My father was passionate about vintage cars, he loved their lines. At the beginning of the book we created with C.P. Company, 1000 Miglia. Viaggio nella memoria, there’s a passage he wrote that, in my opinion, deserves to be quoted. It begins like this: 

«What were car bodies in the past, if not the clothing of the engine, just as garments are to the body? Taking part as a spectator and sponsor in the re–edition of the 1000 Miglia, this race that was once ‘epic‘, was, for me, an almost natural choice. Once upon a time, there were evening cars: sporty and elegant ones, modest and comfortable family cars, and loud ‘American‘ cars that changed lines and color combinations every year, so much so that you could tell the ’54 collection from the ’53. The automobile, like clothing, defined its owner’s identity; it didn’t just signal social status, it was a portrait of taste and lifestyle. The designers of that era knew how to blend function and aesthetics with ease and imagination.» 

Aesthetic choices that defined you, not through the price of the car, but through taste. An extension of the person: just like choosing an outfit, a car should resemble you.

Lorenzo places one of the many black boxes from the archive shelves on the desk, then pulls out a stack of papers, and just like that, we dive into another story about engines. 

In the 1990s, Piaggio contacted my father to work on a redesign of the Vespa. Sure, there were still a few design ingenuities ─ he wasn’t a product designer, after all-but the ideas were genuinely interesting. First of all, the side panels of the Vespa always got scratched. So he added rubber patches to protect them, like the elbow patches on Stone Island jackets. Then there were the turn signals, placed along the edges of the shield-something we now do with LEDs, but at the time, it was a pretty forward-thinking idea. There was also a matching vest and helmet. Even the helmet featured rubber edging to reinforce the most wear-prone areas. And finally, one of the models ─ there was a whole series ─ instead of the traditional hard top case, had a backpack. A Velcro backpack you could attach to the Vespa and then take with you once you got off. He worked on it a lot, six to eight months where this was all he thought about. And somewhere, there’s even a letter…

Lorenzo rummages through the papers. While he’s still searching for the letter, he tells us that some video content had also been shot for the Vespa project, teaser-like clips meant to present the idea to FIAT. Specifically, edited scenes from Quadrophenia, the cult British film that became a manifesto for the Mod subculture, so fond of the Vespa. Lorenzo keeps digging and something else catches him by surprise. 

This is interesting… My father always tended to expand projects a little: he had started out in advertising, as a communicator, so he naturally thought in terms of branding. He was very product-focused, of course, but always with a broader brand vision. For instance ─ he reads from a document signed by Massimo Osti: 

«Historical notes for the future: the 1990s Vespa could be the starting point for reclaiming the global image of Piaggio’s company heritage, long forgotten and unknown to most. […] Some strong connections have emerged with areas that offer clear prospects for growth and development, such as: electric vehicles, production sailing boats, and personal helicopters.» 

It’s funny, because this was 1990, and electric vehicles weren’t even on the radar. As for production sailing-my father was passionate about sailing-it was just starting to emerge back then, but still quite niche. Then, ten years later, Bavaria came along with the “camper of the sea”: a camper company that started building boats using the same logic. Molds, fiberglass, standardization, lower costs. And suddenly sailing became a more democratic sport. And finally: personal helicopters… 

He laughs. 

That one was pretty futuristic. But today? I’d say we’re not even that far off…

The letter doesn’t turn up, but we do find out what it was about: an exchange of opinions with Avvocato Agnelli regarding the Vespa in question. Meanwhile, more and more materials keep emerging: research on graphic design trends of the time, on what competitors were doing… Lorenzo admits he has to stop himself from digging into every single detail. He confesses how much he enjoys getting lost in these treasure chests of hidden gems, rather than ─ he says this with all the love in the world ─ talking only about clothes. We move on to another box, which means another story. 

Then there’s the Boxel P488. One day, my father decided to sponsor this electric race car. And here’s something interesting: he used to launch what we might now call social projects ─ or in today’s terms, corporate responsibility initiatives ─ which would then become content. Now that’s quite common, but at the time it was pretty unusual. Fashion worked only through fashion campaigns: photoshoots, models, and so on. But my father would create side projects and then turn them into content for his brands. For instance, some of these projects became catalogues. 

