The Architect of Identity: A Conversation on Style with Alessandra Benedetto
By Denise Ho
At Kitdo, we see style as a language—a deep personal form of expression. So when we sat down with Italian stylist and wardrobe curator Alessandra Benedetto, we knew we were in for a conversation that would go far beyond trends.
Alessandra’s work is rooted in authenticity. She doesn't just dress people; she builds wardrobes that are "coherent, versatile, and designed to last—not to impress, but to truly work." Her approach is a masterclass in intentionality, and we were thrilled to hear her perspective on cultivating a more meaningful relationship with what we wear.
KITDO: To start, could you tell us about the outfit you are wearing right now?
ALESSANDRA: Right now I’m wearing something very “me”.
An oversized white men’s shirt (it’s actually my husband’s) slightly rolled at the sleeves. I love the ease and the proportion it gives. It feels effortless but intentional.
I paired it with toffee-colored trousers from an independent Italian brand that works with deadstock fabrics. The color is warm, almost caramel, and the fabric has just enough structure to hold the line without feeling stiff. On top, a black leather bomber. It gives the look a bit of tension (sharp, clean, slightly masculine). Around my neck, a vintage black-and-white Chanel silk scarf that belonged to my grandmother. It’s light, delicate, and full of memory. I like mixing something personal and soft with something more graphic.
I’m carrying a suede Tom Ford for Gucci bag in rich brown tones, with a wooden handle (sculptural, almost quiet but very strong). I’m wearing several vintage rings, and square-toe brown ankle boots that I honestly wear all the time. They ground everything. It’s simple, but layered in texture and meaning. 
KITDO: We love your content and your tips for dressing with elegance. Could you describe a time you reinvented a garment to create a look that felt deeply personal and unique?
ALESSANDRA: Thank you!
I’ve always loved wearing clothes in ways they weren’t originally designed for. I think that’s where elegance becomes personal, when you shift something slightly and it suddenly feels yours.
One look I really loved was wearing a wool tank top backwards, almost like a vest. The neckline fell differently, the back became the front, and it created this unexpected line that felt subtle but strong. I often do the same with shirts, turning them around, playing with the buttons, adjusting the collar so it frames the neck in a new way. For me, reinventing a garment doesn’t mean transforming it completely. It’s about asking: “what else could this be?” That’s usually where the most personal version of style begins.
KITDO: As a stylist, what guides you in building a wardrobe that is not only versatile but can be creatively adapted to different facets of your personality?
ALESSANDRA: When I work with clients, I always go beyond the surface. I’m not only interested in how they see themselves or how they want to appear. I want to understand how they feel, and how they want to feel in their clothes. That’s the real key.
When you’re clear on how you want to feel, you stop attaching your identity to just one style, one silhouette, or one aesthetic. Those give you only one dimension of who you are. But we’re never just one thing. We’re structured and soft. Professional and sensual. Minimal and expressive. Once you connect to those different facets of yourself, the wardrobe becomes a set of tools. Individual pieces (and the way you combine them) can help you access different versions of who you are, without losing coherence.
This is where creativity opens up. Because instead of thinking “this dress is only for the evening” or “this blazer is only for work,” you start thinking in terms of qualities. This dress gives me fluidity. If I pair it with something structured, it becomes urban and sharp. If I soften it, it becomes intimate and relaxed.
When you understand that clothes are tools (and that different combinations create different emotional results) you stop limiting yourself to one or two fixed outfits per context. You gain freedom, but it’s a conscious freedom.
So what guides me is always this: clarity about identity and emotional intention. Once you know who you are and how you want to feel, versatility becomes natural, and creativity becomes aligned.
KITDO: For someone looking to develop their own personal style, what is the most important place to start?
ALESSANDRA: Your own wardrobe.
It may sound simple (almost too simple) but it’s incredibly underestimated. The first instinct is usually to look outward for inspiration, trying to “find” your style somewhere else. But the truth is, you already have one. It’s just not always clear or organized.
The real work begins with observation. Look at what you actually wear, not what you think you should wear. Notice the patterns. Which pieces do you reach for repeatedly? Which combinations feel natural? Which colors and fabrics make you feel comfortable or confident?
At the same time, pay attention to what you don’t wear, even if you once loved it. Those untouched pieces are just as informative.
When you analyze your wardrobe this way, you gather real data about yourself. You begin to understand why certain silhouettes, materials, or color palettes resonate more than others. From there, personal style can evolve intentionally. Through research, experimentation, and refinement. But the first step is always close to you. You don’t need to search far. Your style is already there, it just needs clarity and structure.
KITDO: What is your favorite look you've created with Kitdo, or your favorite go-to way of wearing it?
ALESSANDRA: There was one look in particular that really stayed with me. I wore an oversized blue shirt backwards, styled with Kitdo, black jeans with fringed hems, and simple sandals.
It felt very Phoebe Philo-coded: understated, intelligent, slightly subversive. Nothing dramatic. Just a small shift, but that subtle change completely transformed the attitude of the look. I felt like the cooler, sharper version of myself.
That’s what I love about Kitdo.
My go-to way of wearing it is to drape a shirt or a knit with it. I naturally gravitate toward masculine, classic pieces and Kitdo’s organic yet modern shape introduces a feminine tension that feels incredibly balanced. It gently defines the silhouette, adds softness and intention, and transforms something traditional into something more contemporary and personal.
It never overpowers the outfit. It simply refines it and that’s exactly why it works so well for me.
As Alessandra reminds us, style isn't something you find but something you uncover in your own closet—and Kitdo, for her, is simply a tool that helps refine that story. Follow Alessandra at @alessandra.personalstylist
Next time you get dressed, ask yourself her question: How do I want to feel?
