The second annual WWD Style Awards kicked off Golden Globes weekend on Friday at the Regent Santa Monica hotel. 

Guests included Demi Moore, George Clooney, Kristen Stewart, Cameron Diaz, Emily Blunt, Pamela Anderson, Mindy Kaling, Hailey Bieber, Kourtney Kardashian Barker, Cindy Crawford, Paris Hilton, Carolyn Murphy, Tyriq Withers, Jackie Tohn, Lisa Rinna, McKenna Grace, Chrishell Stause, Salem Mitchell, Skai Jackson, Chloe Cherry, Lauren Wasser and more.

The night’s honorees were Demi Moore for Fashion Icon; the late Giorgio Armani for Red Carpet Visionary; Pamela Anderson for Beauty Icon; Hailey Bieber for Style Trailblazer; Erin Walsh for Style Maker of the Year; Jason Bolden for Red Carpet Stylist of the Year; Adir Abergel for Red Carpet Hair Stylist of the Year; Lord Gavin McLeod-Valentine for Red Carpet Skin Savior of the Year; Kourtney Kardashian Barker for Wellness Entrepreneur of the Year, and Omega for Red Carpet Watch of the Year.

Clooney accepted the award on behalf of the late Giorgio Armani. 

“I would argue that if anyone should be up here talking about Giorgio, it should probably be Richard Gere. I think the two of them put each other on the map,” Clooney told the room. “But since he couldn’t show up and f–k him.”

Of Armani, Clooney added that his absence was felt in the room. “It’s an odd thing to say that he was 91 years old and he left us far too soon,” he said. “He just celebrated 50 years in the industry.” 

“I’m sorry I didn’t bring Pilaf tonight,” Moore said during her acceptance, referencing her dog, who has become a star in her own right thanks to many an appearance out and about with Moore. “I was informed that I was missing my chance to get a picture with her and George. We’re working on a book that is Pilaf and her leading men.”

Moore, who wore a Gucci gown styled by longtime stylist Brad Goreski, told the room that left to her own devices, she would dress “like a 12-year-old boy.” 

“But I also realized that these are also versions of me. That’s part of the beauty of the red carpet is I get to play,” she said. “It’s a place to express, to tell stories in a different way. And I’m really so grateful that I get to explore and that I’m entrusted to do so because it’s a lot of work, as any of you ladies will attest. A lot of work goes into it. And the most important thing is that I get to make it a lot of fun.”

“Who would have thought I’d be here?” Anderson told the room. “This has been such a wild couple of years full of surprises, and I always say I never know what’s next and I’m okay with that, which is kind of a practice. And so I’m just so proud of everybody here. I really kind of want to work with everybody here. I need some help over here. Anyway, I’m just winging it.”

“I know that everybody in this room would agree that we could never create the moments that we create without our amazing collaborators, from hair to makeup to styling,” Bieber said, before she was interrupted by the legendary eyebrow artist – and close friend – Anastasia Soare, who shouted “and eyebrows!” 

Kardashian Barker kept her speech short and to the point. 

“I was once told that I don’t know what it takes to run a business that I’m passionate about. Turns out I do,” she said. 

Bolden said he usually doesn’t accept awards and give speeches, preferring to keep horse blinders on and “don’t look left, don’t look right. Just look forward, do your job, head down. So I want to not make this about me, but make this about people that allow me to go on this journey and knock down doors for me,” he added, listing clients like Cynthia Erivo, Nicole Kidman, Michael B. Jordan and Withers, who attended the event with him.

Bolden also called on the room to “pay attention. Be conscious, be conscious, because we have to be kind and be considerate and also turn the page.”

Crawford had a simple message for anyone afraid to take risks with fashion.

“When you’re a little kid and you play dress up, you don’t care what other people think,” she said. “You’re doing it for yourself. So, I think just encouraging people — if they like it, wear it. Don’t be too worried. It’s not that serious.”

Standing out on the carpet, Chanel Iman stepped out in a chartreuse-green feathered coat and minidress, embracing a bold style moment for the new year.

“I normally wouldn’t go for something with feathers and charms and things, but this is a new year, new me, and I said, why not?” she said of the look.

That spirit of celebration carried over as Iman reflected on longtime collaborations, sharing her excitement about seeing Bieber honored for her achievements.

“We’ve worked together for many years, and it’s always nice to see people you’ve built relationships with get such incredible awards,” she said.

Asked about her own style evolution, Bieber remarked that much of it lives online.

“Mine is really well documented, you know? Can’t delete off Google Images, unfortunately,” she laughed.

Her standout moments are where she’s walked away feeling confident and proud of how everything came together.

“I definitely have had a few moments where I felt like everything worked together the way it was supposed to — the hair, the makeup, the lighting, the outfit,” Bieber went on. “Because I think sometimes what happens is when you’re at home and you do all the things, you’re like, ‘Wow, I look really good.’ And then you see the photos and you’re like, ‘Oh. I don’t know what happened there. But I felt really good when I walked out the door.’ So when it all works together, I think you walk away feeling great.”

Celebrity makeup artist Patrick Ta, too, praised Bieber’s influence across both fashion and beauty.

“I’m obsessed with Hailey Bieber. She’s a force to be reckoned with,” Ta said.

While glowing skin remains timeless, he hinted that a more playful beauty era is on the horizon.

“Skin is always in, but you’re going to see bursts of color, brighter, more bold shades,” he said of his next release.

Celebrating the night’s honorees as a whole, Marianna Hewitt of Summer Fridays highlighted the wide range of talent being recognized.

“There are so many people in front of and behind the camera that really make Hollywood what it is, and it’s amazing to be able to honor them,” she said.

Looking ahead, Hewitt said she’s energized by fashion’s renewed creativity and the personal expression emerging this season.

“Last year there were so many new creative directors, and now it’s exciting to see everything come to life,” she said. “I’m always refreshing to see what pieces I can add, shoes, jackets, bags. Animal print is a neutral for me.”

Beauty nostalgia was front and center for beauty founder Diana Madison, who praised Anderson as a trailblazer of the minimalist movement.

“Pamela Anderson singlehandedly started this minimal, no-makeup trend. She’s at the forefront of owning your skin and your beauty,” Madison said.

Reflecting on fashion more broadly, Rachel Zoe spoke about the emotional power of style and why glamour still matters, even in an industry she describes as challenging.

“How you look on the outside very much affects how you feel on the inside, not in a superficial way, but in a very emotional way,” Zoe said.

Rather than chasing trends, she added, fashion is ultimately about individuality, whether that means maximalist drama or pared-back simplicity.

“I don’t think of fashion in terms of trends but in terms of the person wearing it,” she said. “I love the return of drama and corsetry, but I also love that late-’90s simplicity from the Kate Moss era.”

That return to bold expression was welcomed by TV personality Christine Chiu, who sees fashion entering a more colorful, creative chapter.

“I’m happy that the quiet luxury era is quietly ushering itself away, and we can enjoy louder, more colorful creativity again,” she said.