Debra Messing has never been afraid to embrace a swimsuit moment, and as she celebrates her 58th birthday, her collection of vacation photos proves her confidence has only grown with age.
The Will & Grace star has shared plenty of sun-soaked snapshots over the years, from glamorous poolside selfies to carefree days spent on the water, but one throwback takes us all the way back to her teens.
Long before she became one of television's most recognizable redheads, Debra was an 18-year-old with dreams of becoming an actress, and the gorgeous vacation photo shows just how little she's changed.
Debra Messing at 18
In the nostalgic snap, Debra looks radiant in a black printed bandeau bikini while enjoying a family vacation on a cruise ship.
Wearing her naturally curly brunette hair short, the future star beams at the camera as she poses on deck, giving no hint of the Hollywood career that lay ahead of her.
Sharing the photograph decades later, Debra revealed just how significant the trip had been.
"Going through old boxes from storage and came upon this picture of me from when I was 18. I remember that family vacation vividly. We laughed the whole time," she wrote on Facebook.
"I sang in the passenger talent show, telling everyone that I wanted to be a professional actress. I see a girl filled with joy and hope. I'm grateful for her dreams and self belief."
It's a particularly poignant photo knowing that the teenager pictured would go on to make those ambitions a reality, finding global fame as Grace Adler on Will & Grace and earning an Emmy Award for the beloved role.
Debra Messing in Along Came Polly
In 2004, Debra showed off her incredible figure on screen in the romantic comedy Along Came Polly, in which she played Lisa Kramer opposite Ben Stiller.
The tropical scene sees Lisa enjoying her honeymoon in St. Barts in a red-and-white patterned bikini with coordinating trousers and an open white shirt, shortly before her ill-fated scuba-diving excursion.
The role came during the height of Debra's Will & Grace fame and showed a very different side to the actress, with Lisa's glamorous honeymoon wardrobe a far cry from Grace Adler's polished New York style.
Bikini beauty
Debra has continued to embrace swimwear away from the cameras too, sharing a striking selfie in a classic black halterneck bikini while relaxing on a striped sun lounger.
With her hair swept into a relaxed bun and oversized sunglasses completing her poolside look, the actress looked effortlessly glamorous as she soaked up the sunshine.
The timeless black two-piece is a style Debra has returned to over the years, proving that sometimes the simplest swimwear makes the biggest impact.
Poolside glamour
In another gorgeous photograph, Debra showed off a different side of her vacation wardrobe in a pale blue one-shouldered swimsuit.
The asymmetric design was accessorized with layered gold necklaces, oversized sunglasses and a wide-brimmed sun hat as she posed beside a swimming pool surrounded by lush greenery.
Another shot saw her reclining in the same swimsuit without the hat, her famous red hair pulled back as she soaked up the sunshine.
Fun on the water
Debra looked equally fabulous during a tropical boat trip, opting for a black swimsuit with a skirted silhouette as she took the helm against an idyllic backdrop of turquoise water and palm trees.
The actress appeared completely in her element as she sat barefoot on the boat, her red hair blowing in the breeze.
And the water clearly holds a special place in Debra's heart, with another vacation snap capturing her sitting aboard a boat at sunset in a black swimsuit as the sky turned spectacular shades of orange and gold behind her.
Celebrating another trip around the sun
Debra also marked a previous birthday with a memorable day spent on the water with her son and friends.
"What a Day," she wrote alongside photos from the celebration. "Ocean air, my son, some friends, cocktails, cake, water toys, dinner (not shown) and a lovely (?) happy birthday from a boat full of passing revellers as the fuschia exploded across the sky."
She added that although it "wasn't a 'special' birthday," messages from people throughout different chapters of her life had left her feeling "loved and humbled."
For the occasion, Debra wore another flattering black swimsuit as she climbed aboard a boat, accessorizing with oversized shades and wearing her hair piled into a carefree bun.
Swimsuit confidence in her 50s
One of Debra's most striking recent swimsuit photos came during a solo trip to Iceland, where she took a dip in the country's famous milky-blue geothermal waters with her hair piled into a messy bun and seemingly little to no makeup.
But behind the serene image was a much more emotional story. Debra revealed that she had travelled alone after feeling overwhelmed by the "hate and violence" she was seeing around the world and admitted she had been left feeling "impotent. Heartbroken. Enraged. Overwhelmed."
"Sometimes you just have to run away," she wrote, explaining that she realised she "needed to reset" and chose Iceland because "the majesty of Nature is always the answer for me."
The trip proved transformational. After witnessing the Northern Lights and venturing inside a glacier, Debra said the experience had given her a new perspective.
"I felt like I was on another planet," she wrote of the glacier adventure, while seeing the Northern Lights reminded her of "the Awesomeness of the Universe" and "brought me back to life."
