Style Talk is slowly becoming our favorite series, and for good reason. It gives us the opportunity to have more thoughtful and focused conversations with people whose style really speaks volumes. Rather than chasing trends, these conversations revolve around personal taste, habits, and the little details that shape how someone presents themselves day in and day out.
This time we spoke with Alessandro Negri, 32-year-old collector vintage clothing with a focus on military and work clothing, which is the majority Made in USA. His style is based on contrasts, combining classic pieces like leather jackets, fringed jeans, loafers and sneakers in bold colors. For him, fashion is a personal narrative, where clothes often carry a memory and meaning. Over time, his approach has vintage has become more sophisticated, and now describes himself as a "street hunter," always looking for unique pieces at markets and fairs all over the world.
Can you briefly introduce yourself to our readers?
Alessandro Negri: Hi! I'm Alessandro, I'm 32 years old and my passions are sports and fashion. I don't care too much about trends; I'm a collector vintage clothing with a particular focus on military pieces, workwear and rugged garments. My research and collection are primarily focused on archival pieces made in the USA. .
“I enjoy finding common threads between cultural heritage objects of different origins: I love Italian craftsmanship, but I have a weakness for British tailoring and my style is based on a mix of the two.” – Alessandro Negri
What is your favorite spring look?
Alessandro Negri: One of my favorite spring outfit is black D-Pocket Perfecto, which is worn over a light DoubleRL chambray shirts and heavy white cotton short-sleeved shirts. I combine it with Jean Dessel western belt and wide jeans with a hem that stays loose at the ankle. As for shoes, I opt for black loafers with tassels, and I always round off the outfit with a red bandana tied around my neck. When I dress, I like to create contrasts and explore the connection between black and different shades of blue. The secret is in the heat of the colors: I usually choose shades like red, purple, orange or yellow.
During the transitional seasons, she mostly wears cotton and denim, preferring high-quality natural fabrics like linen for their breathability and comfort. For jackets, she prefers vintage military and surplus pieces like the jacket M65 or Jungle for their practicality and layering capabilities, while vintage outerwear like the Detroit jacket also plays an important role in his wardrobe.
He usually chooses Italian-made shirts, while for short-sleeved T-shirts he gravitates towards American heavy cotton and vintage pieces from brands like Hanesa or Velva Sheena. Denim remains a key part of his style these seasons thanks to its versatility and suitability for layering. He prefers looser cuts for better breathability and comfort, and lately he's been leaning towards darker denim, saving whites and creams for the colder months.
You can read more exclusive interviews HERE.
You love wearing hats. Do you have a favorite and is there a crazy story behind it?
“"Baseball caps are essential." – Alessandro Negri
I have a real weakness for them because I see them as a combination of history and design. I am especially drawn to brands like Double RL, Ebbets Field Flannels i Ballantyne, and at the same time I love the search for the unique vintage and second-hand pieces. In the winter I switch to navy blue watch caps or bright red ones for contrast and character. For me, details like caps, hats or scarves are what really define a look and reveal personality, something I've noticed and appreciated since childhood.
What is your favorite brand of sunglasses?
Alessandro Negri: When it comes to glasses, I definitely have my favorites. I love Wayfarer because of that casual attitude, it's a classic. Then, of course, there's the Persol, which for me is inextricably linked with the legendary style Steve McQueen. Lately I've been leaning towards Walloon; I'm a big fan of their yellow lentils, which are fantastic to add vintage characteristic appearance.
Do you have a favorite brand of shoes/moccasins that you wear in spring?
Alessandro Negri: Shoes are the foundation of my wardrobe, and lately I've been wearing a lot of boat shoes from Timberland i Sebaga, with his long-standing love for Vansu, especially more playful styles like Authentics with leopard print. My collection also includes boots from Red Wing Shoes, Paraboot i Alden Shoe Company, while moccasins are from Pierre Cabot have recently become a favorite due to their comfort and design. Besides the classics, I also enjoy Solomon and models Made in USA from New Balance, while lately I've been adding a more ironic touch with vintage beach sandals and "ugly-chic" garden shoes like Plasticana Gardane.
Given his background and deep interest in the charm of vintage military and workwear, he has recently developed a strong respect for brands that produce what he describes as true „little gems.“ Among them is AV86 – About Vintage, whose pieces have become a natural part of his daily routine, from sports to academic life, adding that final, thoughtful touch to his outfits.
In particular, the 1956 Automatic model with a beige canvas strap has become his indispensable companion. It strikes a balance between functional heritage and clean, modern reliability, aligning with his aesthetic and lifestyle.
Favorite song?
Alessandro Negri: It's incredibly difficult to define one favorite song, but if I had to choose, I would say I've Got You Under My Skin. My playlist also includes artists such as Sade, Jamiroquai, Bruce Springsteen, Nat King Cole, George Michael and David Bowie.
My taste is deeply rooted in jazz, I would say, from Miles Davis i John Coltrane to Chet Baker i Wynton Marsalis, while film music also plays a big role in my daily routine. Music helps shape my mood, creativity, and even the way I dress, depending on the energy of the day.
