Inside the 2026 WWD Style Awards: Hollywood’s Most Fashion-Forward Night Before the Golden Globes
On the eve of the Golden Globes, the 2026 WWD Style Awards turned the Regent Santa Monica into a high-glamour runway, with Demi Moore, George Clooney, Kristen Stewart, Cameron Diaz, Hailey Bieber, and Pamela Anderson offering a snapshot of where Hollywood style is headed next. Blending old-school star power with Gen-Z cool, the second annual ceremony quietly cemented itself as fashion’s true Golden Globes pregame.
Inside the 2026 WWD Style Awards: Hollywood’s New Fashion Barometer
What used to be a quick photo-op stop on the way to Beverly Hills has become a fully fledged style summit. In just its second year, the WWD Style Awards have evolved into a red-carpet bellwether for awards-season trends, with stylists, designers, and A-listers treating the Regent Santa Monica like a testing ground for Golden Globes silhouettes, color stories, and risk levels.
With a guest list spanning Demi Moore’s ageless glamour, George Clooney’s timeless tailoring, Kristen Stewart’s androgynous edge, and Hailey Bieber’s influencer-era polish, 2026’s ceremony doubled as a live mood board for where celebrity fashion is going this year.
How the WWD Style Awards Became a Pre-Globes Power Player
Women’s Wear Daily has covered fashion’s inner workings for more than a century, but launching the WWD Style Awards signaled a shift: instead of just chronicling who wore what, the publication is now actively canonizing the celebrities and creatives shaping the visual language of Hollywood.
The second edition of the awards arrives at a time when the pre-show glamour economy is more influential than ever. Streaming fragmentation may have dented the cultural dominance of the Golden Globes themselves, but red-carpet visuals still travel everywhere at light speed—TikTok, Instagram, and fashion subreddits dissect each look in hours.
“The WWD Style Awards are about influence, not just elegance—who is actually moving the needle on how people dress in 2026.”
By anchoring its ceremony right before the Globes, WWD positions itself as the first major checkpoint of the season. A win or a viral look here can validate a stylist’s narrative before the more traditional awards even begin.
Demi, George, Kristen & Co.: The Night’s Quietly Radical Guest List
The magic of the 2026 WWD Style Awards isn’t just who attends, but what they collectively represent. This year’s lineup offered a cross-generational snapshot of Hollywood in flux—where legacy icons and disruptive dressers now stand side by side.
- Demi Moore continued her late-career fashion renaissance, leaning into architectural silhouettes and inky, camera-loving fabrics that telegraph control rather than nostalgia.
- George Clooney doubled down on his persona as Hollywood’s last classic movie star: immaculate suiting, unfussy grooming, and a cut that whispers “I know my tailor” more than “I know my stylist.”
- Kristen Stewart served her now-signature gender-fluid tailoring—sharp shoulders, softer lines, and a willingness to play with proportion that’s made her a staple in high-fashion campaigns.
- Cameron Diaz brought a relaxed, coastal polish that fits her new era of selective public appearances—less ingénue, more effortless insider.
- Hailey Bieber represented the influencer-luxury crossover, with a look calibrated for both the step-and-repeat and a billion-pixel zoom on Instagram Stories.
- Pamela Anderson, now firmly in her late-style icon era, leaned into clean, minimal choices that underline how far she’s moved from ’90s bombshell clichés.
That mix matters. It signals that “style” in 2026 is measured not just by youth or campaign relevance, but by narrative: who has evolved, who is experimenting, and whose clothes tell a longer story than a single season.
2026 Red Carpet Style Trends Previewed at the WWD Awards
While every celebrity had their own agenda, a handful of clear fashion trends emerged from the room—many of which are likely to reappear at the Golden Globes within 48 hours.
- Understated glamour over high-drama gowns
Maxi lengths and liquid fabrics were present, but over-the-top ballgowns were largely replaced by sleeker, column-like shapes that read well both in person and on small screens. - Midnight hues instead of high-wattage color
Deep navy, black, charcoal, and oxblood felt more modern than pure jewel tones, playing into a subtler, almost “stealth wealth” palette. - Gender-fluid tailoring as the new norm
Kristen Stewart wasn’t alone in blurring suit codes—relaxed fits, elongated jackets, and softer styling choices appeared on multiple guests of all genders. - Minimalist beauty, maximalist jewelry
Hair and skin stayed natural and glowy, clearing the stage for statement earrings, sculptural cuffs, and vintage-inspired cocktail rings to do the talking.
These choices track with a broader shift in celebrity style: the look has to survive high-res scrutiny and still feel wearable enough to spawn “get the look” content within hours.
Why the WWD Style Awards Matter for Stylists, Brands & Streaming Audiences
Beyond great photos, nights like this are quietly strategic. Stylists use the WWD Style Awards to test-drive bolder narratives—maybe a star known for princess gowns tries a sculptural suit, or a typically neutral dresser leans into color. If the internet approves, similar risks are more likely to reappear at higher-stakes shows.
Brands, especially luxury houses and emerging designers, treat the event as a soft launchpad. A dress that trends on social from Santa Monica can pick up demand in retail and resale channels long before awards-season campaigns end.
“It’s like an A/B test for the Globes,” one stylist joked on the sidelines. “If a risk works here, we know exactly how far we can push it on Sunday.”
For viewers, the WWD Style Awards slot neatly into the new rhythm of consumption. Instead of waiting for a single lavish telecast, fashion fans follow a rolling feed of look-by-look coverage across events. The Regent Santa Monica effectively becomes episode one of the unofficial “Awards Season Style” series.
Highlights, Weak Spots & The Looks We’ll Be Talking About
Not every fashion experiment landed, and that’s part of the appeal. The room felt less rigid than traditional awards galas, giving space for hits, near-misses, and conversation starters.
- Strongest looks: Demi Moore’s sculpted, almost armor-like eveningwear and Kristen Stewart’s nonchalant tailoring both felt like reference points we’ll see echoed through the season.
- Most on-brand: George Clooney’s unwavering commitment to classic menswear reminded everyone that evolution isn’t mandatory if your signature is already bulletproof.
- Underwhelming moments: A few ultra-safe, minimal gowns blurred into one another—polished but forgettable in a social media feed that’s increasingly crowded with bold editorial looks.
In editorial terms, that mix is a win. The WWD Style Awards are finding their footing as the place where fashion insiders can nerd out on fabric choice and fit, while casual fans simply enjoy the spectacle.
What This Means for the Golden Globes Red Carpet & Beyond
If the 2026 WWD Style Awards are any indication, expect a Golden Globes red carpet that leans into confident understatement: sharper lines, moodier palettes, and looks engineered for longevity on social more than shock value.
The biggest takeaway isn’t a single dress or suit—it’s the idea that pre-shows like this have become essential chapters in the fashion narrative. For celebrities, it’s a chance to stake out a season-long identity. For brands and stylists, it’s a live experiment. For viewers, it’s one more excuse to keep scrolling.
As the WWD Style Awards grow into their third and fourth editions, don’t be surprised if this Santa Monica stop becomes as scrutinized as any major awards ceremony. In a fragmented media landscape, the red carpet may be one of the last truly shared pop culture experiences we have—and nights like this prove it still has plenty of style stories left to tell.
