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Street Style - Day 4 - Milan Fashion Week Womenswear Fall/Winter 2023/2024

Source: Edward Berthelot / Getty

Some of our favorite, stylish celebrity women can rock almost anything, including menswear. Sabrina ElbaTeyana Taylor, and more have been seen at fashion shows and in these streets looking as dapper as guys in masculine threads. The girls’ style versions of menswear are epic, from full suits to Polo shirts. And they are out here slaying in their ensembles like nobody’s business.

Menswear offers various modish styles, giving women flexibility when it comes to their outfits. The macho attire provides a comfortable, oversized look that women have embraced, making it look fabulous. While it’s popular for the ladies to celebrate our silhouette with body-hugging dresses and form-fitting jeans, an occasional bulky sweater or loose-fitting pants looks just as fresh as a frilly frock – if styled correctly.

If you’re wondering which stars look chic in menswear or need tips on pulling your next menswear garb together, look no further than the ladies below. Here are five celebrity women who look swaggy in men’s clothing.

5 Celebrity Women Who Look Swaggy In Menswear  was originally published on

1. Sabrina Elba

Sabrina Elba Source:Getty

Sabrina Elba did no wrong in this full Gucci menswear look. The gorgeous model is known for flaunting her curves in ornate gowns, but this relaxed, fly outfit is one for the books. Elba even threw in a men’s tie, which poshly tied the look together.

2. Teyana Taylor

Teyana Taylor Source:Getty

Teyana Taylor and menswear are best friends. The artist has been donning menswear since she first stepped on the scene. Taylor looked clean as a whistle in this Thom Browne multi-print suit. Like Elba, she fabulously rocked a tie. And her dog-shaped bad was the perfect accessory to her men’s suit.

3. Rihanna

Rihanna Source:Getty

Rihanna’s usual style consists of pairing women’s and menswear looks that speak to her tomboy, feminine aura. In this recent photo, the Fenty CEO went for a total menswear look in a striped Polo shirt, baggy jeans, and Timberland boots. We could blame pregnancy on her comfy attire choice, but Rihanna isn’t new to sporting menswear clothing, she’s true to it. 

4. Gabrielle Union

When it comes to looks, Gabrielle Union has a plethora of them. She jumps from fancy to comfy all the time. While out during Paris Fashion Week, the actress slayed in this dapper menswear coat, jeans, and blazer. 

5. Savannah James

Savannah James is a stylista, and she does menswear like a pro. In this clip, her stylist dressed her in a white crop Maison Margiela blouse and men’s Double T pants that were offset by ankle-strap heels. Mixing men’s and women’s designer looks is familiar to James, and every time she does it, she serves.