Times Brooke Shields' Daughters Wore Her Old Looks (And Totally Rocked Them)

While Brooke Shields is most known as an actor, model, and fashion icon, she's also a doting mother to two daughters. If you're unfamiliar, her oldest daughter, Rowan Francis Henchy, was born in 2003, while her second daughter, Grier Hammond Henchy, was born in 2006. Shields shares both children with her husband, the movie producer and screenwriter Chris Henchy, who she's been married to since 2001.

The celeb's professional and personal worlds have collided several times over the years, with her daughters shopping through her vintage clothing to don some of her most memorable looks. "It's funny — my older one will borrow her dad's sweater. That's it," Shields says about her daughters. "Sometimes my shoes, because we have the same shoe size, but she doesn't do any borrowing really. The other one's got Velcro hands" (via People).

Though the NYC native stuns in anything she wears, Grier and Rowan have equally rocked Shields' vintage looks in their own unique ways. From her 1998 Golden Globes gown to her Dolce and Gabbana "Suddenly Susan" suit, here are all our favorite times Brooke Shields' daughters rocked her old looks.

At the opening night of "Previously Owned by Brooke Shields," a theatrical event hosted at the Café Carlyle, Grier Henchy stunned in a vintage dress from her mother's wardrobe. The Badgley Mischka look was originally worn by Brooke Shields back in 2001 at Marshall Field's Fash Bash hosted at the Chicago Theater.

Shields featured these twin occasions on her Instagram, posting side-by-side photos of her and Grier in the Badgley Mischka dress. "Two of my most favorite recent moments ... each 22 years apart," the model captioned the post, referencing a second throwback fashion moment. "This week Grier wore my @badgleymischka dress from 2001 to my @cafecarlyle premiere!!"

The beautiful, floor-length gown, which features sparkly beading, lace detail, and a square neckline, was paired with simple silver heels worn by both women. While Shields styled her hair in a half-up look, her daughter went for a loose, slightly wavy 'do. Grier's look was an ode to her mother's fashion prowess, but she definitely managed to impress in her own way.

Back in June of 2021, Rowan Francis Henchy wore one of her mother's most iconic dresses for her prom night, which we're sure was an absolute dance-floor dazzler. Brooke Shields first sported the red satin gown at the 1998 Golden Globes. At the time, the celeb was nominated for Best TV Actress for her role in the NBC sitcom "Suddenly Susan."

The "Pretty Baby" star honored her daughter's special night with an Instagram post featuring a snapshot of the two embracing and a photo of Rowan mimicking her mother's 1998 akimbo pose. "I thought it was a special night when I was nominated for a Golden Globe and wore this dress in 1998," Shields wrote. "But nothing could have prepared me to see my daughter wearing it to her prom ... proud mama!"

While the actor styled her look with a matching satin shawl, an old Hollywood glam hairdo, and a bright red lip, her daughter went for a more subdued look. In lieu of the gown's shawl, Rowan paired the dress with a black designer handbag, a gold cuff bracelet, and a loose, wavy hairstyle. Even if Rowan doesn't borrow from her mother often, she absolutely kills it when she does. 

Grier Henchy also honored Brooke Shields at the premiere of her "Pretty Baby" documentary in March 2023. The young model donned an eye-catching Dolce and Gabbana suit that was worn by her mother on NBC's "Suddenly Susan." As Susan Keane, Shields wore the bright red ensemble in Episode 11 of Season 1, though only for the final two minutes of the episode.

You can catch some snapshots of Grier in the Dolce and Gabbana look on Shields' Instagram, as she posted a handful of photos from her documentary's premiere. "Full of gratitude. Full of excitement. Full of love," she shared. "NYC Premiere of #PrettyBaby last night!!"

While the sitcom star originally wore the pantsuit with her classic loosely tousled hairdo, a gold broach, and a simple beaded necklace, Grier modernized the outfit with shiny black heels, a sleek ponytail, and a gold clutch. We love the outfit on Shields, but we're obsessed with her daughter's styling.