The 2026 WWD Style Awards shone as a glamorous highlight to kick off Golden Globes weekend, showcasing the very best in fashion, beauty, and style. But here’s where it gets controversial—what truly makes someone a style icon or trailblazer? Is it the awards, the celebrity attendance, or the stories behind the looks? Let’s dive into the night’s memorable moments and see what they reveal about the industry’s evolving standards.
Held at the elegant Regent Santa Monica hotel on Friday, the second annual WWD Style Awards gathered a star-studded lineup of luminaries, including legendary figures such as Demi Moore, George Clooney, Kristen Stewart, Cameron Diaz, Emily Blunt, Pamela Anderson, and many more prominent personalities. The event celebrated individuals who have made significant impacts across fashion, beauty, and style.
Among the top honorees, Demi Moore received the Fashion Icon award, while the legendary Giorgio Armani was posthumously recognized as the Red Carpet Visionary. Pamela Anderson was celebrated as a Beauty Icon, and Hailey Bieber took home the Style Trailblazer honor. Other recipients included Erin Walsh as Style Maker of the Year, Jason Bolden for Red Carpet Stylist of the Year, Adir Abergel for Red Carpet Hair Stylist, Lord Gavin McLeod-Valentine for Skin Savior, Kourtney Kardashian Barker as Wellness Entrepreneur, and Omega for Red Carpet Watch.
George Clooney, accepting Armani’s award on his behalf, remarked on the influence of the late designer. He joked, “If anyone should be speaking about Giorgio, it should probably be Richard Gere—since they truly made each other’s careers. But since Gere couldn’t be here, I’ll take the stand—f*ck him.” Clooney also expressed a poignant sentiment about Armani’s absence, emphasizing how much his legacy and industry presence are missed, especially noting Armani’s impressive 50-year career at just 91 years old.
In her heartfelt acceptance speech, Demi Moore humorously referenced her beloved dog Pilaf, who has become a fixture at her appearances. She teased, “I was told I missed my chance to take a photo with Pilaf and George. We’re actually working on a book—‘Pilaf and Her Leading Men’—so stay tuned.” Dressed in a glamorous Gucci gown styled by Brad Goreski, Moore reflected on her personal style, remarking that without guidance, she’d likely dress “like a 12-year-old boy.” Yet she valued the versatility of fashion as an avenue for storytelling and self-expression, emphasizing the fun and effort involved.
Pamela Anderson, speaking with her usual charm, acknowledged the unpredictable journey of her career, saying, “These past few years have been full of surprises. I never really know what’s next, but I’m okay with that. I want to work with everyone here—actually, I need some help over here!” Her infectious humor highlighted the camaraderie and playful spirit of the event.
Hailey Bieber underscored the importance of collaboration, praising the creative team behind every polished look—hair, makeup, styling—but was humorously interrupted by Anastasia Soare, who shouted “and eyebrows!” reflecting the legendary artist’s signature touch.
Kourtney Kardashian Barker kept her speech brisk but impactful, sharing a lesson she learned: “I was once told I didn’t understand what it takes to run a successful business I’m passionate about. Turns out, I do.” Her words resonated with anyone pursuing their dreams.
Jason Bolden, who rarely accepts awards, explained his focused approach, “I usually don’t give speeches or accept awards—I prefer to keep my head down and just do my work. But tonight, I want to thank everyone who has helped me get here—including my clients like Cynthia Erivo and Nicole Kidman—and encourage everyone to ‘pay attention, be conscious’ and remember the importance of kindness and progress.”
Cindy Crawford offered simple yet profound advice to those hesitant about experimenting with fashion. “When you’re a kid, you don’t care what others think when you dress up. Wear what makes you happy—fashion is about self-expression. Don’t overthink it.”
In terms of bold style statements, Chanel Iman made a striking appearance in a vibrant chartreuse feathered coat and mini-dress, embracing the new year with a daring fashion choice. She reflected on her unconventional look, saying, “I usually wouldn’t go for feathers and charms, but for the new year, I thought, why not?” Her playful attitude exemplifies the celebratory spirit of the night.
Iman also shared her excitement about longstanding collaborations and the recognition of her peers, especially Hailey Bieber’s recent accolades, emphasizing the importance of building genuine relationships in the industry.
Bieber herself joked about her online presence, noting, “My style is very documented—I can’t delete what’s on Google Images!” She shared her moments of genuine confidence when everything came together perfectly—from hair and makeup to wardrobe—making her feel her absolute best.
Celebrity makeup artist Patrick Ta lauded Bieber’s influence and projected future beauty trends, hinting at more colorful, bold shades making their way onto the scene. “While natural skin always reigns, expect bursts of color and playful shades to pop up soon,” he teased.
Reflecting on the broader industry, Marianna Hewitt from Summer Fridays celebrated the diversity of talent being honored and expressed her excitement about the renewed wave of creative freedom in fashion. “Last year brought many new designers and ideas—I love seeing fresh pieces and trends like animal print coming back as staples.”
Beauty pioneer Diana Madison highlighted Pamela Anderson’s role in shaping the minimalist movement, praising her for embracing natural beauty and encouraging others to do the same. “Pamela was one of the original trailblazers of the ‘less is more’ aesthetic—she owns her skin and her authenticity.”
Fashion veteran Rachel Zoe emphasized how style influences emotional well-being. “How you present yourself externally impacts how you feel inside—not superficially, but emotionally. Style is about expressing your true self.” She believes fashion’s purpose is personal, whether it’s dramatic or understated, emphasizing that trends are secondary to individual personality.
TV personality Christine Chiu welcomed the return of bolder, more colorful fashion, dismissing the quiet luxury trend in favor of louder, more expressive styles. “It’s exciting to see fashion embracing color and creativity once again,” she said.
And this is the part most people miss—understanding that these moments at award shows aren’t just about glamour; they reflect deeper shifts in how we see ourselves and express ourselves through fashion and beauty. What are your thoughts? Do you believe trends are merely superficial, or do they hold real cultural significance? Share your opinion in the comments below!
