Couple dressing is an uncharted grey area. Take the infamous Canadian tux faux pas: When then-lovers Justin Timberlake and Britney Spears thought it was a cute idea to wear full-on denim to the 2001 American Music Awards. Nearly two decades later, the wince-inducing aftertaste still lingers. But care to backtrack just a few years from the denim debacle, and you’ll enter the golden era of couple dressing.

Remember the Winona Forever epoch? Before alternative was an overly used adjective, ’90s Winona Ryder was the exact epitome of it. Pair her up with ’90s Johnny Depp and you have the ultimate alternative-cool couple. Take flash-lit pap shots of the brooding duo, and there you go, the most sophisticated oh-are-we-twinning lookalikes. Think: Tons of chic black, creased tees, tousled wavy curls. Only, of course, you don’t have to go to great lengths to dream that up, because that did actually happen.

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’90s throwback: Johnny Depp and Winona Ryder, in sync in their black-white louche tailoring.

Following a maelstrom of effortless-chic Victorian goth looks post-Edward Scissorhands, the engaged couple called it quits in 1993. Depp then swiftly moved on to his next best couple dressing match: It-model of the time, Kate Moss. For the next four years, the impossibly attractive lovebirds were gossip tabloid fodder in their beaten-up vintage biker jackets and aspirational bed hair.

Another chic couple who nailed wardrobe- and hairstylist-sharing right was, never forget, Gwyneth Paltrow and ex-fiancé Brad Pitt. The all-American blond-streaked duo was the country’s power couple of the mid-’90s. Despite not working things out in the relationship department, one thing was for sure: They took twinning to a whole new height of seriousness. Stepping out for a movie premiere in 1997, Paltrow and Pitt came arm-in-arm in rivalling slick, side-parted, chin-length ‘dos.

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Former fiancés Gwyneth Paltrow and Brad Pitt shared more than just the other’s closet.

There’s a psychological explanation to why a majority of people tend to be attracted to those resembling themselves. According to another study, couples usually start to adopt similar styles six months into a relationship, often times subconsciously, as they go through the same experiences. Emotional face-mirroring is deemed to be a gauge, too. Scientific fact: The happier a couple are, the more they mimic each other.

But while celebrity couple dressing history doesn’t exactly make the strongest case for “couples who dress together, stay together” hypothesis, there’s also Victoria and David Beckham to consider. The high-profile, modern-day love story that’s a tale as old as time. Attraction at first sight — in a half-tipsy bar situation, naturally; followed by the hearts-and-flowers phone number dropping; and well, the rest was history peppered with coordinations of chic replicas.

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There’s a reason why Posh and Becks are one of the best dressed couples of all time

If Posh and Becks have convinced you enough to shake off the universally acknowledged exasperation towards couples who intentionally dress alike, here’s what you and your partner need to know before giving the doppelgänger path a try. Mastering the art of matched dressing requires equal parts nonchalance (i.e. the too-cool-to-care air of Depp-Moss, Depp-Ryder etc) and well-calculated subtlety (i.e. almost-accidental matchy-matchy looks of Pitt-Paltrow, Posh-Becks etc). The general rule of thumb is to stick with easy, classic pieces and colours.

Black tailored blazers, yes. Head-to-toe denim, no. Baggy sweaters in muted tones, yes. Polka dot party, no. You get the gist. Easy does it.

(All images: Getty)