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He made a second fortune after selling a tequila label he founded with his friend Rande Gerber.
George Clooney, 58, and his wife Amal Clooney, 41, were spotted out on Thursday night in New York City as the couple joined Rande, 57, and his wife Cindy Crawford, 53.
The friendly couple went out to the swanky steakhouse 4 Charles Prime Rib to celebrate George and Amal’s fifth wedding anniversary a day early.
On the town: George Clooney, 58, and his wife Amal Clooney, 41, were spotted out on Thursday night in New York City as the couple joined Rande Gerber, 57, and his wife Cindy Crawford, 53
Despite the celebratory nature of the dinner, George stuck with a low-key casual look for the outing.
The Out Of Sight star had on a navy blue button-up shirt with short sleeves and a pair of baggy acid-wash jeans.
He sported a set of gray suede shoes and displayed a bushy salt–and–pepper beard.
George and his wife had their hands locked as they strolled up to the restaurant.
No fuss: Despite the celebratory nature of the dinner, George stuck with a low-key casual look for the outing
Blue mood: The Out Of Sight star had on a navy blue button-up shirt with short sleeves and a pair of baggy acid-wash jeans
Fuzzy face: He sported a set of gray suede shoes and displayed a bushy salt–and–pepper beard
Loving couple: George and his wife had their hands locked as they strolled up to the restaurant
Amal looked effortlessly stylish in a pair of loose-fitting high-waisted black leather pants by Philosophy di Lorenzo Serafini.
The outfit featured prominent white stitching and a thick leather belt, which she tied in a knot around her waist.
The human rights barrister mixed the pants with a frilly white dotted Philosophy di Lorenzo Serafini top that showcased her fit arms and slender shoulders.
Her brunette locks cascaded elegantly down her back, and she completed her look with a thick clutch in red, gold and black.
Style icon: Amal looked effortlessly stylish in a pair of loose-fitting Philosophy di Lorenzo Serafini high-waisted black leather pants
Edgy: The outfit featured prominent white stitching and a thick leather belt, which she tied in a knot around her waist
Svelte figure: The human rights barrister mixed the pants with a frilly white dotted Philosophy di Lorenzo Serafini top that showcased her fit arms and slender shoulders
Lustrous locks: Her brunette tresses cascaded elegantly down her back, and she completed her look with a thick clutch in red, gold and black
Towering: She elevated her 5ft9in stature with a pair of tall black heels
Cindy Crawford stuck with a fairly reserved look, wearing a silky ruched blouse under a dark blazer that she wore over her shoulders.
The 5ft9in supermodel completed her outfit with a pair of black slacks and black open-toe heels.
Her caramel-colored locks were styled in waves that framed her face and revealed her silver hoop earrings.
Reserved style: Cindy Crawford stuck with a fairly reserved look, wearing a silky ruched blouse under a dark blazer that she wore over her shoulders
Back in black: The 5ft9in supermodel completed her outfit with a pair of black slacks and black open-toe heels
Rande looked as if he’d coordinated with George on his outfit. He wore a navy blue button-up shirt similar to his friend’s, as well as jeans.
He added a touch of class with a matching blazer, though his black sneakers kept the look low key.
Rande and George shared a hug once the two couples met up, and they stopped to chat outside the restaurant.
The two pals, along with property developer Michael Meldman, founded Casamigos Tequila in 2013 after sampling a variety of tequilas while building vacations homes next to each other in Cabo San Lucas, Mexico.
The investors initially put in $600,000 a piece. By 2017, Diageo, the world’s largest spirits manufacturer, purchased the company for $700 million, with an extra $300 million available if the brand sold well over the next decade.
Considering their close friendship, Rande and Cindy made an ideal couple to help George and Amal celebrate the anniversary of their wedding five years ago.
Look-a-likes: Rande looked as if he’d coordinated with George on his outfit. He wore a navy blue button-up shirt similar to his friend’s, as well as jeans
Old friends: The tequila founders shared a hug once the two couples met up, and they stopped to chat outside the restaurant
The friendly gathering was in honor of George and Amal’s fifth wedding anniversary.
The Ocean’s Eleven actor got engaged to the British-Lebanese lawyer on April 28, 2014.
The couple tied the knot in a palace in Venice, Italy, on April 27, 2014.
Absent from the adult outing were George and Amal’s young twins, Ella and Alexander, both two.
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