Brooke Shields Gave A Layering Masterclass At Tommy Hilfiger’s NYFW Show

Given the style set usually spends August on various enviable vacations, it comes as no surprise that it’s a quiet month on the fashion front. However, once September rolls around, the celebrity circuit springs back into action. New York is an especially buzzy hotspot, thanks in part to the US Open and New York Fashion Week, of course. And the Spring/Summer 2025 show season is no different. On Sept. 6, the first portion of fashion month started strong, as style muses like Rihanna, Naomi Watts, Tracee Ellis Ross, and Ciara (just to name a few) touched down in the Big Apple.

Even though NYFW didn’t officially commence until Friday, the fashionable fêtes kicked off a few days ahead of schedule (a classic Fashion Month move). Just 12 hours before the first official show began, Ralph Lauren hosted the likes of Laura Dern, Joey King, Dr. Jill Biden, and more in the Hamptons — a three-hour trip away from the hubbub of Manhattan. The next day, Rihanna made a surprise appearance at the Guggenheim Museum for the Alaïa Spring/Summer 2025 show, dressed in a custom corseted look from the iconic atelier. Fast forward to Sept. 8, when editors, influencers, and A-listers boarded the MV John F. Kennedy (a former Staten Island Ferry boat) for Tommy Hilfiger’s nautical-inspired presentation on the water. Brooke Shields, Winnie Harlow, and Madelyn Cline posed aboard the Colin Jost- and Pete Davidson-owned boat in a classic Americana attire. All this to say? Unexpected venues are the biggest trend of NYFW.

But wait — that’s not all. The week-long affair runs until Sept. 11, so bookmark this page for the best celebrity outfits from NYFW S/S ‘25 edition. And keep scrolling for TZR’s favorite moments so far.

Brooke Shields

On Sept. 8, TZR cover star turned heads onboard the M.V. John F. Kennedy wearing an assortment of autumnal must-haves. Shields posed in a white button-down, a plaid mini skirt, a khaki trench coat, and knee-high boots — all sourced from Tommy Hilfiger.

Winnie Harlow

The model looked ready to also attend the US Open in her Americana-inspired Tommy Hilfiger ensemble, complete with a pinstripe mini dress and a tied trench coat. She dressed it down via a burgundy baseball cap.

Madelyn Cline

Cline and Shields unintentionally coordinated in another Tommy Hilfiger white button-down and the same plaid mini skirt. However, the Outer Banks star swapped Shields’ knee-highs for semi-sheer socks and loafers.

Shay Mitchell

The BÉIS Travel founder gave off major light academia vibes in an oversized sweater, Shields’ exact trench coat, and a layered pinstripe button-down. Similar to Harlow, she gave her final ‘fit an edgy flair with a baseball cap and chunky Chelsea boots overtop peek-a-boo socks.

Jenna Lyons

On Sept. 8, The Real Housewives Of New York alum was instantly recognizable in a champagne-colored suit set at the 3.1 Phillip Lim runway show. In true Lyons fashion, she accessorized her outfit with patent leather flats and square-shaped sunglasses.

Alanis Morissette

For her S/S ‘25 debut, the Grammy winner chose a two-tone jumpsuit in gray and army green, alongside a suede crossbody bag, and pointy pumps all from 3.1 Phillip Lim.

Victoria Monét

On Sept. 8, Monét solidified herself as one to watch this NYFW in a cutout-heavy LBD and slouchy thigh-high boots at the Off-White show.

Mary J. Blige

The Queen of R&B was also in attendance at the Off-White show. She went a more vibrant route than Monét in a criss-cross yellow bandeau top, a coordinating letterman jacket, and skintight boots.

Alessandra Ambrosio

Outside the Off-White show, Ambrosio was snapped by the paparazzi in a semi-sheer mini dress with lingerie-inspired lace embellishments and an of-the-moment hood.

Suni Lee & Camila Cabello

The Olympic gold medalist stopped for a photo op with Cabello ahead of the Off-White fashion show. Lee looked luxe in a gray mini dress while Cabello embraced the autumnal energy in a semi-sheer black turtleneck maxi dress.

Paris Jackson

Michael Jackson’s daughter proved her sartorial prowess in a button-down mini dress adorned with a blue and black checkered print.

Chloë Sevigny

Inside the launch of Myth Magazine on September 7, Sevigny exuded It-girl energy in a graphic T-shirt dress and platform UGG boots.

Rihanna

The room went silent at the Sept. 6 Alaïa show as Rihanna arrived in a rhinestone-embellished mesh shawl courtesy of the atelier alongside lace-up sandals from Amina Muaddi.

Hayley Williams

At the Susan Alexandra & Rachel Antonoff show on Sept. 6, the front woman of Paramore channeled the coquette aesthetic in a scalloped cardigan and mini skirt set. She added to the girly finish with transparent pastel pink tights, matching sky-high platforms, and a pearlescent handbag.

Martha Stewart

Before taking her seat next to Thom Browne (one of her go-to designers) at the Libertine show on Sept. 6, Stewart showcased her eccentric ensemble, starting with a timeless ascot, a floor-length coat, and wide-leg trousers. Her entire look was topped with a floral-inspired print.

Jasmine Tookes

Looking every bit a fashion muse, Tookes attended the Brandon Maxwell show on Sept. 6 in an all-black outfit. She accessorized with one of her tried-and-true handbags from Hermès.

Suni Lee

At the Brandon Maxwell show, the gymnast donned a floral-printed LBD from the label.

Tracee Ellis Ross

One of Willy Chavarria’s longest supporters, Ross nailed the capris trend with ease at the designer’s Sept. 6 spectacle. She brightened up her neutral white bottoms with a red puff-sleeve top and matching peep-toe mules.

Ciara

Ciara’s latest look outside the Willy Chavarria show featured contrasting patterns and a slew of menswear-inspired silhouettes, starting with ultra-wide-leg trousers and a floor-length blazer coat.

Lourdes Leon

Madonna’s daughter kept summer alive at the Willy Chavarria show in a micro-mini little red dress, chunky sneakers, and a Louis Vuitton denim-covered top-handle bag.

Joey King

King was one of the first A-listers to arrive at the Ralph Lauren show on Sept. 5. The Kissing Booth star styled a variety of sporty staples, including a vintage-esque letterman jacket, mid-wash jeans, and a black shoulder bag — all from Ralph Lauren.

Laura Dern

Dern doesn’t attend a ton of fashion week events, but you can always count on the Big Little Lies actor to serve a look for Ralph Lauren. She brought her stealth-wealth style to the front row in a navy blazer and pleated ivory trousers.

Dr. Jill Biden

Given Ralph Lauren is one of the First Lady’s go-to labels, it comes as no surprise that Dr. Biden was on the guest list in the Hamptons. She approved the brooch renaissance atop a fitted black pantsuit.

Naomi Watts

Before heading to the Toronto Interational Film Festival a few days later, Watts stopped at the Ralph Lauren show in a charcoal gray wrap dress and various dark brown accessories.

Emily Ratajkowski

Two days before NYFW began, Ratajkowski attended the Proenza Schouler S/S ‘25 show in a sleeveless black tank, a midi-length leather skirt, and chunky white boots. Extra points for her cherry red handbag.