Sees himself more as “street vendor” rather than as a traditional shopper, drawn to markets and fairs where he can browse the stalls and discover something unexpected. Although he has built many connections, especially in Tuscany, he highlights a few standouts in Milan, such as Amercantilea on Via Orti, a shop run by friends who enjoy visiting, as well as Union Madea, known for its rich selection.
More recently, he has turned to online shopping, buying from private sellers he has connected with through his Instagram profile or via Natif Heritage. Even after extensive travel and years of collecting, he feels there are still many destinations to explore, to broaden his perspective and refine what he calls his „hunting toolkit.“ At the top of his list are Los Angeles and New York City, which he hopes to visit in the near future.
Tell us more about Natif Heritage?
Alessandro Negri: Natif was born during the Covid quarantine as a creative and passion project focused on simple, versatile accessories. My philosophy is based on clean design and balanced color palettes, and the canvas bracelet „"Regatta"“ stands out as an essential piece inspired by the spirit of the sea. I also consider our navy and bright red bandana necklaces to be key pieces, especially when paired with contrasting beaded necklaces for a more distinctive look.
Is there a vintage item that you have kept for years that still defines your style today?
Alessandro Negri: My dearest vintage it is a piece Chevignon a jacket I „stole“ from my father because it carries a strong emotional connection to my roots and our relationship. In addition to it, I am deeply attached to a pink custom-made shirt that belonged to my grandfather, which still bears traces of his aftershave, a long cashmere coat given to me by a close friend with whom I had meaningful conversations, and a travel bag Louis Vuitton that my mother took on her honeymoon to Paris. Each of these pieces goes beyond clothing, they represent family, memory, and personal history.
“For me, clothes are never just objects; they are extensions of identity, carrying stories about the people and moments that have shaped me.” – Alessandro Negri
You're running away to the south of Italy for a week. What are you packing?
Alessandro Negri: Packing for a trip to the south of Italy is always a challenge, but I have a clear system. It starts with polo shirts John Smedley in white and navy blue, plus a lighter version with snaps from October Editions. I pack 4-5 shirts, from lightweight chambray beach t-shirt to linen and cotton options for evenings, along with plain white or striped t-shirts. For swimwear, I carry three suitcases, sandals Medusa, running shoes Hoka, beige Sebago platform shoes and two pairs of loafers, one elegant dark pair and a worn pair Velasca suede. The outfit also includes wide-leg jeans, chinos, linen trousers and if possible, a navy double-breasted jacket with gold buttons and a linen jacket. Accessories like belts, turquoise details, scarves and a diving watch complete everything. My suitcases are always heavy, to the point that carrying them feels like a real workout.
When asked which city or country has the best street style, he finds it hard to single out just one, as each destination stands out in its own way. For the transitional seasons, Paris and London are, in his opinion, unbeatable, with workwear and leather jackets juxtaposing with tailored suits. In winter, however, Milan takes the lead, offering a stage on which some of the world's best clothing is showcased, with men confidently pairing ecru denim with loafers even through the fog. He sees this Milanese elegance as the perfect backdrop for garments crafted by the best tailors across Italy, reflecting a deep fashion heritage. While the United States remains the heart of casual style and vintage culture, Japan, in his view, is the undisputed “Mecca” for high-quality denim.
What three things do you never leave the house without?
“"The three essential items I never leave home without are definitely my Av86 diver's watch, my turquoise ring, and my bracelet." Natif Heritage Regatta, which has become a real good luck charm for me, especially since it was handmade by my mother.” – Alessandro Negri
In your opinion, what timeless pieces should every modern gentleman invest in, regardless of trends?
Alessandro Negri: For a man who wants to invest wisely and avoid wasting money on passing trends, the focus should be on timeless icons. Every wardrobe needs a classic, functional watch to accompany his daily life, a stylish double-breasted blazer, a camel coat and a high-quality leather biker jacket.
Do you have a hidden gem in Italy that you love to escape to?
Alessandro Negri: Actually I have three, each one tied to a specific mood. When I crave charm and a piece of paradise, I turn to Capri i Grand Hotel Quisisana. It's about the exclusivity of the island, walks through nature and those unique Mediterranean lights and colors. For a light summer getaway, I go to Val Trebbia in the Apennines. It's close to home and I know it by heart. I love the wild spirit there, the smell of tanned skin mixing with the fresh focaccia, evergreen trees along the cliff and river pools to swim in. It is a place of local stories, green hills and barns, where only the riverbed changes its course over the years.
Finally, for a complete mental reset, there's Marettimo. Deep blue sea, fresh tuna, a lighthouse illuminating the Mediterranean scrub at night while deer run free and the salt on your skin. It's pure soul cleansing. I have a fourth place, the most beautiful, secret corner of Greece, but for now it remains my private island retreat.
Source: DART.hr
Photos: Alessandro Negri