He pulls them out and shows them to us.

They were clothing catalogues structured in two parts. One was product-focused and featured only still-life shots. The other was more editorial in nature, but not in the sense of representing aspirational worlds. They told stories. Kind of like how today brands create collateral content to convey a set of values. Another important thing to know about these catalogues is that they were sold at newsstands for 5,000 lire, printed in a format that stuck out at the top, so they’d be clearly visible behind or above other displayed magazines. No one was selling fashion catalogues back then. 

We take a little detour into Osti’s garments to highlight another unique aspect of his catalogues. 

One of the core elements of his work, in terms of product, was garment dyeing. That is, dyeing the garment once it’s fully constructed. This technique creates sophisticated color shades and gives the clothing a slightly worn-in look. He wanted to achieve a similar effect in graphic design. So he used this system: with a color photocopier-low-res by today’s standards ─ he would photocopy the images to “dirty” them, reduce their resolution, blow them out… basically, he’d make them “wrong” on purpose. It was a deliberate effect meant to give the printed material the same patina as his garments. 

His clothes resonated at different moments in time because they were adopted by certain subcultures. First, the alternative Bologna scene of the ’70s, centered around the DAMS university program and underground comics. Then came the “paninari,” a youth subculture that especially embraced Stone Island. After that, another leap: the British football casuals, particularly from Northern England. Then again: the UK grime rap scene, followed by the American rap world ─ thanks to Drake ─ and even the scene in southern France. For a long time, we tried to understand why these leaps happened between such distant and diverse cultural groups. Working with semiotician Luca Libertini, a colleague and friend, and a professor the University of Westminster, Andrew Groves, we came to a possible answer: maybe the reason all this happened is because my father never tried to represent a lifestyle. That’s what most other brands did: if you wanted to be a certain way, you bought that product. Super-stylish models on a yacht, or riding horses across the prairies of the Wild West, and so on… all the different expressions of this kind of communication style, whether more aspirational or more participatory. My father, on the other hand, always represented the product. And when the focus is just the product, it stays open to different interpretations. It’s a bit like Umberto Eco’s idea of the “open work.” The idea is this: if you don’t depict a closed-off, defined world but just the object, then a paninaro sees one thing, a casual sees another, and for both, it can be equally meaningful. 

Let’s go back to the Boxel P488, where our detour into the catalogues began. 

In 1987, engineer Pasquini had designed this vehicle and was looking for investors. My father fell in love with the project and decided to fund it. There was a race in Rome, exclusively for prototypes (after all, we were at the dawn of electric vehicles). The Boxel was performing incredibly well. They were about to win against the electronics giants, but at the final corner, they were unfortunately pushed off the track and crashed. Pasquini would later go on to develop the actual Boxels: small electric delivery carts, essentially cuboid-shaped, with tiny wheels, that roamed the streets of Bologna for years. They were built to last, thanks to an extremely simple mechanical structure made entirely of standard components. That’s why, even long after production had stopped, they kept fixing them for twenty years using parts you could basically find at a hardware store. 

Speaking of Bologna… 

As a Bolognese myself, there’s another project I want to show you, one that made my jaw drop when I first saw it. It wasn’t my father’s project directly, but he supported and promoted it while serving on the City Council in the early 1990s. It was called the “Toro Project,” named after the geometric shape. To me, it’s absolutely mind-blowing: a plan to move Bologna’s entire ring road underground and create a four-level subterranean structure-one for traffic, one for parking, one for storage, one for shops-and then cover it all with a massive park. The concept was developed by engineer Petazzoni. At the time, traffic was perhaps even worse than it is today, and I found the idea of a green belt circling the city absolutely beautiful. Why did my father get involved in something like this? It came from his personal beliefs. He deeply cared about sustainability and urban livability. He was always strongly motivated by those values. 

