Chic Winter Outfits for Women Over 50: 5 Celeb-Inspired Looks to Try

When temperatures drop, winter fashion doesn’t have to mean bundling up in bulky layers and sacrificing style. The right outfit combinations can keep you warm while making a statement — and who better to take inspiration from than some of the most fashionable celebrities? While they may not all be over 50, their winter looks offer plenty of ideas for women who want to stay chic, polished and confident in colder weather at any age. Let’s take a look at 5 of the best celeb-Inspired looks to try.

Chic Celeb-Inspired Winter Outfits

From the timeless elegance of bouclé knit to the drama of an oversized fur-trimmed coat, these celebrity-approved pairings prove that great style has no expiration date. Whether you prefer a sleek, modern look or something with a touch of classic glamour, these winter outfit combinations are effortlessly stylish and easy to recreate.

Bouclé Knit and Jeans 

Elsa Hosk’s bouclé knit and jeans combo is a timeless winter look with a modern twist. The textured jacket adds polish, while denim keeps it relaxed, and cowboy-inspired boots bring a stylish edge.

This outfit is chic, but also wearable. Opt for a structured bouclé jacket for a refined silhouette, pair it with well-fitted straight-leg jeans, and choose sleek leather or suede boots in neutral tones. A roll-neck sweater underneath adds warmth without bulk.

This effortless combination balances sophistication and comfort, making it the perfect winter go-to.

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Statement Coat and Leather Pants

Olivia Munn’s combination of a statement coat and leather pants is the perfect balance of sophistication and edge. The structured outerwear elevates the look, while the leather pants add a modern, polished feel. A classic knit turtleneck keeps it effortlessly chic.

This pairing is stylish and versatile. Leather pants, when chosen in a tailored fit and a refined finish (like matte or coated styles), act as a neutral foundation—just like your favorite trousers. Pair them with a long wool coat or trench in timeless color like camel, black, or navy for an elegant contrast. A soft knit turtleneck underneath keeps it classic and flattering.

This combination is a capsule wardrobe essential — chic, easy to style, and perfect for winter dressing without sacrificing comfort or sophistication.

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Tweed and Feathers 

Demi Moore turned heads at the Charles Finch and Chanel Pre-BAFTA Dinner in a striking Chanel ensemble that blended timeless elegance with bold glamour. Her black iridescent tweed jacket, adorned with a cascading gradient of feathers, was classic and statement-making. Paired with a sleek matching skirt and Chanel jewelry, the look embodied Parisian elegance.

This combination offers a chic way to embrace texture and drama without being over the top. A tailored tweed jacket in a neutral or deep jewel tone instantly adds polish. Feathered or textured details, whether on the hemline, sleeves, or accessories, add a touch of playful luxury. To balance the look, keep the rest of the outfit sleek with a fitted skirt or tailored trousers.

This pairing proves that statement pieces, when styled thoughtfully, can feel refined and fashion-forward at any age

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Oversize Fur and Sleek Silhouette 

Chloë Sevigny embraced winter elegance at the Sundance Film Festival in a dramatic Saint Laurent ensemble that balanced bold volume with sleek sophistication. Her oversized bomber jacket, trimmed with plush animal-free fur, stole the show, while a long knit turtleneck dress created a refined, streamlined silhouette. It was a look that was effortlessly chic, glamorous, and undeniably cool.

This combination is a perfect way to embrace statement outerwear without overwhelming the frame. The key is in the proportions – pair an oversized faux fur or shearling coat with a fitted base, such as a knit dress or tailored trousers, to keep the look polished. Opt for neutral tones or deep hues for timeless appeal, and finish with sleek boots or minimal accessories to maintain balance.

This is how to do winter style with drama and sophistication. 

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Blazer and Trousers

Drew Barrymore is no stranger to wearing pantsuits – she wears them often, and for good reason. A well-tailored suit is effortlessly polished, timeless, and adaptable to any occasion. Whether she’s hosting her talk show or making a public appearance, Drew consistently proves that coordinated sets are a chic and easy way to pull an outfit together.

What makes this particular look stand out is the mix of patterns and neutral tones. Instead of a perfectly matching suit, she pairs a plaid blazer with wide-leg trousers in a complementary beige shade. Plaid, especially in neutral tones, has classic appeal that adds structure and vintage charm. Meanwhile, solid-colored pants balance the pattern, keeping the outfit refined rather than overwhelming.

This combination is a perfect example of how to wear tailored pieces with ease. A plaid blazer instantly elevates any look, and pairing it with wide-leg or straight-leg trousers in a complementary color creates a modern, effortless feel.

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Are yo inspired by any of these celebrity winter outfits? Which one would you wear?

– Simona Shemer 

Photos: Red Carpet Fashion Awards, Elle, Vogue, Who What Wear 

You may like to read more of Simona’s celebrity style posts like 2024 Celebrity Style Review: Fashion Trends That Shaped the Year and The Best Red Carpet Fashion at the 2025 Golden Globes (and the Worst!).

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