When Cara Santana attended the W Las Vegas preview in Los Angeles on November 2, 2016, she provided a clear template for styling over-the-knee suede.

By pairing a ’60s-inspired Armani fringe dress with gray Stuart Weitzman “Highland” boots, she tapped into a retro-mod mood while spotlighting one of the most defining over-the-knee silhouettes of the 2010s.
Known for its second-skin stretch suede, signature tie-back detail, and leg-lengthening 95mm block heel, the Highland balances polish with practicality—delivering that coveted, “legging-like” fit that stays perfectly in place. The result feels both era-specific and enduring, a sleek transitional formula that continues to anchor fall styling years later.

The Highland’s staying power is just as evident in how widely it’s been embraced across the celebrity style spectrum.
Jessica Alba sharpened the silhouette with a lace minidress for a polished, red-carpet-ready take, while Paris Hilton leaned into its leg-lengthening drama with a festive mini and over-the-knee boots. Hailee Steinfeld gave the boots a jet-set spin with a streamlined shirtdress at Narita Airport, and Padma Lakshmi proved their versatility during a press tour, styling them with understated, pull-together separates.
From Olivia Palermo’s polished Paris Fashion Week layering to Cara Santana’s off-duty coffee runs, the Highland consistently adapts—shifting effortlessly between high-glam and everyday wear while maintaining its signature, leg-sculpting impact.

For the 5ft 4 (162.6 cm) actress, the thigh-high silhouette serves a functional purpose, creating a continuous vertical line that elongates her petite frame.

Santana’s frequent use of these boots across different environments—from red carpets to casual outings—highlights the versatility of the Highland’s four-inch block heel and stretch-suede construction.
She kept the rest of her look simple, skipping the jewelry—except for her engagement ring. Her messy bun and soft makeup rounded out her look.

While the original Stuart Weitzman “Highland” boots are now largely sold out, you can still shop the latest over-the-knee styles from the American footwear designer at Nordstrom and Zappos, where updated versions continue to deliver the same leg-lengthening silhouette and signature stretch fit that made the Highland a cult favorite.
From red-carpet glam to off-duty coffee runs, Cara Santana has proven she knows how to make a statement with her footwear choices. For more of her standout shoe and fashion moments, explore our curated features below:
More Cara Santana Shoe & Fashion Moments
👢 Cara Santana Shoe & Fashion Features on Your Next Shoes:
- 📸 Cara Santana Rocks Stuart Weitzman’s Highland Boots — A chic coffee-run look in West Hollywood, featuring the iconic Highland thigh-high boots.
- ✨ No Relation to Carlos, But Cara Santana’s Style Speaks … — A standout street-style moment: Cara in over-the-knee boots and a sheer top while leaving The Nice Guy in 2015.
- 🌟 Cara Santana Dazzles in Backless Tadashi Shoji and Embellished Schutz Sandals at the 2017 Golden Globes After-Party — Glam evening footwear spotlight.
- 👡 Cara Santana’s Cool-Chic Look: Loeffler Randall Lace-Up Sandals Steal the Spotlight — Casual-chic arrival look featuring lace-up espadrille sandals.