been the original blonde bombshell, but Brigitte Bardot was nipping at her heels from across the pond. The French’s resident kittenish blonde first emerged wearing typical ‘50s fare — girly, wasp-waisted, full-skirted dresses — before settling into her own style routine. Her wardrobe for summers spent in St. Tropez consisted of countless bikinis (she is credited with popularizing them), short shorts and easy sundresses, but besides that her regular ensembles were usually a casual affair. Bardot favored sweaters (often with a wide, off-the-shoulder silhouette now referred to as the Bardot neckline) and tees paired with cropped jeans and a rotating collection of ballet flats; this bombshell liked to be comfortable. And Bardot is just as famous for her beauty look which was va-va-voom personified: black, winged-out liner for her sleepy, bedroom eyes, pouty pink lips and that signature tousled and curledchoucroute hairstyle.