88th Company at Pitti Uomo: The Journey of Whisker Jack in Florence

Acouple of months ago, Andres contacted me with a simple proposal.

He was planning to attend Pitti Uomo in Florence and asked if I would be interested in sending one of my bags along for the journey. In return, he would wear it, photograph it, and share it with his audience—and with the people attending Pitti.

Before going further, it is probably important to explain why Pitti Uomo matters in the first place.

Pitti Uomo is held in Florence twice a year and is one of the most important gatherings in the world of menswear. What started as a trade fair has grown into a global meeting point for designers, buyers, photographers, and enthusiasts of style, craftsmanship, and heritage fashion. Over time, it has become especially known for the way people dress during the event, with the streets of Florence turning into an open-air showcase of personal style, tailoring, and creative expression. For anyone into heritage menswear, workwear, tailoring, or military-inspired design, Pitti has become one of those reference points you naturally look at.

Honestly, I didn’t have to think about it for very long.

Pitti Uomo has been part of my vision board and one of my dream destinations to showcase my work for the last couple of years. Life had other plans so far, but it is still something I would love to experience one day.

So when Andres reached out at that moment, sending the bag just felt right.

From the beginning, what I appreciated is that he was very considerate and respectful of the work behind the piece, which already made it easy to move forward.

What made it even more interesting is that I had actually been following Andres for a while. I first discovered him through Pinterest, then on Instagram, and over time I even found myself asking him about small details in his outfits, like watches that caught my eye.

So when he eventually contacted me about one of my bags, it really felt like a full circle moment.

And just like that, Whisker Jack was on his way to Florence.

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hisker Jack came to life thanks to my lifelong love of cats.

Ever since I was a child, cats have been part of my life. What fascinates me most about them is that they never feel like ordinary pets. They have personalities, routines, and attitudes. In many ways, they already feel like characters waiting for a story.

When I created the Vanguard world for 88th Company, I started wondering what role a cat could play in it.

The Vanguard world is filled with adventurers, pilots, sailors, racers, and explorers. It is a place where craftsmanship, machines, style, and a sense of purpose all come together. A world where heroes travel between extraordinary places and leave things a little better than they found them.

A sailor felt like the natural answer.

Historically, cats spent centuries aboard ships, helping sailors deal with rats and mice while becoming part of life at sea. In a way, cats have always been sailors in their own right.

That idea became the foundation for Whisker Jack.

I imagined him as a seasoned sailor with a diver’s watch, sailor trousers with the button details, and a heavy wool sweater inspired by the practical clothing worn by mariners and submariners.

There was one final detail that brought him to life.

Whisker Jack carries a large cigar marked with three X’s, a small nod to the larger-than-life sailors and old comic-style adventurers that inspired me growing up. There is a bit of Popeye energy in him, mixed with old maritime stories and vintage illustrations from the early twentieth century.

The cigar was never about smoking. It simply felt like part of that visual language. And it gave him that extra attitude—the kind you expect from a sailor who has been around for a while and seen a few things.

Once everything came together, the character almost felt like he created himself.

He looked like he belonged on a submarine, quietly moving through the world and collecting stories along the way.

And his first real voyage ended up being Florence.

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nce Whisker Jack was on his way, I just waited. I’m not really the type of person who keeps checking in or pushing updates. When I work with someone, I prefer to let them do their thing. With Andres, that felt natural from the beginning. Even though we didn’t speak the same language very well, he always made an effort to communicate clearly and carefully, and that mattered a lot. It made the whole process smooth without needing many words.

As Pitti got closer, I started feeling a bit nervous.

A few days before the event, I wondered how it would all look in real life. Whether the bag would fit in, whether people would notice it, whether the character would make sense in that environment.

Then he sent me a short video of the outfit.

And honestly, that was the moment everything clicked.

The shoes, the pins, the tie, the shirt, the jacket—everything worked perfectly together. And the bag didn’t feel forced into it at all. It just belonged.

After that, I stopped worrying completely.

And I was right.

Over the next days, photos started appearing from different photographers, magazines, and Instagram accounts. Every new post felt like another small chapter of Whisker Jack’s journey.

It’s been genuinely exciting to see.

A big thank you to Andres for everything he put into this—from carrying the piece to styling it so well, and for giving Whisker Jack such a strong first journey in Florence. It really meant a lot.

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s I looked back at everything, one thought kept coming up. Many of the people who inspire me don’t just create products—they create worlds.Ralph Lauren builds entire universes around his work. Hayao Miyazaki does the same through characters and storytelling. One of my favourite films is Porco Rosso. So there is something quite nice about one of my own characters ending up in Italy. I wasn’t thinking about that when I created Whisker Jack, but seeing him there made me smile. In a way, it felt like a small circle closing quietly.

For a long time, 88th Company has drawn inspiration from naval history, aviation, military heritage, and craftsmanship.

That will always be part of it.But recently, I’ve felt more and more drawn to creating my own characters and building my own world.That is where Vanguard comes in. Seeing Whisker Jack out in the world has honestly given me more motivation to keep building that direction.t feels like people are open to new stories, not just old references—and that’s really encouraging.

If you want to explore more, you can check out the Vanguard Worlds section on the website.

And if you’re new here—welcome aboard 😊

Thanks for being here and following along.

Fair winds and following seas, sailor ⚓

— Sonia 😊