Lorenzo also tells us about the project that Massimo Osti developed with C.P. Company for the Rainforest Foundation. A documentary was filmed featuring Sting and Raoni, chief of the Kayapo tribe. A commemorative T-shirt was also produced. The goal was to raise global awareness about deforestation and to provide direct support to the Amazonian tribes. 

Incidentally, the Toro Project also involved the concept of project financing. The idea was that it would cost the municipality nothing, as rental income from the commercial spaces on the retail level would cover the entire investment. They had even studied a system to carry out the work without interrupting traffic. In my view, it was a colossal project, probably oversized for a city like Bologna. But I’ve always admired it for how visionary it was. 1993. As you can see, for each of these initiatives beyond his brands, my father poured in tremendous energy. 

We ask Lorenzo whether, going through all these boxes, he ever stumbles across things he’s never seen before. Constantly, he tells us. In fact, he put aside a couple just before we arrived. 

Then we start talking about the personal cars that marked the various stages of Massimo Osti’s life. 

My father always had a passion for things from the past. The first car he ever bought was a Citroën Traction Avant, which he picked up in northern France. He drove it all the way back to Italy, so much so that his second brand, Boneville, is named after the place where, during that trip, they broke down and were stuck for two days. But the car he was definitely most attached to–because it was with us for so long–was a Porsche 356 Cabrio, banana yellow. A crazy color; I didn’t like it at all at first. Over time, I grew to appreciate it. It was a car my father never let me near. I asked a million times to drive it, and it was always a firm «no.» He kept it for years and had it restored three or four times. Eventually, he sold it: he could never find the time to use it properly, and it just wasn’t being looked after the way it should’ve been. It would sit idle for six months, something would go wrong, water would leak in, the seats would rot, and he’d have to fix them all over again… It became more of a burden than a pleasure. 

Apparently, Massimo Osti didn’t just have eyes for the Mille Miglia: 

We used to watch Formula One together, he enjoyed it. Just as he loved cars in general. I was little, so I don’t really remember, but my mother told me that over the years we had, in order: two Citroën DS Pallas ─ one after the other ─ because of his love for their design. Then, when he started earning well, he fell for this beast of a car: a Jaguar Daimler Double Six, petrol, with two fuel tanks. You’d empty one, then switch to the other. I swear I remember that when he drove fast, my sister and I used to play a game watching the fuel gauge needle drop. That was the period when he drove from Bologna to Crevalcore every day. 

He also really loved driving. He drove fast. But the funny thing is that he liked these kinds of cars, yet at the same time he was embarrassed by them. Like I said, he drove fast, but when he was behind the wheel of the Jaguar, he’d drive super slow by his own standards. Rather than get caught in public with a flashy car after doing something stupid, he would’ve rather buried himself. In fact, after that one, he switched… to a Micra: finally, a car he could relax in and have fun with.

We also had a Honda Civic 1600 with 16 valves that he really liked (and so did I). It was small, with a chopped rear end. Driving it felt like being in a go-kart. I ended up getting one too ─ we both bought ours second-hand. Though my father didn’t want me to get the 16-valve version because he thought it was too powerful. Then there were the Range Rovers, one after another, back when they still felt like something exotic. But at a certain point, he decided they used too much fuel, so he got this Toyota 4Runner, which I later converted into a camper and used for tons of trips. He was super happy and surprised by how little fuel it used. We’re talking about a 3.0 petrol engine that you couldn’t even drive today, of course it was a very different time. He needed those kinds of vehicles because he lived in the countryside, and it often snowed. So he was never into cars for the status: they always had to be functional. 

‘Function’: that word keeps coming up. 

He also had a Lada Niva, another imported car: there was this sort of ongoing research to find things you didn’t see everywhere. Once, we even tried to import a light blue 1950s Cadillac from the U.S., but it turned out to be too complicated. 

We start wondering what kind of car Massimo Osti would be driving today, and Lorenzo ventures a guess: probably some cheap Chinese car that works great, and who cares. He adds that his father had a bit of a fascination with China.

