Politics may have been the headline of the night, but Jewel Kilcher proved that timeless style never takes sides.
Standing 5 feet 5 inches tall, the Alaskan singer-songwriter—best known simply as Jewel—brought a touch of understated glamour to Comedy Central’s Roast of Rob Lowe in August 2016.
Jewel brings understated glamour to Comedy Central’s Roast of Rob Lowe, glowing in a plunging black keyhole dress and diamond-drop earrings on August 28, 2016, in Los Angeles (Credit: FayesVision / WENN)
What began as a comedic jab fest quickly became an unexpected cultural flashpoint when conservative commentator Ann Coulter, promoting her pro-Trump book In Trump We Trust, joined the panel.
Yet while the room buzzed with political tension, Jewel kept her calm—and her style—on point.
The singer-songwriter showcases her figure in a sleek black dress with a thigh-high slit, styled with lace-up Rupert Sanderson “Irma” pumps for an elegant edge
Wearing a plunging black keyhole dress that perfectly flattered her petite frame, Jewel grounded her look in timeless sophistication with black lace-up Rupert Sanderson “Irma” pumps—a refined choice that reflected both her effortless poise and the designer’s meticulous artistry.
Now headquartered in Fitzrovia, London, the brand remains a quiet powerhouse in luxury footwear, balancing artisanal Italian production with modern global reach—making Jewel’s choice of Sanderson heels not just fashionable, but enduringly refined.
A close-up of Jewel’s black satin Rupert Sanderson “Irma” pumps, featuring delicate ankle-wrap straps and pointed toes that elongate her 5′5″ frame
Nearly a decade later, her blend of elegance and confidence still feels refreshingly modern—a reminder that even in heated times, great shoes and good humor can outshine the drama.
Jewel adds humor to the night by posing with a heart-shaped Rob Lowe pillow, proving her playful personality matches her polished red-carpet style (Credit: Jewel’s Instagram)
Jewel threw a few punches. With a smile on her face and her guitar in hand, Jewel made a few humorous remarks about Coulter, but one in particular stood out.
She quipped, “Jeff Ross is going to party like it’s 1999, Ann Coulter is going to vote like it’s 1899,” while looking at Coulter.
She followed it up with, “Ann, you do look great though. You’re almost as slim as Donald Trump’s chances of winning the election, so that’s pretty impressive.” Ouch.
Rupert Sanderson’s Legacy of Timeless Glamour
As Jewel’s black lace-up “Irma” pumps reminded us, Rupert Sanderson’s designs embody the perfect balance of refinement and individuality.
His shoes have graced countless red carpets and stages, worn by women who appreciate craftsmanship as much as confidence.
Explore more unforgettable Rupert Sanderson moments below — each one a testament to the artistry behind this celebrated British label.
👠 Explore Rupert Sanderson’s Elegant Shoe Moments:
- 🌍 Rupert Sanderson: The Malaysian-Born British Shoe Designer Who Conquered Luxury Footwear — an in-depth brand spotlight exploring his refined design philosophy and global success.
- 🌸 Rupert Sanderson’s Dangerously Sexy Spring and Summer Collection — a look at his seasonal silhouettes, from sculptural heels to sleek satin pumps.
- 🎬 Astrid Bergès-Frisbey Stuns in Chanel Mini Dress and Rupert Sanderson “Zandy” Sandals — a red carpet pairing that embodies Parisian chic with modern minimalism.
- 🎤 Bebe Rexha Turns Heads in $700 Rupert Sanderson Heels and a Shimmering Gown — proving how statement heels elevate a bold, confident stage presence.
- 👗 Cate Blanchett’s Red Carpet Elegance in Rupert Sanderson “Barri” Sandals — an example of timeless style through subtle luxury and craftsmanship.
- ☀️ Lindsay Lohan Glows in “Tiffany” Sandals While Promoting UNOde50 Jewelry — a relaxed Mediterranean look featuring sleek Rupert Sanderson heels.