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Naomi Campbell -

Walking around Paris in 2021, the supermodel looked effortlessly cool wearing black leggings with an oversized shirt, bomber jacket, and combat boots.

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Kim Kardashian -

Kim K went for a comfy burgundy look while out in New York in 2021.

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Tessa Thompson -

The actress looked super warm and comfy at the 2020 Sundance Film Festival. Definitely a look worth copying for those cold winter months.

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Rihanna -

By adding a pair of golden boots with an oversized tee and jeans, Rihanna shows she knows very well how to amp up a casual look. It was the perfect look while she strolled around New York in 2021.

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Hailey Bieber -

Spotted in LA in 2021, the model is a major fan of oversized looks. With the leather jacket, cap, and blue jeans, she's the reincarnation of the '90s 'it' girl.

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Zendaya -

Bedazzled from head to toe at the London photocall for 'Spiderman: No Way Home' (2021), Zendaya looked far from casual with her oversized blazer.

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Kendall Jenner -

Out in New York in 2021, Kendall Jenner wore a classic white shirt with her beige chinos. It was both a casual and elegant look.

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Billie Eillish -

The queen of oversized clothes wore a monochromatic look to the 2021 Variety Hitmakers event. That coat looks cozy enough to fall asleep in!

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Bella Hadid -

The model was another one wearing a '90s-inspired look, this while out in New York in 2021.

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Celine Dion -

Seen out and about in New York in 2020, the iconic singer paired two oversized pieces: the jumper and skirt. Talk about flower power!

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Emily Ratajkowski -

The model walked the streets of New York in 2021 looking mega classy (and classic).

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H.E.R. -

The singer proved that an all-denim look is the way to go, especially with an oversized flare. Definitely a cool look for her visit to The Elvis Duran Z100 Morning Show in 2019.

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Gigi Hadid -

The model not only went oversized with her jacket, but also with her hat! She wore this cozy creation in the cold streets of Paris in 2021.

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Jennifer Lopez -

J.Lo was all shades of blue while out in LA in 2021. She rocked a pair of baggy jeans, a baby blue coat, and a matching bag.

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Lady Gaga -

Out in New York in 2021, Lady Gaga was working a casual rocker look with her oversized blazer, ripped jeans, T-shirt, and classic Gaga boots.

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Tracee Ellis Ross -

Spotted at the WIRED25 Summit 2019, the actress wore a classic gray suit, but kept it fun with a patterned shirt underneath.

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Yara Shahidi -

Strolling around New York in 2020, actress Yara Shahidi added some color with her floral printed coat and matching heels. Talk about a proper spring coat!

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Demi Lovato -

Demi was pure coolness with their leather coat and blue accessories, showing us how a true star walks the streets of New York, this in 2021.

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Ciara -

Ciara's outfit was a showstopper at the 2020 NFL Awards. Paired with simple heels and a purple clutch, this outfit is perfect party attire.

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Halsey -

Never shy when it comes to fashion, Halsey went for an oversized white with neon patterns skirt at the 2019 ARIA Music Awards.

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Rosie Huntington-Whiteley -

The model added a pop of color with her oversized blazer at the Create & Cultivate event in New York in 2019. 

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Selena Gomez -

Out in New York in 2020, Selena Gomez was all comfortable chic with her matching outfit. To keep it interesting, she matched her sneakers with her hoops, and added a dark lip for some drama.

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Maya Rudolph -

Here at the 2020 Academy Awards, the former 'SNL' star had a true fashionista moment with her shimmery orange dress.

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Vanessa Hudgens -

Going for a more tropical look, the actress attended the LA screening of 'Tick, Tick... Boom!' (2021), matching her shorts and jacket.

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Rosalía -

The Spanish singer went for an all-black look, topped with a white cap, while strutting around New York in 2021.

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Katie Holmes -

Seen running errands in New York in 2020, the actress was pure comfort wearing baggy jeans and an oversized cropped-jacket.

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Emma Roberts -

The actress looked effortlessly classic out in LA in 2018. With matching trousers, shades, and a pair of white retro boots, this was a totally cool look.

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Zoey Deutch -

The actress looked like a true '80s businesswoman with her oversized blazer at the Celebrities Visit Build event in 2020. She kept it interesting with the blue and white patterns, and those white heels.

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Joey Soloway -

At the Golden Globe Ambassadors party in 2019, the 'Transparent' creator proved that red carpets can also be comfortable with a suit and cool sneakers.

Sources: (Vogue) (Slice) (Grazia)

See also: The best celebrity cardigan moments

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