Lindsay Lohan turned heads this weekend with her edgy look at the Gucci Cruise 2027 fashion show held in New York City’s Times Square on Saturday, May 16. The actress attended the event alongside her husband, Bader Shammas, with the pair coordinating in sleek black outfits, serving “power couple” on the red carpet. Across social media, fans have singled out Lohan’s look, praising the styling while drawing comparisons to Madonna.
Lindsay Lohan Rocks Leather Two-Piece At Gucci Fashion Show
“The Parent Trap” star arrived at the fashion show wearing a black leather two-piece from the house’s Fall 2026 collection.
With her blonde waves down, Lohan dropped jaws in what resembled a motorcycle jacket partially unzipped to create a plunging neckline, paired with a matching zipper skirt with a slit that showcased her bare thigh.
She finished the look with a black bag, matching pointed-toe pumps, gold jewelry, and shield sunglasses.
Shammas, on the other hand, coordinated perfectly beside her in a tailored black suit layered over a matching black shirt with polished dress shoes, keeping the couple’s aesthetic monochromatic.
Fans Say The Look Is ‘Very Madonna’
Hours after the event, Lindsay Lohan shared clips of the outfit on Instagram, earning hundreds of compliments from admirers. Over on X, fans had already flooded the platform with photos and video clips that didn’t make it to Lohan’s feed.
Across platforms, many users agreed the look felt “very Madonna.” The combination of edgy styling, a confident attitude, and, of course, blonde hair evoked Madonna’s classic, rebellious, and glamorous image.
A few compared the styling to Charli XCX’s aesthetic, while some longtime fans used the moment to beg Lohan to release new music again. A smaller group admitted they still missed her iconic red hair era, but the overwhelming consensus was that she looked incredible.
Several commenters also reflected on how happy they are to see Lohan thriving again after the turbulent years that once dominated headlines surrounding her personal life.
Lindsay Lohan Also Stunned At Disney Upfront 2026
The Gucci appearance came shortly after another major fashion moment for Lohan at Disney Upfront 2026 in New York City. For that event, she wore a strapless couture gown from Ashi Studio’s Fall/Winter 2025 collection styled by Andrew Mukamal.
The gold beaded gown featured intricate embroidery, a sculpted black bra element along the sweetheart neckline, a corseted lace-up back that cinched her waist beautifully, and a trailing train to enhance the dramatic effect as she moved along the red carpet.
The fitted silhouette accentuated her figure while maintaining an air of elegance. Lohan kept the styling relatively minimal, with soft-glam makeup, loose blonde waves, and understated jewelry, allowing the gown itself to remain the focus. Black pumps elevated her frame for a final composed look that fans described as “absolutely stunning.”
She’s So Pretty In Green
This month, Lindsay Lohan also turned heads in an Oscar de la Renta Pre-Fall 2026 silk chiffon gown in a rich olive green shade. The flowing dress offered a soft, ethereal quality with its lightweight fabric and graceful drape, in sharp contrast to the more recent, edgier leather Gucci ensemble.
Fans were just as obsessed. Under her Instagram upload, one admirer gushed, “You look gorgeous,” while another dramatically declared, “In my book? The most beautiful woman on the planet!”
Lindsay Lohan Stars In ‘Count My Lies’
Beyond the red carpet, Lohan advances her acting career with a key role in the upcoming Hulu limited series, “Count My Lies,” marking her first leading role in a television series. The thriller, adapted from Sophie Stava’s novel, also features Shailene Woodley and Kit Harington.
Although the series is still in production, fan accounts have already begun circulating behind-the-scenes photos online as excitement continues building for the official launch.