Why Blake Lively’s 2016 Jonathan Simkhai Look Is Still a Masterclass in Maternity Shoe Styling

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While promoting Café Society in New York City on July 12, 2016, Blake Lively stepped out of the Greenwich Hotel in Tribeca wearing one of her most memorable maternity street-style looks.

Pregnant with her second child, the actress paired a custom Jonathan Simkhai dress with Sophia Webster’s crystal-heel “Rosalind” sandals, creating a shoe-led outfit that continues to stand out nearly a decade later.

The peach-toned midi dress was a custom version of a design from Jonathan Simkhai’s Pre-Fall 2016 collection. Crafted from richly textured embroidered fabric, it featured scalloped edges, geometric eyelet cutouts, ruffled detailing, and a defined waist that highlighted her baby bump while maintaining an airy summer feel.

The combination reflected what made many of Lively’s maternity looks so successful: a balance of softness and structure. Simkhai’s signature embroidery and architectural detailing gave the dress visual depth, while the minimalist sandals prevented the look from feeling overly ornate.

Blake Lively heading out of the Greenwich Hotel to promote "Cafe Society"Blake Lively heading out of the Greenwich Hotel to promote “Cafe Society” in New York City on July 12, 2016 (Credit: WENN / David Livingston / Avalon / Instar / PNP)

The styling remained carefully balanced throughout. Lively accessorized with stacked Anita Ko ear cuffs and diamond jewelry, while a Christian Louboutin Paloma Patch Tote introduced a playful contrast with colorful embroidered patches and signature red accents.

Surrounded by photographers, Blake Lively highlights her baby bump in a textured coral-toned dress, balancing the fitted silhouette with minimalist strappy heelsSurrounded by photographers, Blake Lively highlights her baby bump in a textured coral-toned dress, balancing the fitted silhouette with minimalist strappy heels

Loose blonde waves and a soft pink lip kept the overall look polished but approachable for a daytime press appearance.

From multiple angles, Blake Lively’s maternity street-style moment showcases how her sculptural dress and barely-there heels move effortlessly as she greets fans and exits the hotelFrom multiple angles, Blake Lively’s maternity street-style moment showcases how her sculptural dress and barely-there heels move effortlessly as she greets fans and exits the hotel

She opted for the Sophia Webster “Rosalind” sandals, a red-carpet staple known for its minimalist upper and maximalist heel.

Blake Lively steps confidently across New York pavement in barely-there nude sandals, their crystal-embellished stiletto heels catching the light with every strideBlake Lively steps confidently across New York pavement in barely-there nude sandals, their crystal-embellished stiletto heels catching the light with every stride

The Sophia Webster “Rosalind” sandals were already emerging as one of the designer’s signature styles. Crafted from nude leather, the design featured three delicate straps across the foot, a slim ankle strap, and a sculptural stiletto heel embellished with stacked crystal beads that caught the light from every angle.

💎 Explore Sophia Webster’s Iconic “Rosalind” Crystal-Heel Moments:

The barely-there upper allowed the jeweled heel to become the focal point of the shoe, delivering statement-making glamour without overwhelming the rest of the outfit. Versions of the design in metallic and crystal finishes became celebrity favorites, but Lively’s nude pair remains one of the style’s most recognizable appearances.

The choice also aligned with a recurring theme in Lively’s wardrobe: crystal-forward footwear. At 5’8½” and wearing a US size 9 shoe, she frequently gravitates toward high-impact heels that anchor an outfit, and the “Rosalind” perfectly complemented the architectural details of her Jonathan Simkhai dress while remaining practical enough for a day of walking New York’s cobblestone streets.

A closer rear-angle view highlights the delicate ankle straps and sculptural crystal heels that elevate Blake Lively’s minimalist sandals into a true statement finishA closer rear-angle view highlights the delicate ankle straps and sculptural crystal heels that elevate Blake Lively’s minimalist sandals into a true statement finish

The look remains a reference point in both maternity style and celebrity shoe history because it demonstrates how statement footwear can transform an outfit without dominating it.

The Jonathan Simkhai dress provided texture and structure, but the crystal-heel sandals supplied the element most fashion fans still remember. Appearances like this helped cement the Sophia Webster “Rosalind” as a cult-favorite design later worn by stars including Kerry Washington and Peyton List.

More Blake Lively Shoe Moments and the Crystal-Heel Sandal Trend

Blake Lively’s Café Society press-tour look is a perfect reminder of why her style moments have such lasting replay value: she consistently lets the footwear do the heavy lifting. If you want more shoe-led coverage—plus deeper context on Sophia Webster’s iconic crystal-heel “Rosalind” sandals—keep scrolling for a curated set of related reads from the YNS archives.

👠 Explore Blake Lively & Sophia Webster Shoe Highlights on Your Next Shoes: