From Snakeskin Boots to Sculptural Heels: The Top Shoe Moments at the 2025 CFDA/Vogue Fashion Fund Dinner

Fashion’s biggest names and rising design talents gathered at The Crane Club in West Chelsea for the 2025 CFDA/Vogue Fashion Fund Dinner—an evening where personal style is celebrated just as enthusiastically as emerging American creativity. And this year, it was the footwear that quietly stole the spotlight.

Grand Prize winner Ashlynn Park of Ashlyn took home the $300,000 award for her sculptural, body-conscious womenswear—her second major CFDA honor in a week following her Emerging Designer of the Year win. Runner-up designers Stephanie Suberville of Heirlome and Julian Louie of Aubero each received $100,000, reinforcing the fund’s commitment to nurturing innovative, inclusive voices shaping the future of American fashion.

But while the awards highlighted the next generation of talent, the red carpet delivered unforgettable style moments of its own. From bold textures to razor-sharp silhouettes, the shoes worn by the night’s most photographed guests proved just how powerfully the right pair of heels—or boots—can define an entire look.

Vogue’s Anna Wintour, philanthropist Isha Ambani, designer Zac Posen, and Vogue’s Head of Editorial Content Chloe Malle hosted the event, welcoming an impeccably dressed crowd.

But three women emerged with particularly memorable shoe stories: Anna Wintour, whose snakeskin boots added unexpected edge to her signature polished style; Nina Dobrev, who paired her sculptural red Ashlyn gown with sleek black peep-toe mules; and Ciara, who elevated her dramatic Vaquera mini dress with glossy, razor-sharp d’Orsay pumps.

Anna Wintour, Nina Dobrev, and Ciara arrive at the 2025 CFDA/Vogue Fashion Fund Dinner, showcasing three distinct shoe stories—from Anna’s bold snakeskin boots to Nina’s sleek black peep-toe heels and Ciara’s glossy d’Orsay pumps on November 10, 2025, at the Crane Club in New York City (Credit: Elder Ordonez / INSTARimages)

Among the standout guests were Nina Dobrev, who turned heads in a striking red ensemble, and Ciara, who also made a statement in her signature black look, exuding confidence and sophistication as she arrived hand in hand with her husband, Russell Wilson.

Let’s take a closer look at what they wore.

Anna Wintour in Checkered Coat, Floral Dress, and Snakeskin Boots

Anna Wintour arrived in an outfit that looked polished, relaxed, and true to her signature style. She wore a gray checkered, double-breasted coat with padded shoulders, notched lapels, and beige-and-black buttons, giving it a classic, tailored finish. It seemed plain and simple from afar, but the structure and pattern made it feel commanding.

Under the coat, she wore a mint-green, sleeveless, floral maxi dress with a high neckline. Its soft color and print added a feminine contrast to the structured outer layer!

For accessories, Anna kept things minimal. She wore a Fendi shoulder bag encrusted with multicolored crystals and a statement gemstone necklace above the high collar of her dress. With her hands tucked into her coat’s pockets and her dark sunglasses on, she carried herself with quiet confidence.

Her minimal soft-pink makeup and her signature polished blonde bob added to the overall refinement, keeping the look clean, fresh, and put-together.

Anna Wintour looks cozy in her checkered coat and green floral dress, styled with a crystal Fendi bag and a pair of oversized sunglasses (Credit: Elder Ordonez / INSTARimages)

Anna Wintour’s Snakeskin Boots Add Texture and Edge

A pair of snakeskin boots, which brought a striking pattern to an already elaborate ensemble, completed Anna’s look.

While many would probably choose simple sandals or pumps, maybe something in silver or gold for a more cohesive, streamlined finish, I actually liked how the bold texture of the boots contrasted with the softer pastels and delicate florals. It added another layer of visual interest without feeling chaotic.

The boots had their own charm, injecting a bit of attitude and unexpected edge to the ensemble.

Anna Wintour grounds her print-heavy ensemble with beige-and-black snakeskin boots that add bold texture and edge (Credit: Elder Ordonez / INSTARimages)

Wintour’s snakeskin boots don’t just complete her outfit—they remind us why the print endures as a fashion editor favorite. Equal parts classic and rebellious, snakeskin has a way of elevating any look with depth, texture, and that unmistakable touch of edge. If her patterned boots have you in the mood for more reptile-inspired footwear moments, here are a few standout examples from across Your Next Shoes.

