Italian Icons: Stefano Pilati
The Italian icons who inspired my sense of style
Hello, my dear readers, and welcome back to The Inside Pocket!
I hope your week is being gentle with you. If that’s not the case, grab a hot cuppa, take a moment for yourself, and please enjoy this reading.
I am pleased to return to the Italian Icons series, where we will uncover the Italian divas who have inspired not only my sense of style but also shaped the very foundations of who I am and what I love.
From Monica Vitti to Monica Bellucci, today’s icon is a man! We are talking about the one and only Stefano Pilati.
Who is Stefano Pilati?
Stefano Pilati (born 1965 in Milan) is an Italian fashion designer best known for his tenure as the creative director of Yves Saint Laurent (2004–2012). Before YSL, he worked alongside some of the biggest names in Italian fashion, such as Armani and Miuccia Prada, at both Prada and Miu Miu, where he gained a reputation for fabric development and modern tailoring.
As you can imagine, considering the very name of this publication is linked to the magic inside pockets in blazers, Stefano is particularly significant to me due to his tailoring creations. In his career, he often aimed to blend menswear with femininity—something that I always strive for in my personal style. At YSL, he revived the house's sharp and sensual aesthetic with the iconic Le Smoking suit.
To give you a little demonstration of why I loved his work at YSL, I wanted to show you the short dress below, where Stefano, by playing with proportions, gave women the pleasure of a smoking suit with a strong leg moment. So. damn. cute.
After his seven years at Yves Saint Laurent, Pilati was replaced by Hedi Slimane in 2012. Pilati's collections were often met with mixed reviews, but what I truly believe is that he was just ahead of his time.
After leaving YSL, he became head of design at Ermenegildo Zegna Couture (2012–2016). In 2017, he launched Random Identities, a brand dedicated to gender-fluid, minimalist fashion. With a focus on accessibility, everyday tailoring, and non-conforming silhouettes, the label reflects Pilati’s continuous evolution and his belief in breaking down traditional fashion norms. The brand, in fact, has become quite popular for his male heels and genderless skirts, showcasing his commitment to abandoning all the conventional gender stereotypes you can think of.
In a recent episode of the podcast Fashion Neurosis—which, by the way, is the best fashion-related podcast out there (!!!)—Pilati shares that his passion for fashion ignited at the tender age of six. With his strong Italian accent, which truly feels like home to me, Pilati talks about his personal approach to design, particularly his efforts to just be oneself, and I truly, truly loved it.
One moment I particularly enjoyed in the podcast is when he mentioned that, back in the day, Tabis were not available in large foot sizes, making them pretty inaccessible to men. That’s why he had to request a custom pair for his size 46 feet. Maybe also the reason why he wanted to create a heel that could fit a man’s foot?
I highly recommend watching the episode here, and in case you need more podcasts of this type, you can always consult my list below. :)
Stefano Pilati’s Hits at Yves Saint Laurent
Some of Pilati’s hits at YSL are still remembered today, like the Tulip Skirt, which became an unforgettable signature silhouette, and accessories such as the YSL Muse Bag and, of course, the Tribute Sandal—both of which now have cult status. What I love about his collections at YSL is the dramatic draping and the ultra-sharp tailoring, which gives a strong sense of elegance and that fearless, invincible look à la YSL. I believe that what Pilati did at YSL was actually in line with the house codes, with just the right amount of his own personality injected into it. A balance that is hard to see in an era where Valentino is too Alessandro Michele and Gucci is…well, too bland?
I remember dreaming about his Muse Bag and cutting it out from magazines to add it to my magic book of desires—a very rudimentary version of my current wish list. Now it’s lost in the cupboards of my childhood room back in Sardinia, but I still hope I’ll be able to find it one day. And if I do, you’ll be the first to know.
Worth a mention
In October 2024, Pilati collaborated with Zara to launch an exclusive capsule collection featuring around 50 men’s and 30 women’s designs. Photographed by Steven Meisel, the campaign featured Gisele Bündchen and Pilati himself.
I have to admit, I’ve always had mixed feelings about these high-low collaborations. On one hand, it’s thrilling to see a designer’s vision reach a wider audience. On the other… is it giving away that magic a bit too much? You know what I think of Zara and the ultra-fast fashion it embraces. Zara dipping its toes into ‘high-end’ collabs feels a bit like McDonald’s trying to serve Michelin-starred dishes—ambitious, but are we buying it?
Either way, the collection was actually good, and celebrated during Paris Fashion week—though I personally perceived it as yet another desperate attempt from Zara to join the semi-high-end clothing landscape. I couldn’t find any data on how well it actually sold. If you do, hit me up please, I would love to know!
On this topic, I am dying to ask you—how do you feel about fast fashion collaborating with big names? And what’s the sentiment around fast fashion in general?