Style Talk with Alessandro Negri: How to dress for Spring

22 hours ago
8 min read

Style Talk is slowly becoming our favorite series to work on, and for good reason. It gives us a chance to have more thoughtful, focused conversations with people whose style actually says something. Instead of chasing trends, these talks revolve around personal taste, habits, and the small details that shape how someone presents themselves day to day.

We spoke with Alessandro Negri, a 32-year-old vintage collector with a focus on military, workwear, and Made in USA heritage pieces, who mixes Italian craftsmanship with British tailoring. His style is based on contrasts, combining classic pieces like leather jackets, selvedge denim, loafers, and sneakers with bold details and colour accents. For him, fashion is personal storytelling, where clothing often carries memory and meaning. Over time, his approach to vintage has become more refined, and he now describes himself as a “street hunter,” always searching for unique pieces across markets, fairs, and private sources.

Here's what we found out.

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 much for trends; I’m a vintage collector with a specific focus on military pieces, workwear, and rugged garments. My research and collection are centered primarily on Made in USA archival pieces.

“What I enjoy most is finding a common thread between heritage items from different origins: I love Italian craftsmanship, but I have a soft spot for British tailoring, and my style is all about mixing the two.” - Alessandro Negri

What’s your go-to spring look?

Alessandro Negri: One of my go-to spring looks is a black D-Pocket Perfecto, which is a numbered research piece layered over a light DoubleRL chambray shirt and a heavyweight white tubular cotton T-shirt. I pair this with a Jean Dessel western belt and wide-leg selvedge denim that stays loose at the ankle. For footwear, I opt for black polished tassel loafers, and I always round off the outfit with a red bandana tied around the neck. When I dress, my favorite thing is to create contrasts and explore the connection between black and the various shades of blue. The secret is the pop of color: I usually go for shades like red, purple, orange, or yellow.

During transitional seasons, he mainly wears cotton and denim, favoring high-quality natural fabrics like canvas cotton for their breathability and comfort. For jackets, he prefers vintage military and surplus pieces such as the M65 or Jungle jacket because of their practicality and layering potential, while vintage outerwear like the Detroit Jacket also plays an important role in his wardrobe.

He usually chooses Italian-made shirts, while for T-shirts he gravitates toward American heavyweight cotton and vintage pieces from brands like Hanes or Velva Sheen. Denim remains a key part of his style during these seasons thanks to its versatility and suitability for layered outfits. He prefers wider fits for better airflow and comfort, and lately has been leaning toward darker denim, while reserving white and cream tones for the colder months.

You like wearing hats. Do you have a favorite one, and is there a crazy story behind it?

“In the summer, baseball caps are my go-to essentials.” -Alessandro Negri

I have a real weakness for hats because I see them as a meeting point between history and design. I’m especially drawn to brands like Double RL, Ebbets Field Flannels, and Ballantyne, while also loving the hunt for unique vintage and second-hand pieces. In winter, I switch to navy watch caps or bright red ones for contrast and character. For me, details like hats or scarves are what truly define a look and reveal personality, something I’ve noticed and appreciated since childhood.

What’s your favorite sunglasses brand?

Alessandro Negri: When it comes to eyewear, I definitely have my favorites. I love the Wayfarer for that slightly bold and effortless attitude, it’s a classic that doesn't take itself too seriously. Then, of course, there’s Persol, which for me is inextricably linked to the legendary style of Steve McQueen and that timeless Italian cool. Lately, I’ve also been leaning towards Vallon; I’m a big fan of their yellow lenses, which are fantastic for adding a vintage, characterful vibe to a look.

Do you have a favorite shoe or loafer brand?

Alessandro Negri: Shoes are a cornerstone of my wardrobe, and lately I’ve been wearing a lot of boat shoes from Timberland and Sebago, alongside my long-time love for Vans, especially more playful styles like leopard-print Authentics. My collection also includes boots from Red Wing Shoes, Paraboot, and Alden Shoe Company, while loafers from Piere Cabot have recently become a favorite for their comfort and timeless design. Beyond classics, I also enjoy Salomon and Made in USA models from New Balance, while lately adding a more ironic touch with vintage beach sandals and “ugly-chic” garden shoes like Plasticana’s Gardana.

Given his background and deep interest in the charm of military vintage and workwear, he has recently developed a strong appreciation 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, considered touch to his outfits.

In particular, the 1956 Automatic model with a beige canvas strap has become his go-to companion. It strikes a balance between rugged, functional heritage and clean, modern reliability, aligning seamlessly with both his aesthetic and lifestyle.

Favorite song?

Alessandro Negri: Defining a single favorite song is incredibly difficult, but if I had to choose, I’d say I've Got You Under My Skin. To me, it represents timeless style and effortless charm. My playlist also includes artists like Sade, Jamiroquai, Bruce Springsteen, Nat King Cole, George Michael, and David Bowie.

