In case you haven't noticed, our editor at large Gayle King is rarely seen in pants—let alone jeans. As she once told The Coveteur: "I very, very seldom wear pants. I wear dresses 99.9 percent of the time. I like them best."

But the CBS Mornings anchor recently made an exception when she interviewed Telfar Clemens, the Liberian-American designer behind the wildly popular Telfar Shopping Bag, which has been worn by Gabrielle Union, Congresswoman Alexandria Ocasio-Cortez, and even Oprah. "We are so excited about having the bag," she told Clemens when she selected it as one of her 2020 Things. "I appreciate the craftsmanship and the thought that went into making it so superior."

While visiting the 16-year-old brand's Brooklyn studio for a CBS segment, Gayle got a peek at what Clemens described as their "stuff-that's-coming-up" board, which includes dozens of sweatshirts, shoes, Shopping Bags, and other genderless designs. "People say that, and they're saying it as a buzzword. It's not just something you scroll online...it's actually like, you saw your mom in it, and you saw your brother in it," he said. "And it is OK. I don't know why people pressure themselves to be so stressed. Fashion doesn't have to be stressful. It can just be cool."

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One item in particular stood out to Gayle: the brand's "Thigh-Hole" jeans. "My eye goes to this—help me understand what this is," she said, pointing at the trendy design, which, as the name suggests, features cutout details at the thigh. She added, "And this is a hot-selling item?"

"This is the fastest-selling item in the new collection," Clemens replied.

Even after looking at a few of the brand's other upcoming pieces, including puffy winter jackets and a duffel bag that Gayle says is "going to give the [Shopping] Bag a run for its money," our our editor at large still found herself "worrying" about the trendy pair of jeans. In response, Telfar's creative director, Babak Radboy, told Gayle, "You've got to try it on."

"You're overthinking it," Clemens added. "We're going to do the Thigh Hole Challenge, and I'll show you how it's done."

Which is exactly what Clemens and Gayle did. "You look so good!" Clemens yelled when Gayle came out wearing the jeans with a white, off-the-shoulder top. "Look at how fab you are!"

But Gayle disagreed: "You know I look ridiculous!" said Gayle. "I just did this for the story—I will never wear these jeans."

She added, waving at the camera: "But to all of you...I salute you!"


preview for Real Women Try Out Wild Denim Trends
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Melissa Goldberg

Melissa is a former editor at Oprah Daily.