Debbie Gibson brought retro polish and pop icon poise to Jimmy Fallon’s stage—pinstripes, red soles, and a smile that still knows how to headline.
Debbie Gibson has always known how to make an entrance. On September 8, 2025, the pop legend and Broadway alum appeared on The Tonight Show Starring Jimmy Fallon , reminding everyone that timeless style isn’t just about what you wear—it’s how you wear it.
Seated in a midnight-blue armchair with the New York skyline twinkling behind her, Gibson looked every bit the seasoned star. Her outfit? A masterclass in monochrome drama with a twist of rock-and-roll edge.
She wore a sleek black ensemble layered under a black-and-white striped jacket—structured, tailored, and just theatrical enough to nod to her stage roots. The stripes added movement and visual rhythm, echoing the musicality that’s defined her career. The silhouette was sharp but wearable, with clean lines that flattered without fuss.
Black high heels with signature red soles (hello, Louboutin?) peeked out as she crossed her legs—classic, confident, and unmistakably luxe. Jewelry was kept minimal, letting the jacket’s bold pattern and her radiant smile do the talking. The synergy between outfit and attitude was seamless: Gibson didn’t dress to impress, she dressed to express.
Debbie Gibson’s Tonight Show appearance was a reminder that style, like music, is about rhythm, confidence, and knowing when to hit the high note. For more moments that blend legacy with modern flair, explore our archive of celebrity style .
Naomi Scott brought structured elegance and editorial edge to Deadline’s TIFF studio—oversized tailoring, noir minimalism, and a pose that said: leading lady, no question.
Naomi Scott doesn’t need a red carpet to command attention. At the Deadline Studio during the 2025 Toronto International Film Festival, she turned a plain white backdrop into a fashion moment—proof that presence, not props, makes the picture.
In a sea of TIFF glitz and cinematic buzz, Scott’s look was a quiet rebellion: all-black, all-attitude, and all about silhouette. It was the kind of outfit that doesn’t beg for headlines—it earns them.
She wore an oversized black button-up shirt with voluminous sleeves, paired with high-waisted black trousers that elongated her frame and sharpened the silhouette. A large black tie anchored the look, adding a masculine edge that felt more Comme des Garçons than corporate. The fabrics were matte, structured, and deliberate—no gloss, no fuss. It was tailoring as armor, and Scott wore it like a shield of cool.
No jewelry, no embellishment—just black high heels with a clean finish, letting the outfit’s geometry do the talking. The synergy was stark and striking: every piece served the same purpose, to amplify Scott’s quiet intensity. Her pose—one hand on the hip, the other relaxed—was confident without being performative.
Fresh off her U.S. Open victory, Aryna Sabalenka brought trophy-worthy elegance to Jimmy Fallon’s stage—pleats, emerald tones, and a smile that could light up Flushing Meadows.
Aryna Sabalenka knows how to serve—on court and on camera. Just days after clinching the U.S. Open Women’s Singles title, the Belarusian tennis powerhouse graced The Tonight Show Starring Jimmy Fallon on September 8, 2025, with a look that was equal parts athletic triumph and red carpet finesse.
She didn’t just walk onto the stage—she arrived with a silver trophy nearly as radiant as her grin. The moment was celebratory, yes, but also symbolic: Sabalenka stepping into pop culture’s mainstream with the same force she brings to the baseline.
Her sleeveless, form-fitting green dress was a masterclass in understated glamour. The fabric hugged her frame with precision, while the pleated hem added movement and texture—like a nod to the rhythm of her game. The emerald hue was a clever choice: regal, refreshing, and just bold enough to pop against the Tonight Show’s iconic blue backdrop. It was a silhouette that said “champion,” but whispered “style icon.”
Black high-heeled shoes grounded the look with a classic touch, letting the dress take center stage. Jewelry was minimal—no need for sparkle when you’re holding a trophy that gleams on its own. The synergy between her outfit and her achievement was seamless: nothing felt overdone, everything felt earned.
Aryna Sabalenka’s Tonight Show appearance was more than a media stop—it was a fashion statement wrapped in a sports milestone. For more moments where athletic excellence meets style elevation, explore our archive of celebrity photos .
