Elegant layering comes naturally to VIP New Yorkers. See Katie Holmes, for instance. The street style star has always been able to layer up without looking bulky, a skill she brought with her to the American Ballet Theatre's 2026 Spring Gala on May 20. She gave the dress-over-pants trend a prima ballerina makeover by stacking a mini dress on top of a matching skirt.
Being one of ballet's biggest supporters, it's no surprise Holmes has rarely missed an American Ballet Theatre gala since 2017. She joined celebrities, sponsors, and ballerinas alike at Midtown Manhattan's Cipriani 42nd Street, though she looked ready for an evening at Lincoln Center. Stylist Brie Welch got her hands on Look 33 from the Ashlyn Spring 2026 show for her star client.
What started as a plunge, spaghetti-strap mini required some sartorial courage. To no surprise, Holmes pulled off the Swan Lake-white dress with ease. The New York-based label designed its crinkled, thigh-high hemline to be worn over a matching maxi skirt, though. Holmes understood the assignment and pulled the slightly-less-flouncy slip up to her hips.
The same unironed fabric stretched onto Holmes's second, ankle-grazing skirt. It was fashioned into more of a bubble silhouette, curving outward around her thighs. Picture the barrel jeans trend she adores for mid-afternoon errand runs, but make it center-stage ready.
Ashlyn's model styled black leather opera gloves behind the voluminous skirt set, but Holmes opted out. Her only accessories? A statement collar-style necklace, coordinating diamond earrings, and Herbert Levine's take on the heeled flip-flops trend. The New York-based brand has been behind some of her buzziest shoes this season. Last month, she tapped into the high-vamp heels trend with help from the same label.
Sure, Holmes could've worn the Ashlyn mini on its own with pink tights fit for the barre. But that wouldn't have been nearly as on-brand. Her unlikely layered looks have been turning heads for years. The Dawson's Creek star's most viral moment came in Dec. 2022, when she walked the iHeartRadio Jingle Ball red carpet in a satin mini dress and straight-leg jeans. It's worth mentioning she referred to the royal blue bodice as a "corset," though.
"I felt cool, I felt great, and then I woke up the next morning and I was like, 'Oh my gosh,'" Holmes told Drew Barrymore in 2023, after the dress-over-pants set made headlines.
As recently as Nov. 2025, Holmes gave the divisive duo another chance with help from a different NYC designer, Attersee. First, she slipped on a $795 pair of baggy, charcoal-gray trousers. Then, she clasped a structured, silk-wool blend shift dress over the high-rise waistband. Vertical darting and cascading hook-and-eye closures kept the neutral color story interesting.
The concept of "too many layers" doesn't apply in Holmes's look book. She's never been intimidated by multiple pieces. In fact, her outfits almost feel incomplete without at least a couple tiers. The season of less and less layers is fast approaching, but trust: Holmes will find a way to keep packing them on. Whether that be with sheer styles, summer crochet, or another nod to the corps de ballet is up to her.
