Borrowing from the boys
"beautifully made and often improve with age"
R — The idea of women borrowing from menswear is hardly new. Why do you think certain menswear pieces continue to feel relevant, even as fashion changes around them?
W.O. — I think the pieces that endure are rooted in timeless design rather than trends. They’re comfortable, functional, beautifully made and often improve with age. There’s a certain quiet confidence in menswear that has always appealed to me.
What I love most, though, is the conversation that happens when those pieces are worn by women. A perfectly tailored blazer, an oversized coat or a crisp cotton shirt can suddenly feel soft, elegant and unexpected when paired with something more feminine. That balance between structure and softness is something I find endlessly interesting.
W.O. — I think the pieces that endure are rooted in timeless design rather than trends. They’re comfortable, functional, beautifully made and often improve with age. There’s a certain quiet confidence in menswear that has always appealed to me.
What I love most, though, is the conversation that happens when those pieces are worn by women. A perfectly tailored blazer, an oversized coat or a crisp cotton shirt can suddenly feel soft, elegant and unexpected when paired with something more feminine. That balance between structure and softness is something I find endlessly interesting.
R — When styling women in traditionally masculine garments, what separates a look that feels intentional from one that simply feels oversized?
W.O. — Proportion is everything.
An oversized piece should never be the entire story, it needs something refined to ground it. A beautifully fitting tank, a lightweight cashmere sweater, a perfectly cut T-shirt or a trouser with the right rise creates the balance that allows the oversized piece to feel effortless rather than overwhelming.
Those foundational pieces are often the hardest to find, which is why they’re usually the first things I replace after a closet edit. They’re quiet, but they’re doing all the work.
Tailoring is equally important. A great tailor shouldn’t change the character of a garment, they should simply make it belong to the person wearing it. The goal is always for the woman to wear the clothes, never the other way around.
W.O. — Proportion is everything.
An oversized piece should never be the entire story, it needs something refined to ground it. A beautifully fitting tank, a lightweight cashmere sweater, a perfectly cut T-shirt or a trouser with the right rise creates the balance that allows the oversized piece to feel effortless rather than overwhelming.
Those foundational pieces are often the hardest to find, which is why they’re usually the first things I replace after a closet edit. They’re quiet, but they’re doing all the work.
Tailoring is equally important. A great tailor shouldn’t change the character of a garment, they should simply make it belong to the person wearing it. The goal is always for the woman to wear the clothes, never the other way around.
"I think great design is rarely confined by gender"
R — Are there particular menswear pieces you find yourself returning to time and again? What makes them so enduring?
W.O. — I’ve been searching for the perfect field jacket for years.
Whether it’s a true menswear piece or simply inspired by one, I still haven’t found the one. Because of my height and proportions, many of the men’s versions require so many alterations that they lose the ease that attracted me to them in the first place. So, for now, the search continues. (If anyone has recommendations, I’d happily take them.)
I also still think about a charcoal cashmere-cotton sweater from The Elder Statesman that somehow disappeared from my wardrobe years ago. It was oversized but slightly cropped, impossibly soft and one of those pieces that somehow worked with everything. I think we all have garments that become benchmarks, we quietly spend years trying to find them again.
R — What is it about certain garments that allows them to move effortlessly between men’s and women’s wardrobes?
W.O. — I think great design is rarely confined by gender.
A beautifully cut coat, a classic Oxford shirt or a double-breasted blazer is really about proportion and silhouette. When those foundations are right, the garment naturally becomes more adaptable.
I especially love the idea of throwing a men’s cashmere coat or oversized blazer over something more feminine underneath. That contrast creates an ease that never feels forced,it simply feels lived in.
W.O. — I’ve been searching for the perfect field jacket for years.
Whether it’s a true menswear piece or simply inspired by one, I still haven’t found the one. Because of my height and proportions, many of the men’s versions require so many alterations that they lose the ease that attracted me to them in the first place. So, for now, the search continues. (If anyone has recommendations, I’d happily take them.)
