Back in October 2019, Women’s Wear Daily brought together the fashion world’s brightest stars for its fourth annual WWD Honors, held at the InterContinental New York Barclay.
The event celebrated innovation, artistry, and influence across the industry—spotlighting legendary names whose work continues to shape modern style.
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Among the night’s standout attendees were Drew Barrymore, Olivia Palermo, Emmy Rossum, and Nicky Hilton, who turned the black carpet into a masterclass in personal style as they honored icons like Giorgio Armani, Stella McCartney, Pierpaolo Piccioli of Valentino, and Kim Jones of Dior Men.
Retro Chic: Drew Barrymore in Stella McCartney Iridescent Sandals and Emerald Green Dress
Drew Barrymore attended the event to support her friend Stella McCartney, who was presented with the Honor for Corporate Citizenship.
Actress Drew Barrymore supports honoree Stella McCartney at the 2019 WWD Honors held at the InterContinental New York Barclay in New York City on October 29, 2019 (Credit: Derrick Salters / Instar / WENN)
She was fittingly dressed in a retro emerald-green dress from the designer’s Fall/Winter 2019 collection. It’s covered in the brand’s signature horse prints and features pleated ruching on the bodice, puff-rolled sleeves, and an asymmetric hem.
The color looked great against her complexion, but the silhouette seemed unflattering. It would have looked better if she had made good use of the belt detail and tied it around her waist.
Drew Barrymore brings retro charm to the 2019 WWD Honors in an emerald-green Stella McCartney horse-print dress styled with iridescent heels
She wore her hair in loose curls and sported barely-there makeup. A member of the Barrymore family of actors, Drew furthered the ‘70s vibe of her look with rose-gold-tinted aviators, gold hoop earrings, and gold bangles.
The actress glows in rose-tinted aviators and minimal makeup, letting her soft waves and statement earrings complete the vintage-inspired look
The 44-year-old actress complemented her dress with a pair of Stella McCartney iridescent sandals that showed off her red pedicure.
Her holographic Stella McCartney sandals showcased a glossy red pedicure and added a playful shimmer to the rich green ensemble
Made of faux leather, these sandals feature open almond toes, wraparound ankle-ties, and about 4-inch heels.
Stella McCartney Iridescent Faux Leather Sandals, $450
Timeless Elegance: Emmy Rossum Honors Armani in Crystal-Embellished Heels
Emmy Rossum helped honor Giorgio Armani with the John B. Fairchild award, which was accepted on his behalf by his niece, Roberta Armani.
Emmy Rossum poses with Roberta Armani at the 2019 WWD Honors, looking polished in Giorgio Armani separates and black ankle-strap sandals
The 33-year-old actress opted for a sophisticated yet straightforward black-and-white two-piece look from the Italian luxury fashion house.
It included a white, see-through blouse with a tuxedo-style satin bib detail, paired with a feminine black skirt featuring a thigh-high slit.
The “Shameless” star channels timeless elegance in a crisp white blouse and thigh-slit black skirt that perfectly show off her crystal-embellished heels
She kept the look classy, with her hair up in a bun and her face minimally made up, wearing a swipe of pink lipstick and winged eyeliner.
Wearing her hair in a sleek topknot and bold winged liner, Rossum lets her minimalist Armani look take center stage
The Shameless actress accessorized with Yael Sonia earrings and a pair of classic black open-toe sandals. They feature dainty ankle straps and black crystal embellishments on the toe straps.
Her black crystal-adorned sandals added subtle sparkle and complemented her dark manicure for a refined monochrome finish
Regal Goth: Olivia Palermo’s Valentino Gown and Black Boots Command Attention
To show her support for Maison Valentino’s creative director, Pierpaolo Piccioli, who was presented with the first-ever WWD Honor for Women’s Wear Designer of the Year, Olivia Palermo wore a creation from the fashion house.
Olivia was majestic in a black gown with a regal silhouette, complete with colorful floral embroidery on the sleeves.