My taste is deeply rooted in jazz, from Miles Davis and John Coltrane to Chet Baker and Wynton Marsalis, while movie soundtracks also play a big role in my daily routine. Music helps shape my mood, creativity, and even the way I dress, depending entirely on the energy of the day.

He sees himself more as a “street hunter” or an event-goer than a traditional shop customer, drawn to markets and fairs where he can browse stalls and uncover something unexpected. While he has built many connections, particularly in Tuscany, he highlights a few standout spots in Milan, such as Amercantile on Via Orti, a shop run by friends he enjoys visiting, as well as Union Made, known for its strong selection.

More recently, he has also turned to online sourcing, purchasing 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 left to explore, both to expand his perspective and refine what he calls his “hunter’s 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. What’s a must-have piece from the brand?

Alessandro Negri: Natif was born during the Covid lockdown as a creative outlet and passion project centered around simple, versatile accessories. My philosophy is based on clean design and balanced color palettes, with the “Regatta” canvas bracelet standing out as an essential piece inspired by the spirit of the sea. I also consider our navy blue and bright red bandana necklaces key pieces, especially when layered with contrasting beaded necklaces for a more distinctive look.

Is there a vintage item you’ve kept for years that still defines your style today?

Alessandro Negri: My most cherished vintage piece is a Chevignon jacket I “stole” from my father, as it carries a strong emotional connection to my roots and our relationship. Alongside it, I’m deeply attached to a custom-made pink shirt that belonged to my grandfather, still carrying traces of his aftershave, a long cashmere coat gifted by a close friend with whom I shared meaningful conversations, and a Louis Vuitton travel bag my mother took on her honeymoon to Paris. Each of these pieces goes beyond clothing, they represent family, memory, and personal history. For me, garments are never just objects; they are extensions of identity, carrying the stories of the people and moments that shaped me.

You’re escaping 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 John Smedley polos in white and navy, plus a brighter buttoned version from Octobre Éditions. I pack 4–5 shirts, from a lightweight chambray for the beach to linen and cotton options for evenings, along with plain white or striped T-shirts. For swimwear, I take three trunks, Méduse sandals, Hoka running shoes, beige Sebago boat shoes, and two pairs of loafers, one elegant dark pair and a worn suede Velasca pair. Clothing also includes wide-leg jeans, chinos, linen trousers, and if possible, a navy double-breasted blazer with gold buttons plus a linen jacket. Accessories like belts, turquoise details, bandanas, and a diver’s watch complete the setup. My suitcases are always heavy, to the point that carrying them feels like the real workout of the trip.

When asked about which city or country has the best street style, he finds it difficult to single out just one, as each destination excels in its own way. For transitional seasons, Paris and London are, in his view, unmatched, effortlessly blending rugged workwear and leather jackets with refined tailoring.

In winter, however, Milan takes the lead, offering a stage where some of the world’s finest outerwear is on display, and where men confidently pair ecru denim with loafers even through the fog. He sees this Milanese elegance as the perfect backdrop for garments crafted by the finest tailors across Italy, reflecting a deep sartorial heritage.

While the United States remains the heart of casual style and vintage culture, Japan stands, in his view, as the undisputed “Mecca” for high-quality denim and military surplus.

What three things do you never leave the house without?

“The three essentials I never leave home without are definitely my diving watch from Av86, my turquoise ring, and my Natif Heritage Regatta bracelet, the latter being a true lucky charm for me, especially since it was handmade by my mother.” - Alessandro Negri

In your view, what are the timeless pieces every modern gentleman should invest in, regardless of trends?

Alessandro Negri: For the man who wants to invest wisely and avoid wasting money on fleeting trends, the focus should be on timeless icons. Every wardrobe needs a classic, functional watch that keeps pace with his daily life, a sharp double-breasted blazer, a camel coat, and a high-quality leather biker jacket.

Do you have a hidden gem in Italy you love to escape to?

Alessandro Negri: I actually have three “places of the heart”each tied to a specific mood. When I crave timeless charm and a slice of paradise, I look to Capri and the Grand Hotel Quisisana. It’s about the exclusivity of the island, the walks through nature, and those unique Mediterranean lights and colors. For an easy summer escape, I head to Val Trebbia in the Apennines. It’s close to home and I know it by heart. I love the wild spirit there, the scent of sun-tanned skin mixing with fresh focaccia, the evergreen trees against the rock, and the river pools where you can swim. It’s a place of local stories, green hills, and barns, where only the riverbed changes its course over the years.

Finally, for a total mental reset, there is Marettimo. Deep blue waters, fresh tuna, the lighthouse illuminating the Mediterranean scrub at night while deer run free, and the salt on your skin. It’s pure soul-cleansing. I do have a fourth spot, the most beautiful, secret corner of Greece, but for now, it remains my private island sanctuary.