I also still think about a charcoal cashmere-cotton sweater from The Elder Statesman that somehow disappeared from my wardrobe years ago. It was oversized but slightly cropped, impossibly soft and one of those pieces that somehow worked with everything. I think we all have garments that become benchmarks, we quietly spend years trying to find them again.
R — What is it about certain garments that allows them to move effortlessly between men’s and women’s wardrobes?
W.O. — I think great design is rarely confined by gender.
A beautifully cut coat, a classic Oxford shirt or a double-breasted blazer is really about proportion and silhouette. When those foundations are right, the garment naturally becomes more adaptable.
I especially love the idea of throwing a men’s cashmere coat or oversized blazer over something more feminine underneath. That contrast creates an ease that never feels forced,it simply feels lived in.
R — What qualities do you look for in a garment before deciding it’s worth building a look around?
W.O. — Fabric almost always speaks first, followed closely by fit.
From there I think about longevity. Is it something I’ll instinctively reach for whether I’m travelling, meeting clients, attending an event or simply getting dressed for my own day?
I have a small test for myself: if it’s going in my carry-on instead of my checked suitcase, it’s probably something I genuinely love. Those are the pieces I’d be devastated to lose. They earn their place over time.
R — The best-dressed people often appear to have a strong sense of consistency rather than a constant desire for novelty. How do you think personal style develops over time?
W.O. — I don’t think personal style is something you suddenly discover, I think it’s something you edit over years.
The people whose wardrobes I admire most aren’t constantly reinventing themselves. They simply know themselves well. Their wardrobes have rhythm.
I’ve always loved accessories because they allow you to evolve your wardrobe without constantly replacing it. In these photographs, I’m wearing a turquoise necklace I found in one of my favourite shops on Portobello Road in London, alongside earrings I wear almost every day. I love that jewelry carries memories as much as it completes an outfit.
As our lives evolve, our wardrobes naturally do too. We gravitate toward different colours, fabrics and silhouettes, but certain preferences stay with us. For me, it’s always been a high-waisted, cropped trouser in a lightweight fabric with minimal pleating. They’re surprisingly difficult for me to find, so whenever I discover the perfect pair, I’ll often buy two.
W.O. — Fabric almost always speaks first, followed closely by fit.
From there I think about longevity. Is it something I’ll instinctively reach for whether I’m travelling, meeting clients, attending an event or simply getting dressed for my own day?
I have a small test for myself: if it’s going in my carry-on instead of my checked suitcase, it’s probably something I genuinely love. Those are the pieces I’d be devastated to lose. They earn their place over time.
R — The best-dressed people often appear to have a strong sense of consistency rather than a constant desire for novelty. How do you think personal style develops over time?
W.O. — I don’t think personal style is something you suddenly discover, I think it’s something you edit over years.
The people whose wardrobes I admire most aren’t constantly reinventing themselves. They simply know themselves well. Their wardrobes have rhythm.
I’ve always loved accessories because they allow you to evolve your wardrobe without constantly replacing it. In these photographs, I’m wearing a turquoise necklace I found in one of my favourite shops on Portobello Road in London, alongside earrings I wear almost every day. I love that jewelry carries memories as much as it completes an outfit.
As our lives evolve, our wardrobes naturally do too. We gravitate toward different colours, fabrics and silhouettes, but certain preferences stay with us. For me, it’s always been a high-waisted, cropped trouser in a lightweight fabric with minimal pleating. They’re surprisingly difficult for me to find, so whenever I discover the perfect pair, I’ll often buy two.
"Sometimes it’s a jacket. Sometimes it’s a necklace"
R — When putting together an outfit, what tends to come first for you: silhouette, colour, texture, mood, or something else entirely?
W.O. — Normally, it begins with one piece.
Sometimes it’s a jacket. Sometimes it’s a necklace. Sometimes it’s simply the weather.
Today, for example, Paris is reaching almost 40 degrees and I have meetings across the city, most of which I’ll be walking to. On a day like today, fabric becomes the starting point. I want something breathable, lightweight and polished enough to carry me through the day without feeling precious.
Lately I’ve been working closely with several jewelry brands, so my clothing has naturally become quieter. Neutral colours and carefully considered necklines allow the jewellery to become part of the conversation rather than competing with it.