Olivia Palermo channels regal elegance in a black Valentino gown with floral-embroidered sleeves at the 2019 WWD Honors in New York City
She accessorized with layers of gold necklaces and a pair of horn-shaped earrings. Her Roger Vivier Barocco-embellished black clutch perfectly matched her dress. Her choice of shoes, however, didn’t seem to complement her outfit.
Instead of wearing dainty sandals, she opted for a pair of black boots, which added a gothic vibe to the look.
Her choice of sleek black pointed-toe boots lent the romantic Valentino gown a modern, gothic edge
Her sleek center-parted ponytail looked perfect, but we’re not a fan of her purple eye makeup.
Wearing her hair in a center-parted ponytail, Palermo highlighted her look with metallic purple eyeshadow and layered gold jewelry
The fashion influencer was joined on the black carpet by her husband, Johannes Huebl, who looked equally impressive in a pinstripe suit, crisp white shirt, and maroon tie.
The fashion influencer was joined by husband Johannes Huebl, who complemented her statement Valentino look in a sharp pinstripe suit
Classic Charm: Nicky Hilton’s Valentino LBD and Black Pumps Prove Less Is More
Also showing her support for Piccioli was socialite Nicky Hilton Rothschild.
Nicky wore a Valentino creation similar to Olivia’s. The LBD features an A-line silhouette, sequin-embellished bell sleeves, a center seam, and a straight hem that’s cut above the knees.
Nicky Hilton keeps her look classic in a black Valentino mini dress with sequin-embellished bell sleeves and matching accessories at the 2019 WWD Honors
The hotel heiress styled her blonde locks into a half-updo with a black bow and wore black liner with false eyelashes to accentuate her blue eyes.
The hotel heiress wears her blonde hair in a soft half-updo with defined lashes and peach-toned makeup that highlight her signature blue eyes
She completed her look with a sequined purse and a classic pair of black pumps.
She completed her elegant look with timeless black pointed-toe pumps that balanced the sparkle of her embellished dress
Runway Edge: Hilary Rhoda’s Stella McCartney Dress and Over-the-Knee Boots
Hilary Rhoda stands out in a deep wine-red Stella McCartney dress featuring recycled patchwork detailing at the 2019 WWD Honors
Hilary Rhoda was at the event to show support for Stella McCartney. Like Drew, she fittingly dressed in Stella McCartney, selecting an entire ensemble from the Fall 2019 collection.
The model accentuates her bold ensemble with red lipstick and softly tousled hair for a modern, confident finish
The 32-year-old model looked fresh off the runway in a wine-red midi dress featuring an embroidered patchwork of recycled fabrics, loose long sleeves, and a deep V-neckline.
Her chunky over-the-knee Stella McCartney boots grounded the look with height and edge, completing the runway-inspired statement
She paired it with a pair of over-the-knee boots with about 1.5-inch platforms and 4.5-inch chunky heels.
Stella McCartney Over-the-Knee Boots, $995
Explore More Red Carpet Shoe Highlights
Even years after the 2019 WWD Honors, celebrity footwear continues to define red carpet fashion—from bold platforms to minimalist stilettos that command attention. These recent Your Next Shoes features spotlight how today’s stars are reinventing classic heels for the modern era.
👠 Explore More Celebrity Shoe & Fashion Moments on Your Next Shoes:
- 📍 “9 Celebrities Rocking Bold Heels and Head-Turning Outfits on the 2025 BET Awards Red Carpet” — covers multiple star footwear moments with heel heights, shoe sizes and brands.
- 🎬 “Pumped Up: How Celebrities Redefined the Timeless Pump at the 2025 Golden Globes” — deep-dive into pump-and-heel choices at a major awards event.
- 👗 “Chanel Spring 2025: Must-See Celebrity Front-Row Looks… & Their Shoes” — links runway/fashion-week context to celebrity shoe styling.