Bridget Moynahan's Stunning Style Transformation, In Photos

Bridget Moynahan has spanned years of fame in top-class style. She first broke out onto the scene as a model and later switched to acting. She became famous for her role as Natasha Naginsky in "Sex and the City," marrying Mr. Big and ultimately divorcing him because of his affair with Carrie Bradshaw. From this breakout role, Moynahan launched a successful career with roles in "Coyote Ugly," the "John Wick" series, and "Blue Bloods." 

Moynahan's personal life also became a hugely sensationalized topic. She dated football legend Tom Brady from 2004 to 2006. They broke up and Brady began a relationship with Gisele Bündchen; it was only shortly after this that Moynahan discovered that she was pregnant with Brady's child. She raised her son, Jack, as a single mother with the challenge of tabloid gossip making much of Brady's departure for Bündchen. Incredibly, it was clothing and style that played an important part in Moynahan's ability to move on from the drama. She co-authored a book called "Our Shoes, Our Selves," in which Moynahan described the paparazzi attention surrounding her while she was pregnant. To cope, Moynahan bought a pair of black leather Miu Miu motorcycle boots that acted as her armor. In fact, Moynahan went through an epic transformation after her split from Brady. Since these shoes functioned as an important part of Moynahan's ability to carve out her own life, it's no wonder that much of her public persona has centered on her fashion and her incredible style overhaul. 

Bridget Moynahan first became famous in the early 2000s and her style reflected this. When she attended the premiere for "High Fidelity" on March 28, 2000, in Hollywood, California, she wore a knee-length leather skirt, leather boots, a cropped print top and a denim jacket. It was peak 2000s style and has come full-circle. Moynahan's outfit easily makes the list of early '00s celeb outfits we'd actually wear today. She completed the look with a black choker, making the fit an impeccable example of Y2K style. 

Bridget Moynahan obviously had that star quality from the start. When she attended the premiere of "Coyote Ugly" on July 31, 2000, she showed up in a black halter top dress with a plunging neckline. The handkerchief hemline, another key feature of Y2K fashion, was absolute perfection on this simple-yet-sexy look. She completed the dazzle with a pair of sleek, strappy black heels and a slick bun.

Bridget Moynahan was all smiles when she attended the Vanity Fair Oscar Party on February 27, 2005, with boyfriend Tom Brady. Moynahan wore a plunging forest green gown with no jewelry, keeping the focus on her sculpted décolletage. Moynahan's hair was also having an evolution of its own. She wore her hair in a fluffy shag cut with short bangs. It was a fresh take on her previously longer hair. 

Bridget Moynahan took a page out of Audrey Hepburn's style book when she attended a screening of "Gray Matters" in New York on February 15, 2007. She wore her hair in a glossy side-parted bun with statement earrings. Pregnant at the time, she donned a drop-waist black dress with a voluminous short skirt and completed the look with sheer black tights and black pumps. Moynahan's style was evolving into a more sophisticated and glamorous presence on the red carpet compared to her taste in 2000.

Bridget Moynahan and Tom Brady split in December 2006. Shortly after, she discovered that she was pregnant with Brady's child, and in February 2007, she confirmed with the press that she was going to have a baby. So Moynahan embarked on pregnancy as a single mom. She showed off her incredible maternity style at a Coach Fragrance Launch to Benefit EBMRF in Los Angeles, California, in April 2007, with Gretchen Mol. Moynahan wore a gray wrap dress with blue and white flowers, and looked fresh and radiant. 

Bridget Moynahan absolutely killed it when she attended the CFDA fashion awards in New York on June 2, 2014. She wore a fuchsia strapless gown with a dramatic train, and she swept back her hair into an elegant updo. Moynahan's style evolution was clear at this event. Instead of wearing black dresses or simple outfits — as she had previously done on red carpets — she was taking up space and making sure the spotlight was on her. We love to see a diva's aura come through.

Bridget Moynahan married businessman Andrew Frankel on October 17, 2025, in Sagaponack, New York. Moynahan's marriage to Frankel is full of green flags, and after the disappointment of her relationship with Tom Brady, her happy marriage is such a win. So when Moynahan attended the American Heart Association's Go Red For Women Red Dress Collection on February 9, 2017, she looked like a dream in her fitted red gown. Love, clearly, looks good on Moynahan.

Bridget Moynahan slipped into something a little more simple than the gowns she had donned in previous years when she attended the Brandon Tartikoff Legacy Awards on January 17, 2018, in Miami Beach, Florida. She wore a stunning raspberry-toned cocktail dress with sheer lace detailing along the neckline and sleeves. Moynahan finished off the look with black shoes that had a bejewelled decal. She looked sleek and sophisticated, while her soft curls added a touch of romance to the outfit. 

Bridget Moynahan looked cool as a cucumber when she attended day three of the US Open Tennis Championships in Flushing Meadows, Queens, on August 26, 2025. Moynahan wore a monochromatic outfit featuring wide leg trousers in cream with a tonal sweater wrapped around her waist. She wore a white t-shirt and tinted aviator glasses as well as white sneakers. Her chic, off-duty look was the perfect fit for the sporting event, and Moynahan proved her range with the stylish outfit.

Bridget Moynahan stepped out in a whole new style for her when she attended the Cantor Fitzgerald Relief Fund in New York on September 11, 2025. She wore tailored dark slacks with a crisp button-down shirt and a tie. Her experimentation with menswear, something vastly different from what she typically wore, totally paid off. It was proof that Moynahan's winning style is always transforming thanks to her willingness to experiment with something new.