🐍 Snakeskin & Reptile-Print Footwear Moments

Nina Dobrev in Red Ashlyn Dress and Open-Toe Heels

Nina Dobrev was impossible to miss, as she donned a bold, sculptural red dress by Ashlyn, this year’s CFDA/Vogue Fashion Fund winner. It had a certain commanding presence, despite its understated silhouette. From the front, the sleeveless shape appeared clean and architectural, featuring a high, rounded neckline and a smooth, structured bodice that flowed seamlessly into a floor-length skirt.

The dress sculpted her frame. It was fitted at the waist, gently tracing her hips, then flaring into a skirt that moved fluidly.

What really caught my eye was the matching cropped knit bolero, almost like detachable sleeves, that she layered over the dress. It featured two black front buttons, which she left undone to give it an effortless, relaxed look. The cuff slits added a bit of edge, and when she later draped the bolero over her arms, it transformed into something that looked like sleek, opera gloves. It was a smart styling move that instantly made the entire look feel even more artful and dimensional.

Nina Dobrev stuns in a fiery red dress with a matching cropped, long-sleeved bolero from Ashlyn (Credit: Elder Ordonez / INSTARimages)

Minimalist Peep-Toe Heels Balance the Drama of Her Sculptural Gown

Nina kept her accessories simple to maintain a sophisticated look. She wore silver earrings, a few rings, and a cuff, all adding a cool metallic contrast against the fiery red of the dress. Her hair was worn straight and center-parted, tucked neatly behind her ears to keep the focus on the dress’s clean lines.

To finish, she carried a black Ahikoza Lilian Barrel clutch that matched her black high-heeled peep-toe mules.

Her shoes added a sleek finish to the look. They were simple at first glance, but the minimal silhouette worked beautifully against the drama of the red dress. I liked how the open toe softened the gown’s structure, giving the outfit a bit of lightness.

The heels added just enough lift to elongate her frame, and the contrast of black against all that red balanced the entire ensemble.

Nina Dobrev adds crisp contrast to her striking red dress with minimalist black peep-toe mules (Credit: Elder Ordonez / INSTARimages)

Nina’s red-hot Ashlyn moment is just one example of how consistently she delivers on the style front—especially when it comes to her shoe game. From sculptural heels to sleek boots, her footwear choices always add intention and polish to every look. If you’re in the mood to explore more of her standout style, here are a few curated Nina Dobrev shoe stories worth revisiting.

✨ More Nina Dobrev Shoe Moments

Ciara in Black Vaquera Dress and Black d’Orsay Pumps

Ciara looked ready for a night out, wearing an LBD that was anything but ordinary. Despite being all black, it easily commanded attention, and the volume alone gave it that “eyes on me” confidence.

She wore the $825 Vaquera Party Dress, crafted in the USA from ruched black taffeta. The material created, gathered, and crinkled gives the dress its exaggerated silhouette. The neckline plunged dramatically, dipping well below the sternum, while the oversized, sculpted sleeves ballooned out from the shoulder pads. It felt like the dress wrapped around her whole upper body in the most theatrical, fashion-forward way, and it was such a fun contrast to the simplicity of the rest of her styling.

The look finished with a fitted, ruched mini skirt that hit high on the thigh, its sleek silhouette perfectly counterbalancing the dramatic volume up top.

Ciara, with her husband Russell Wilson, looks party-ready in a ruched black taffeta mini dress with a plunging neckline and voluminous sculpted sleeves by Vaquera (Credit: Elder Ordonez / INSTARimages)

Shiny Black d’Orsay Pumps Elevate Ciara’s Dramatic All-Black Look

Ciara wore a few accessories so the dress could speak for itself. She wore just a couple of rings and a pair of statement stud earrings, providing just the right amount of sparkle. Her makeup remained neutral, featuring smoky eyeshadow and a deep, nude lip for a soft, seductive finish, while her hair was pulled back into a center-parted bun that complemented the outfit’s crisp lines.

What really pulled the whole look together were the sheer polka-dot tights, a subtle nod to retro glamour that played beautifully against the dress’s dramatic volume. And at 5’7½” (171.5 cm), Ciara made the most of the elongated lines created by her glossy black d’Orsay pumps. Sleek and razor-sharp, the heels featured pointed toes, thick ankle straps, and stiletto silhouettes that added structure, height, and a bold dose of attitude.

Their high-shine, almost lacquered finish brought striking contrast to the dress’s matte taffeta texture, giving her all-black ensemble even more dimension and polish.

Ciara steps out in sheer polka-dot tights paired with glossy black d’Orsay pumps featuring pointed toes and thick ankle straps (Credit: Elder Ordonez / INSTARimages)

To wrap up, here are a few curated celebrity shoe stories readers often enjoy exploring next — perfect if you’re in the mood for more standout heels, red-carpet footwear, and fashion-forward moments.

Explore More Celebrity Shoe Moments