How your favourite 1999 rom-coms predicted 2019’s biggest fashion trends

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Billie Bhatia
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Twenty years ago saw the ultimate peak in fashion and film. To be honest, we haven’t been able to get over it since. 

Here’s the scenario: It’s Sunday, it’s been a tough week, your plans got cancelled (praise be) which means actually you can fulfil the prophecy you’ve been thinking about all week: to sit in front of the TV with some kind of comfort food and watch a romantic comedy.

You’ve spent 30 minutes scrolling through Netflix, Amazon Prime, Sky and [insert other entertainment platform here] to find the perfect one. That ‘perfect one’ being a film that consists of all the magic romcom ingredients: strong female lead, attractive male counterpart, a hilarious best friend, a wardrobe that evokes both joy and desire, and most importantly a happy bloody ending.

You’ve been scrolling so long you think about giving up on the Sunday dream and just watching an episode of Friends. In a final bid to find ‘the one’ you scroll right back to the beginning of your search and gamble your Sunday happiness on a fresh release that people at work have said is ‘worth a watch’.

You’re not sure about it but the clock is ticking, your mac and cheese is now congealed, and you want to wrap this up in time for a face mask and a bath.

Click and go.

The end credits roll and you’re raging. This 2019 film didn’t even come close to hitting the ‘Sunday fuzz’ spot that you so desperately wanted. There was no ugly cry, no snorts of laughter, no ‘I wish I wore that dress to prom’, no ‘please meet her on the baseball field and kiss her’. In short, it’s a total bloody waste (I’m looking at you Isn’t It Romantic). So much emotional investment, so little outcome.  

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It’s 2019, and you’d think the world would know by now what kind of rom-com we need, right? Wrong. I’ll tell you what we need. We need 1999. The holy grail of rom-coms and the pinnacle of fashion and film. Don’t believe me? I’ll even break it down for you.

The big hitters: Never Been Kissed, 10 Things I Hate About You, Notting Hill, Cruel Intentions, She’s All That and Runaway Bride.

The lesser known but still tick the box: Drive Me Crazy, Simply Irresistible and Three To Tango.

Whilst it has been 20 years since this level of rom-com magnitude has hit our screens, the style in these films is timeless. In fact, no, they are so spring summer 2019 (and beyond) they might as well have been released this year. 

Don’t believe me? Let me explain…

Never Been Kissed

What we wouldn’t give to haveJosie Geller’s white feather-trimmed shirt (the one that she dropped her lunch tray down) in our wardrobes right now. Or her high-waisted dark denim with square neck top, as styled while casually reclining on the bleachers. Even her so-Eighties-it-hurts metallic pink prom dress could be mistaken for Gucci if paired with the right accessories (sorry Josie, we aren’t taking the side ponytail with us). And, of course, let’s not forget the piece de resistance: the pink ruffle neck, capped sleeve, ditsy print midi dress that we would wear to every wedding and beyond. 

10 Things I Hate About You 

Cool kid Kat has every Nineties trend nailed in one film: the sad sonnet slip skirt, the spaghetti-strap slip dress (again, we pass on the hair), the platform flip flops she insists on wearing pretty much the entire way through the film, and her camo printed vest. We’ll take the lot. 

Notting Hill 

Anna Scott is the girl standing in front of our screens asking us to love her… wardrobe. And it all began with the coupling of a black beret and a pair of tiny sunglasses: if that isn’t SS19 we don’t know what is. 

Let’s get one thing clear, Anna Scott is much, much cooler than the rest of us. Not only does she wear a leather blazer instead of a leather jacket (excuse me as I Google said black leather blazer), but she also knows how to knock jeans and a nice top out of the park… right into a private garden. 

She’s All That 

Usher as the school DJ, Paul Walker as the bad boy jock, Freddie Prinze Jr declaring he can make any girl prom queen, and the ‘wow’ moment of the film set to Six Pence None The Richer’s ‘Kiss Me’. Yup, She’s All That knows how to do a Nineties rom-com. If you haven’t walked down the stairs in a red dress, then you took nothing away from this film but the knowledge that you will never know why a hacky sack is called a hacky sack. From Matthew Lillard’s shell necklace, to the mean girl’s halter neck crop tops - this summer we aim to be more ‘all that’. 

Cruel Intentions 

Of all these 1999s film, Cruel Intentions is arguably the chicest. Leave it to the Upper East Side’s step-siblings to still be playing out our fashion fantasies 20 years after all the backstabbing and bed-hopping hit our screens. Whether you were Team Kathryn in a dark plethora of silk sultry dresses and Dolce & Gabbana corsets, tailored suiting, or preferred to channel good girl Reese Witherspoon in a light lilac jumper and skirt (and general angelic aura), one thing is for certain: we all wanted a gothic cross necklace after this film. 

Runaway Bride 

Roberts strike again, this time as the bride that can’t quite make it down the aisle. That is until she meets Richard Gere (for the second time in her rom-com career) and takes on a tie-dye top, cowboy boots and a bevy of wedding dresses we would gladly walk down the aisle in now. 

We could go on, but we know you’re itching to hunker down and have a binge on Hollywood’s most fashionable year. Enjoy!

Images: Rex Features / 20th Century Fox / IMDB / Instagram