Jenna Lyons Is Still A Fashion Superstar In Her 50s: The Best Looks

Jenna Lyons is one of fashion's most influential designers, best known for inspiring women to wear flamboyant designs and bold silhouettes. With age comes style, and that much is certainly true for Lyons in her 50s. It's safe to say the fashion designer has built a reputation for having a great style throughout her career, and as she has grown, her wardrobe has expanded to include more stylish pieces. In 2013, when Lyons was in her mid-40s, the New York Times crowned her "the woman who dresses America." However, since turning 50 in 2018, the fashion designer has continued to make headlines for being a serial fashion superstar. 

In an interview with Sheerluxe, the fashion designer described her style as eclectic. "At my core, I'm a real magpie — I love sequins, diamonds and glitter," she said. "Some of my favorite pieces include a J. Crew collection sequin jacket, a feather skirt, a Suzie Kondi cashmere sweater, some Comme des Garçons camo pants — and you can't beat a good pair of vintage Levi's," Lyons added, later revealing that she also loves a good bargain.

Despite stepping away from her 27-year career at fashion retailer J.Crew, where she last served as creative director and president until 2017, Lyons has continued to shine in fashion, including with her own style. From sheer blouses to tailored suits, Lyons' looks in her 50s have been absolutely show-stopping.

Having entered the new era of her 50s, Jenna Lyons attended the Ballet Fall Fashion Gala in New York in 2019 in a ruffled ensemble. The fashion designer posed wearing a trench-inspired dress featuring a ruffled hemline and a tie at the waist. The beige number boasted a buttoned neckline, giving her look a tailored finish. Under her dress, Lyons wore a peach, ruffled skirt. The tulle skirt gave a voluminous silhouette to the look, and the polka-dot detailing added a fun, energetic touch.

In 2021, Jenna Lyons was spotted wearing a daring ensemble at New York Fashion Week. In true Lyons style, the fashion designer was clad in a tailored suit, consisting of navy pants, a navy blazer, and a navy bralette. By donning this risqué look well before joining "The Real Housewives of New York," Lyons proved her bold personal style is timeless and that she was unlike other Bravo stars who have had completely unrecognizable transformations. She completed her tailored outfit with brown sunglasses and black heels that featured a crystal-encrusted ankle strap.

After making her reality TV debut, Jenna Lyons went to "The Real Housewives of New York City" Season 14 premiere in 2023 and proved florals never go out of style. She looked effortlessly fashionable as she posed on the red carpet in a pair of straight-leg jeans. But what made the look stand out was the pink, sheer tulle blouse and floral statement jacket that she wore on top. Lyons' unconventional style suggested she would bring her fashionable flair to the series, and arguably gave the show one of the most head-turning transformations in Bravo's "Real Housewives" history.

In 2023, Jenna Lyons was approaching 55. The fashion designer proved age can be separated from style when she arrived at the "No Hard Feelings" New York premiere wearing yet another daring ensemble. Lyons posed at the event wearing a sheer blouse made with a metallic, netted material. She topped the revealing shirt with a cropped black blazer that concealed her midriff. The delicate flare of her trousers directly contrasted the structured silhouette of her blazer and suggested her time at J.Crew had made her an expert at tailored fashion.

In 2024, Jenna Lyons posed on the red carpet at a 92NY event wearing a flamboyant ensemble that seamlessly combined retro aesthetics. While the fashion designer's vibrant red tights nodded to the lively mod-inspired trends that dominated the 1960s, her long leather coat added a 1970s Matrix-inspired feel to her outfit. Her glossy silver roots drew attention to the sheen of her sleek jacket and emphasized her signature, tailored approach to style. Lyons' bold tights, tucked into dramatic, pointy red heels, hinted that her fashion experiments are endless.

By 2025, Jenna Lyons had entered her late 50s, and she continued to embrace some of her boldest looks to date. At New York Fashion Week, she elevated yet another tailored jeans-and-shirt look with a pop of color and a statement silhouette. The fashion designer donned a lively, oversized red fur coat. The vibrant color made quite the statement, which she topped off with a pair of large sunglasses.

Jenna Lyons may be edging toward 60 in 2026, but her style shows no signs of slowing down. In fact, the fashion designer's outfits have hinted that she is becoming more experimental with age. On one occasion at New York Fashion Week in February 2026, she attended a Christian Cowan show wearing an extravagant, sequin-encrusted dress that featured an extremely daring, plunging neckline. Although her past fashion moments show she is unafraid to show some skin, Lyons added her signature tailored touch by topping her metallic maxi dress with an unbuttoned white shirt and a structured blazer.

Jenna Lyons must be the proud owner of a range of timeless pieces. When the fashion designer attended the YSE Beauty Xtreme Glow launch in March 2026, she paired her dark-wash jeans (straight-leg, of course), with a simple white shirt and a black tie. She finished her look with a leopard-print jacket, a print  that is a timeless and sophisticated fashion trend. With her hair styled casually, Lyons exuded effortless style, and her relaxed pose completed the look.