What set my father apart from almost everyone else in the fashion world was that he didn’t have a traditional academic background. His approach was very different. As I mentioned, he started out as a graphic designer in advertising. He didn’t begin with an abstract idea and then try to bring it to life. He was a practical creative. His approach was bottom-up. He would take a garment and think, «Okay, I like this, but I like that pocket better,» so he literally photocopied it ─ as you can see below ─ and attached it to see how it looked. «I prefer that zipper,» he’d do the same. Always under a functional lens, with one question constantly in his mind: «What does this garment need?» He started from existing shapes and transformed them. The Vespa project I showed you perfectly illustrates this: to update the square-lined PK model of the time, he revisited older, rounder models and added the need to make everything more functional (like the rubber patches on the side panels, the detachable backpack, and so on). We could call this creative process “transformative”. 

My father was born poor, an orphan, and lost his brother when he was young: he had a tough life. Seeing what he had managed to build with his own hands made him proud. But fundamentally, it made him a generous person; he wasn’t someone to show off or seek gratification through material things. For him, work was just work. It wasn’t about passion. «Am I doing this? Does it come out well? Am I earning from it?» If the answer was yes, then he did it with incredible determination ─ what I’d call “Osti-nation.” But it was really just hard work: a thousand times you’d ask him, «Do you like it?» and he’d say, «It’s work.» Otherwise, my father was very shy, very reserved, and again, very generous.

Let’s talk about the great friendship between Massimo Osti and Lucio Dalla, and wonder if motors might have played a role here too. Why? Because in ’76 Lucio Dalla released an album called Mille Miglia, and because in our latest Motor Valley-style guide to Bologna, we came across a beautiful photo of Dalla leaning on a Jaguar. 

It’s a stunning picture. There was probably a time when maybe they both had one. Who knows… 

Lorenzo was too young to remember anything that could definitively support our theory, but he tends to think yes, it’s likely that the imagery of four wheels was one of the many paths that connected Dalla and his father. 

They definitely influenced each other. 

Another gem adding to Massimo Osti’s uncategorizable parallel projects: Lorenzo tells us that his father designed the cover of Dalla’s album Cambio (featuring a photograph by Luigi Ghirri, the photographer we mentioned recently), while Dalla himself acted as a testimonial for a C.P. Company catalog. The brand also created a custom long silk shirt for him, adorned with a star pattern which he wore in many concerts. The icing on the cake was a Stone Island jacket lined with fur: Dalla always wore it inside out, so Massimo Osti ended up making it for him exactly the other way around.

Staying in the vibe of those years, Lorenzo talks to us about the importance of DAMS and its role as a catalyst for the many diverse talents in Bologna’s creative scene during the ’70s. 

Back then, one of Bologna’s greatest assets was DAMS. DAMS included music, art, cinema, and theater: it wasn’t focused on just one discipline. Moreover ─ just like how the University of Bologna is still organized today ─ the various faculty locations were scattered throughout the city; there were no separate campuses. This created a lot of cross-pollination among students from different fields. There’s a piece by Professor Roberto Grandi, with whom I graduated in Mass Communication at university, arguing that this very mix of the arts sparked this creative and fertile energy. On top of that, there was a strong spirit of improvisation. People just tried things out. 

Right after this artistic detour, Lorenzo lets us take a guided tour of the archive while he goes to pick up his son from school. Our conversation about Massimo Osti has been surprising, shedding light on both well-known and lesser-known facets of the life of a pragmatic visionary. If his tangible and spiritual legacy still inspires well beyond the world of fashion today, it’s mainly thanks to the work of Lorenzo and his sister Agata, who keep his voice alive. Partly through the archive they established, partly through conversations like these, and through many other communication projects (books, magazines, videos, social media, exhibitions). 

Lorenzo returns shortly afterward, and as the tour concludes, we say our goodbyes. The last image before we leave is of his son: a child sitting at a desk in the archive with blank sheets in front of him. Next to him, a painting of Massimo Osti’s face watches over. With a certain urgency, he asks Lorenzo for some colors, which Lorenzo promptly hands over. It seems the boy carries both vision and pragmatism too.