Flashback: Ashley Benson Defines Red Carpet Elegance in Jimmy Choo Romy Pumps

During the 2018 Toronto International Film Festival at Toronto’s Winter Garden Theatre, Her Smell co-stars Cara Delevingne and Ashley Benson arrived separately on the red carpet, with Benson leaning into classic evening dressing in a fitted red Dolce & Gabbana dress and black Jimmy Choo pumps.

Rather than competing with the bold color of the sleeveless silk-blend dress, Benson kept the styling focused and minimal.

Her black suede Jimmy Choo ‘Romy’ heels added a sharp point-toe finish that balanced the clean lines of the dress while keeping the spotlight on the shoes and silhouette.

Ashley Benson keeps the focus on clean, body-skimming tailoring in a vivid red Dolce & Gabbana midi dress styled with soft waves and diamond drop earrings at the Her Smell premiere during the 2018 Toronto International Film Festival on September 9, 2018 (Credit: WENN / Ian Wilson / Regina Wagner / Future Image)

The American actress and model accessorized with Hearts On Fire earrings and completed her sultry look with black suede ‘Romy’ pumps by Jimmy Choo.

First introduced in 2016, Jimmy Choo’s pointed-toe ‘Romy’ pump has become one of the brand’s defining modern classics. Designed as a softer, more wearable evolution of Jimmy Choo’s earlier Abel and Anouk silhouettes, the Romy retains the label’s sleek stiletto shape while offering a slightly roomier toe box and a more balanced fit.

The style is known for its medium-cut vamp, which reveals just enough toe cleavage without feeling overly exposed, along with a centered stiletto heel that helps distribute weight more evenly than many ultra-steep pumps.

Compared to sharper styles like Christian Louboutin’s So Kate, the Romy is often considered easier to wear for longer events, making it a frequent choice for weddings, premieres, and red carpet appearances.

Ashley Benson rocking Jimmy Choo shoes at the premiere of Her Smell during the 2018 Toronto International Film Festival at the Winter Garden Theater in Toronto, Canada, on September 9, 2018 (Credit: WENN / Ian Wilson / Regina Wagner / Future Image)

The Romy comes in several heel heights, including the Romy Flat, the 60 mm kitten-style heel, the versatile 85 mm version, and the classic 100 mm stiletto. Materials range from patent leather and soft suede to the brand’s signature glitter finishes, including bridal favorites like “Platinum Ice” and “Viola Mix.”

While the Romy generally runs true to size, the Italian-made silhouette can feel narrow, particularly in patent leather and higher heel heights. Suede and kid leather versions tend to soften over time, and many wearers consider the Romy one of the more comfortable luxury pumps, thanks to its lightly padded insole and less-aggressive toe shape.

Jimmy Choo has since introduced the Love pump, a sharper, higher-vamp successor with more foot coverage, but the Romy remains the brand’s classic pointed-toe evening pump — polished, versatile, and easy to style with everything from tailoring to formal gowns.

Why the Jimmy Choo Romy Remains a Red Carpet Staple

With its sharp, pointed toe, clean silhouette, and range of heel heights, the Jimmy Choo Romy has stayed relevant over the years of red-carpet dressing without feeling tied to a single trend. Ashley Benson’s black suede pair worked as a quiet finishing touch to her Dolce & Gabbana dress at TIFF, showing how the style can ground a bold look without competing for attention.

From glitter-covered evening pumps to satin and suede versions worn by actresses, singers, and royalty, the Romy continues to appear in some of Jimmy Choo’s most recognizable celebrity fashion moments.