Three years ago, I stood outside a café in Florence during Pitti Uomo, watching a group of American buyers squint at passing Italians with the concentration of anthropologists discovering a new tribe. “See how his jacket’s completely unconstructed?” one whispered reverently. “That’s the real European look.” His colleague nodded solemnly. Meanwhile, about twenty feet away, an actual Florentine businessman hurried past wearing a suit with shoulders so structured you could’ve balanced your espresso cup on them. I nearly choked on my macchiato.
I’ve spent a good chunk of my career nodding sympathetically while American guys tell me exactly what “European style” is, usually while they’re wearing something that would make an actual European burst out laughing. The mythologizing of continental style has created a bizarre alternate reality where every Italian is born with the ability to perfectly tie a scarf and every Frenchman innately understands the precise shade of navy that best complements his complexion. Yeah, I hate to break it to you, but I’ve been to Paris. There are plenty of French guys wandering around in terrible jeans and tourist t-shirts. They’re just, you know, regular people.
But I get it – I really do. For decades, American men’s magazines (mine included, I’m not innocent here) have sold this mystique of the effortlessly stylish European man. We’ve created this character – part Marcello Mastroianni, part Jacques Delon, with a dash of young Jude Law – who somehow rolled out of bed looking like he’s stepped out of a Fellini film. It’s all supposedly “sprezzatura” – that maddeningly overused Italian concept of studied carelessness. Except the irony is that most American guys trying to achieve sprezzatura look like they spent three hours getting dressed with a protractor and color wheel.
Let me set the record straight on a few things:
First, not all European style is created equal. A Milanese banker dresses nothing like a Berlin graphic designer who dresses nothing like a Madrid lawyer. When American men say “European style,” they usually mean “wealthy Northern Italian style from luxury brand advertisements,” which is about as representative of actual European dressing habits as a Ralph Lauren ad is of how ranchers dress in Wyoming.
I learned this lesson the hard way during my first trip to cover Milan Fashion Week back in 2011. I’d packed what I thought was a perfectly continental wardrobe – trim chinos, spread collar shirts, loafers, and knit ties. I felt like an absolute fraud the minute I got there. The Milanese guys I met didn’t dress like some unified army of sprezzatura soldiers – they dressed according to their profession, personality, and sometimes just what was clean that morning, exactly like Americans do.
My friend Marco, who runs a small leather goods shop near the Duomo, laughed at me over dinner when I confessed my pre-trip anxiety. “Jackson,” he said, passing me a plate of risotto that I’m still having dreams about, “the difference is not that Europeans have better style. The difference is that our clothes actually fit.” And honestly, he nailed it.
Which brings me to what American men often get wrong: the basics. Sorry, guys, but it’s true. We talk endlessly about pocket square folds and the pros and cons of Goodyear welting, but many American men still wear dress shirts that billow like sails and pants with enough excess fabric to clothe a small family. I’ve watched countless guys drop thousands on a prestige European label suit, only to keep wearing it two sizes too big because they think that’s “comfortable.”
The European approach – north to south, east to west – tends to prioritize fit above all else. Not skinny fit (another American misconception – we took the trim European silhouette and went overboard with it until guys looked like they were wearing their little brother’s clothes). Just… clothes that actually conform to the human body. Revolutionary, I know.
And shoes. Good lord, the shoes. I’ve lost count of how many otherwise well-dressed American men I’ve seen sporting those awful square-toed rubber-soled monstrosities that look like they were designed for a middle manager in 1997. European men generally understand that shoes matter, perhaps more than any other element. I once watched a Roman shopkeeper look a customer up and down, his gaze stopping at the man’s beautiful bespoke suit, crisp shirt, and then… sketchy discount loafers. The shopkeeper’s expression of pure, undisguised horror will stay with me forever.
But here’s what Americans actually do right, and it’s something my European friends regularly admit when we’ve had a few drinks: we understand comfort and practicality. American men have given the world genuinely innovative casual wear. While Europeans were still figuring out what to wear on weekends when suits weren’t required, Americans had already perfected comfortable, durable casualwear.
I remember shopping with Alessandro, a fashion editor from Milan, during his first trip to New York. We stopped at a classic American workwear store, and he kept touching the canvas jackets and selvedge denim with a reverence usually reserved for Kiton suits. “This is the real American style,” he said. “Honest clothes.” He bought three jackets and a pair of boots that probably weighed more than his entire Italian wardrobe combined.
That authentic American ruggedness – from heritage brands like Filson, Carhartt, and Red Wing – has ironically become highly coveted in Europe. The Japanese spotted this appeal decades ago, meticulously reproducing and perfecting American workwear to an almost obsessive degree. Meanwhile, half the guys I know in Brooklyn are desperately trying to dress like fictional Italian aristocrats.
Here’s another American strength: we’re not afraid to dress for comfort. European tradition often demands a level of formality that can be exhausting – and sometimes impractical. I’ll never forget sweating through meetings in Rome in July, watching Italian men somehow remain perfectly composed in wool suits while I gradually melted into the furniture. American men pioneered the concept that clothes should work with your lifestyle, not against it.
And we innovate. While classic menswear tends to change at a glacial pace (as it arguably should), American brands have consistently pushed technical fabrics, construction methods, and silhouettes forward. The European approach to menswear sometimes feels preserved in amber – beautiful, but static.
The healthiest approach, I’ve found, is a sort of transatlantic style exchange program. Take the European attention to fit and proportion, the emphasis on quality over quantity, and the willingness to invest in key pieces. But incorporate the American sensitivity to comfort, functionality, and individual expression.
Some specific myths worth busting:
All Italians have their suits custom-made. Nope. Most buy off the rack just like Americans do.
Europeans don’t wear athletic gear in public. Tell that to the German guys I see running errands in Adidas tracksuits.
All European men know how to perfectly match colors and patterns. I once saw a French guy wearing purple cords with a green patterned shirt and orange socks. Fashion victim knows no nationality.
I’d also like to address the bizarre American obsession with rules supposedly followed in Europe. You know the ones: “Never button the bottom button of your suit jacket.” “Never wear brown in town.” “Never wear pocket squares that match your tie exactly.” While some of these have historical bases, they’ve become almost religious doctrine for American menswear enthusiasts, while actual Europeans often approach them with much more flexibility.
The truth is, great style isn’t about which continent you’re from—it’s about understanding your own body, lifestyle, and context. The best-dressed men I know, from Chicago to Copenhagen, share a common trait: they’ve developed a personal style that feels authentic rather than cosplaying someone else’s cultural identity.
So, by all means, incorporate elements of European style that resonate with you. Appreciate the craftsmanship of northern Italian tailoring or the relaxed elegance of the French Riviera. But don’t treat “European style” as a monolithic aspiration or a costume to don.
And for God’s sake, make sure your clothes fit. That’s the real secret that crosses all borders. That, and throwing out those square-toed dress shoes. Seriously. Today. I’m begging you.