How Women Have Been Redefining Menswear for Generations
His. Hers. Ours.
There’s something quietly subversive about a woman in a man’s shirt — a classic yet bold look that captures timeless, gender-fluid style. It’s effortless fashion with attitude, confidence, and individuality; the kind of style that feels modern, versatile, and completely her own.
At Regent, we’ve always believed that great style isn’t about labels or categories, instead it's about craftsmanship, comfort, and character. A well-cut jacket, a crisp Oxford shirt, or a beautifully made hat can belong to anyone; it’s all about how you wear it. Our shelves might lean toward menswear, but you’ll often find women styling our pieces with an ease that proves the point: good design is universal.
Women Who Changed the Rules
And the truth is, this isn’t new. Women have been reimagining men’s clothing for decades. Katharine Hepburn made trousers a symbol of independence. Marilyn Monroe turned denim and bomber jackets into soft rebellion. Diane Keaton blurred the boundaries of tailoring, and we see it in film too — moments on screen and icons in culture showing that it’s not only stylish but liberating, revealing how borrowing from men’s wardrobes can unlock a whole new realm of expression and confidence. For example, the iconic scene in Pretty Woman, where Julia Roberts made an oversized white shirt look effortlessly sensual. All these women were rewriting the rules long before gender-neutral fashion became a talking point, simply one borrowed piece at a time.
The roots go back even further. Military and workwear styles: the bomber jacket, the trench coat, the sturdy denim overshirt, were originally designed for utility, but still defined by gender - made for the men permitted to fight and work at the time. But as women entered new roles throughout the 20th century, these pieces took on fresh meaning: symbols of practicality, power, and quiet rebellion. What began as necessity evolved into expression and started a legacy that still drives modern fashion today.
Fast-forward to now, and the story continues. Bella Hadid, Hailey Bieber, and Emma Corrin are redefining modern dressing with structured shoulders, slouchy shirts, and tailored trousers. It is styling that’s fluid, confident, and rooted in the same principles: dressing for yourself, not for others. Another prominent example is Ralph Lauren; a brand that’s long championed unisex elegance and continues to build collections that cross generations and genders alike.
Timeless Style at Regent
At Regent, we see that same timeless fluidity in our own collections. The Baracuta G9 Harrington Jacket and Walter Denim Jacket, for instance, are staples that transcend trends and categories. They’re designed to be worn, loved, and shared by everyone.
That sense of shared style is something Walter have built their brand around too, championing denim for its universality and attitude. As co-founder Danny explains:
“Walter’s love of denim comes from its broad appeal, speaking to the wearer’s attitude, not their age or gender. We create vintage-inspired pieces in beautiful existing and ‘found’ fabrics, in fits and shapes that can work a range of body shapes. Fashion-forward yet timeless classics, packed with considered details, and built to last.
As always with denim, trying on new and unfamiliar styles or brands is where the magic happens — falling in love with a piece you’d never before considered. That’s where Walter sits. Original and unexpected. Authentic and ambitious.”
It’s an ethos that mirrors Regent's - that real style has never been about following rules, but rather it's about curiosity, confidence, and exploration. Like Walter, we believe that clothes come alive in the hands of the wearer, as they gather meaning, memory, and character over time.
Lula, one of the Regent family, captures that effortlessly. Whether it’s a Fjällräven crossbody bag slung across a worn-in overshirt or a cord cap with a handmade patch, her look blends practicality and playfulness, proof that style is about attitude and self-expression, not rules. Regent’s roots echo this story too. Jason’s mother, pictured decades ago in tweed and a flat cap, wore her husband’s jackets with the same natural flair we see on the streets today. It’s a reminder that gender-neutral clothing isn’t a new phenomenon — it’s part of a long tradition of individuality, comfort, and confidence.
Accessories, too, can look good on anyone. A Regent scarf, a pair of heritage gloves, or some Fjällräven outerwear add warmth and character to any outfit. They are shared pieces that move seamlessly between wardrobes. We love seeing couples or friends come in and find items they both love - a jacket that’s as flattering on her as it is on him, a hat that changes energy depending on who wears it. At Regent, we believe clothing should tell a story, not fit into a box.
And for those who want something made entirely their own, our Ladies’ Bespoke service offers the best of both worlds: craftsmanship with character, tailored to the individual. Because true style isn’t about gender; it’s about confidence, comfort, and craft. It’s about that quiet satisfaction of wearing something that just feels right.
So, borrow it. Steal it. Share it. Call it yours.
Because at the end of the day, the best clothes aren’t defined by who they’re made for: they’re defined by who wears them well.
Curated by Becky Colyer and Jason Regent