W.O. — Normally, it begins with one piece.
Sometimes it’s a jacket. Sometimes it’s a necklace. Sometimes it’s simply the weather.
Today, for example, Paris is reaching almost 40 degrees and I have meetings across the city, most of which I’ll be walking to. On a day like today, fabric becomes the starting point. I want something breathable, lightweight and polished enough to carry me through the day without feeling precious.
Lately I’ve been working closely with several jewelry brands, so my clothing has naturally become quieter. Neutral colours and carefully considered necklines allow the jewellery to become part of the conversation rather than competing with it.
R — Are there individuals, whether from fashion, film, art, or elsewhere, whose approach to dress continues to inspire you?
W.O. — One thing I’ve realised while answering these questions over the course of a week spent travelling is that my greatest inspiration often comes from places rather than people, but the people in those places are always extremely inspiring as well.
I was recently in Venice and found myself captivated by the faded facades, weathered stone and extraordinary craftsmanship hidden inside tiny workshops. I often leave cities feeling more inspired by architecture, colour and texture than by runway shows.
That said, I’ve always admired the way Laila Gohar dresses. There’s a sense of humour and individuality to her style without it ever feeling overworked. I still look to Leandra Medine Cohen, and more recently Tal Waksal has become someone whose style I genuinely admire. We actually met while standing in line for The Row opening in Paris, and I immediately told her how much I loved the way she dressed. She’s effortlessly cool, incredibly kind, and her brand, All Three Studio, has become one of my favourite sources for elevated wardrobe essentials, both for myself and my clients.
I’ve also always admired Erin Wasson and Zoë Kravitz. What all of these women share is a sense of ease. Their clothes never arrive before they do.
Ultimately, that’s always the feeling I’m chasing: to look effortless and to feel good. And by “good,” I mean confident, calm, fresh, unique and never overdone.
W.O. — One thing I’ve realised while answering these questions over the course of a week spent travelling is that my greatest inspiration often comes from places rather than people, but the people in those places are always extremely inspiring as well.
I was recently in Venice and found myself captivated by the faded facades, weathered stone and extraordinary craftsmanship hidden inside tiny workshops. I often leave cities feeling more inspired by architecture, colour and texture than by runway shows.
That said, I’ve always admired the way Laila Gohar dresses. There’s a sense of humour and individuality to her style without it ever feeling overworked. I still look to Leandra Medine Cohen, and more recently Tal Waksal has become someone whose style I genuinely admire. We actually met while standing in line for The Row opening in Paris, and I immediately told her how much I loved the way she dressed. She’s effortlessly cool, incredibly kind, and her brand, All Three Studio, has become one of my favourite sources for elevated wardrobe essentials, both for myself and my clients.
I’ve also always admired Erin Wasson and Zoë Kravitz. What all of these women share is a sense of ease. Their clothes never arrive before they do.
Ultimately, that’s always the feeling I’m chasing: to look effortless and to feel good. And by “good,” I mean confident, calm, fresh, unique and never overdone.
"The confidence comes first, and the style naturally follows"
R — What do you think people most often misunderstand about getting dressed well?
W.O. — I think people spend far too much time comparing themselves to everyone else instead of taking the time to understand what genuinely works for them.
Great style isn’t about constantly buying something new. It’s about understanding proportion, investing in tailoring and learning how to reinterpret what you already own.
When people stop chasing trends and start building a wardrobe that reflects who they are, getting dressed becomes much easier, and much more enjoyable. I truly believe that when you walk out the door feeling comfortable in your own clothes, you carry yourself differently. The confidence comes first, and the style naturally follows.
W.O. — I think people spend far too much time comparing themselves to everyone else instead of taking the time to understand what genuinely works for them.
Great style isn’t about constantly buying something new. It’s about understanding proportion, investing in tailoring and learning how to reinterpret what you already own.
When people stop chasing trends and start building a wardrobe that reflects who they are, getting dressed becomes much easier, and much more enjoyable. I truly believe that when you walk out the door feeling comfortable in your own clothes, you carry yourself differently. The confidence comes first, and the style naturally follows.
Whitney is wearing:
