7 fashion-forward women that are menswear icons

Dad shirts and boyfriend jeans are a part of the urban sartorial dictionary, but fashion’s finest have been borrowing from the boys since Diane Keaton’s tailored waistcoats in Annie Hall and Princess Diana’s ’90s uniform of trim blazers over sweats. Today, style arbiters like Kendall Jenner and Hailey Bieber are following suit (no pun intended) by championing a masculine mood by celebrating the enduring power of a tailored blazer and pleat-front trousers. From work hours to after hours, sharp tailoring conveys power and poise, and Gen Z tastemakers pull off menswear better than the men themselves.
Ladies, take inspiration. Men, take notes – these 7 power players will teach you a thing or two.

Rihanna

We stan Rihanna’s I-accidentally-on-purpose-forgot-my-pants-at-home look. She dials up the borrowed-from-the-boys vibe with a baseball cap that lends an off-duty appeal. The slouchy shoulders, capacious sleeves, and unrestrained silhouette is stylishly subverted with ladylike pumps, a hint of lace, a neck mess, and a brazen red lip. Toting her signature mini Goyard purse, the look semaphores self-confidence and ease.

Emily Ratajkowski

Boxy blazers and pleated trousers are mainstays in Ratajkowski’s repertoire – they are endlessly versatile, as repeatedly paraded by the powerhouse. Ratajkowski downplays the severity of structure with a midriff-baring bralette, baseball cap, and box-fresh sneakers for an androgynous-meets-active turn. Gold jewellery offsets the look, while the ’90s streamlined sunnies lend the perfect finishing touch to the precision-cut tailoring.

Kendall Jenner

From wearing a waistcoat as a top to styling a classic white shirt in novel combinations, Jenner has BME – big masculine energy. She gives us a masterclass in effortless layering by invigorating wardrobe go-to's. The well-cut billowing shirt thrown over a basic Tee and khaki pleated trousers are straight from The Row’s S/S 2021 runway – you don’t have to be a minimalist to appreciate the clean staples and the artful layering. Jenner masterfully tempers the volume with barely-there strappy sandals.

Hailey Beiber

Hailey Bieber removes any seasonal association that comes with a blazer, giving the foundational wardrobe classic a summer spin by wearing it sans bottoms. She opts for an enveloping double-breasted blazer, complementing the clean-cut silhouette with experimental touches. The bucket hat takes the tailored blazer in a laidback direction, while the oft-hated socks and fuzzy slipper combination take this look from conventional to exceptional. The Prada Nylon is a cool-girl nod to the aughts.

Mary-Kate Olsen

When it comes to well-constructed and exquisitely tailored separates, the Olsen twins remain unrivalled. Mary-Kate embraces a tailored mood with a crisp slim-fitted white shirt buttoned up to her chin. She plays up its masculine connotation with black tailored trousers in a straight fit. The clean lines and simplicity of this classic combination carry an air of authority. The Olsen twins are purveyors of minimalism, putting an effortlessly chic spin on sharp cuts and trim silhouettes – their label The Row is an apt reflection of it.

Bella Hadid

Voluminous shapes with laidback nonchalance have Hadid’s stamp of approval. The billowy trousers, oversized blue-and-white-striped formal shirt, and chunky loafers are a subtle nod to utilitarian style goes preppy. Accompanying the relaxed silhouette is an assortment of mismatched accessories – a headband, a beachy necklace, ’90s slimline glasses, and a quilted Chanel handbag. The look is as practical as ever, but with a hit of cool.

Kaia Gerber

Look beyond biker jackets to a well-cut leather blazer. Kaia Gerber’s sharp jacket has an everyday sensibility that exudes effortless wearability. Offset its rugged appeal by shrugging it over something indisputably cool – a striped Tee and precisely tailored tapered trousers. Leather, on the other hand, makes the tailoring approachable. Gerber’s model-off-duty style is city-chic – loafers, noughties-inspired sleek sunnies, and a baguette tucked under her arm.

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