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Chris Pine’s ‘I Heart LA’ shirt for Poolman – and 4 more chaotic looks

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Most recently, the 43-year-old took “method dressing” to another level when he arrived at the premiere of his directorial debut Poolman dressed as his character Darren Barrenman, in Los Angeles, on April 24. The, erm, eclectic ensemble was made up of an “I Heart LA” T-shirt under a blazer and shorts accessorised with a pair of hiking boots and mirrored sunglasses. His long stringy hair extensions added to his tousled look.

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In an interview with People in October 2023, the “silver fox” summed up his fashion sense with one enigmatic word: “jiggy”.

Here’s a look at some of his most iconic ‘fits so far.

1. “Big Boy” tank

The Don’t Worry Darling star made his way to a morning dance class in October wearing a “Big Boy” tank top – apparel from a US restaurant chain – with black shorts over a pair of black tights. He finished the look with a simple baseball cap.

2. Sweater weather

Also last October, Pine rocked the unshaven look complete with bedhead with what appeared to be a random assortment of autumn-friendly attire: a rainbow-striped cardigan, black leggings under a pair of short shorts, and a simple tank. Oh, and a coffee in hand.

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Thrown together or not, the outfit’s “chaotic” cardigan, by the way, costs US$2,395 from The Elder Statesman, per CNN Style.

3. Boat day out

Last summer, in August, Pine was spotted enjoying the yacht life with a “mystery woman” in Sardinia, Italy, states British media. For this leisurely outing, he rocked a pair of super-short teal shorts (we’re sensing a trend here …) and was later seen strolling the beach in one easy-breezy accessory also loved by Brad Pitt: a bucket hat.

4. “Pyjama” outing?

Chris Pine at Jimmy Kimmel Live in 2023 in Los Angeles, California. Photo: GC Images
Last March, Pine was spotted casually strolling the streets in what looked to be a very comfortable set of beige silk pyjamas. He wore the half-unbuttoned shirt and pants combo on his way to film an appearance on Jimmy Kimmel Live in LA while promoting his new film Dungeons and Dragons: Honor Among Thieves, per JustJared.
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