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STYLE | Fashion

Gen-X, Millennials and Gen-Z date night looks

Stylish fits from our favourite films from the 90s to today

By Lena Kamarudin - 

Drew Barrymore in Never Been Kissed (1999)
Drew Barrymore in Never Been Kissed (1999)
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Date night looks don't always have to be the predictable combo of a pretty dress with heels. In fact, who said that you had to wear a dress or skirt for a date? The key is to look and feel confident and comfortable so wear whatever that rocks your fancy.

And since, the Y2k trend is still hot on the fashion barometer, we took inspo from some of our leading ladies in our fave rom-com movies then and now. And if you've not watched any of these movies listed here, this is your chance to get cosy on the couch and grab a popcorn with that special someone.

Pretty cool way to end the night don't you think?

Millennials: The Notebook (2004)

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The film was set in the 1940s so Rachel McAdams's character Allie Hamilton had a wardrobe full of pretty vintage dresses accompanied by accessories such as pearls and Maryjane pumps.

Gen Z: The Perfect Date (2019)

Credit: Netflix
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Celia Liberman is a high-school student played by Laura Marano. Her cute getups include that tutu dress and biker jacket getup she wore on the "set-up" date which is what the film revolves around.

Millennials: How to Lose a Guy In 10 Days (2003)

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The most famous outfit Kate Hudson wore in the movie was the slinky yellow dressbut her on-screen persona Andie Anderson's off-duty style is a mix of elevated basics with an androgynous vibe.

Gen-X: Drew Barrymore in Never Been Kissed (1999)

Credit: Getty Images
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Recreate Drew Barrymore's character Josie Geller quintessential ’90s outfits made up cute candy floss-coloured dresses, pretty floral cardigans and feather-trimmed tops

Gen-Z: To All The Boys I Loved Before (2018)

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Lana Condor's preppy-inspired fits consisted lots of mini skirts and long-sleeved tops paired with sneakers.

Gen-X: 10 Things I Hate About You (1999)

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Cropped tops and low-waist jeans were Julia Stiles's feisty character Katherine (Kat) Stratford's "uniform".

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drew barrymorefashionhollywood celebritiesSingapore
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