Digging through the archives of fashion history is like sitting down for dinner with your aging relatives to grill them on what life like was back in the olden days. While you don’t need to have a front-to-cover handle on how Great Grandma Hearst rationed herself through the depression, you’ll benefit from soaking up some of the details—like how she used to make dresses out of 100-pound flour bags and darn socks by the light of candles she made herself. Why know all this stuff? Because history often repeats itself. And in fashion, history repeats itself all the time.
Right now, the ’90s are on playback in a dozen different ways—some good (chokers), some not so good (belly button rings). The throwback piece I’m more readily capable of embracing into my modern wardrobe is the slip dress, which feels so positively of-the-moment it’s hard to understand why it’s been gone for so long. But fashion, as we well know, oscillates somewhere between ADD and amnesia, burning through trends like wildfire and leaving them to go fallow for decades before implementing a proper reboot.
Like flannel button-downs were to Seattle grunge bands, the slip dress became the feminine answer to an era that stripped down the shoulder-padded artifice of the previous decade. If Nirvana was the answer to the inconsequential theatrics of 1980s glam rock, the slip dress was the quiet, restrained response to sequined prom gowns and metallic taffeta. The look was deceivingly simple, letting a woman’s personality speak for itself without needing a garment to do it for her.
Today, designers are offering their take on the sleek silhouette, borrowing from the old and injecting it with the new. During the spring 2016 shows, the slip dress influenced Burberry’s “Helen of Troy at a rave circa 1996” look, as did it Saint Laurent’s “Carrie goes to prom again” number in silver lamé. It came in satin, leather, lace. Hems were high and low. Straps thick and thin.
Whatever the updates, the ethos of the slip dress remains the same: easiness of wear. It’s the kind of piece that you just throw on with whatever you have and head out the door, and when you get compliments at the party you shrug and say, “What, this old thing?” before knocking back the whole champagne bottle and chain-smoking your 17th cigarette. At least if you’re Kate Moss, who kicks off our list of the five slips that changed fashion history, each paving the way for today’s trend.
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If there’s a slip dress ambassador on this planet, it’s Kate Moss. From mags to street style, there are dozens of Moss slip dress moments, which makes picking a particular favorite exceedingly difficult. For sheer (pun intended, apologies in advance) shock value, we’re going with the 1993 see-through slip she wore to Elite’s Look of the Year party back in 1993. Knickers on, nipples exposed, Kate already knew how to make an entrance. Honorable mention goes to a less transparent turn in a shoot with Patrick Demarchelier for the July 1993 issue of Harper’s Bazaar.
Remember when Gwen and Brad dated? That was blond. In 1996, before the couple had matching haircuts, a not-yet-super-famous Gwyneth hit the Oscars red carpet in a beaded Calvin Klein slip, all matte lipstick and hip bones, as she accompanied a very young Brad sporting super-aggressive lapels. Pitt was there for his Best Supporting Actor nomination for 12 Monkeys. Two years later, Gwen returned to the Oscars on her own terms, wearing the pink gown to end all pink gowns, which I only wish counted as a slip dress otherwise it would have made this list. That year, she scored Best Actress in a Leading Role for her work in Shakespeare in Love.
Winona Ryder was the physical embodiment of ’90s fashion. On her own time, she held it down in the casual/masculine department with baggy jeans, leather jackets, and oversize suits. On the red carpet, Winona was the queen of a kind of gothic elegance that arguably paved the way for the likes of Rooney Mara. In 1993, she showed up with Dave Pirner of Soul Asylum (a very ’90s boyfriend, BTW) in a purple velvet slip dress that had a harder, darker edge than many of the others on our list. Wino forever… swoon.
There are few wedding dresses as frequently referenced as the one Carolyn Bessette wore in her wedding to the unofficial Prince of America, the late John F. Kennedy Jr. A former public relations exec at Calvin Klein, Carolyn was well-versed in the art of less is more, and for her wedding—an envy-inducing Southern affair—she went with a bias-cut silk slip designed by Narciso Rodriguez. The rest, as they say, is Pinterest history.
Don’t know how to pull off a slip dress? Read more about how to channel your inner ’90s babe here.