Men of Milan, Can I Be Your Wardrobe Twin?
09.29.17

Street style doesn’t really do it for me anymore, not the way it used to. I still enjoy looking through it. I love seeing what women of all sorts do to “step their game up” for fashion shows, for photographers, for their jobs — whatever the reason is. But, maybe because I work in the industry of fashion, there’s no more mystery around this part of it for me. There’s no novelty. I want to know about the people who dress up to the tens to do boring things like run errands. I want to know about the people who take supreme joy and care in getting dressed for no reason at all.

I thought about this while in Milan on business during the tip of Milan Fashion Week. Before I packed, I asked my friend Gabby, a publicist who’s an international fashion week pro, how “heavy on the looks” I should go. “People go all out in Milan,” she said. “It’s nuts.” I didn’t really pack accordingly because I’m lazy and more than anything, scared at all times of being hot or cold — so that took priority. When I arrived, I realized she was right. The women, many of whom I see all the time in New York, were dressed to the elevens, the twelves, the thirteens. See the slideshow above for proof. Everyone looked amazing. No outfits were spared because each day called for occasion.

But it was the men who caught my attention. Not just because I’m a creep! The men of Milan — the ones going about their days, who didn’t necessarily have anything to do with women’s fashion week, who didn’t get shot by street style photographers — dress beautifully. It’s almost a cliché, isn’t it? A “beautiful Italian suit.” I’ve no clue what brands they wore or what they actually did for a living. All I saw was how carefully they seemed to have put themselves together that morning. There was so much attention to detail: the way the arm of a pair of reading glasses hung over a pocket, the fold of a scarf. They weren’t even all particularly “sharp.” Like this guy, for example, the only one I thought to sneak a photo of.

Milan street style!!!

A post shared by Amelia Diamond (@amilli0naire) on

Not the most tailored of men, but I just loved his yellow pants and his superfluous (it was a hot day) candy-striped shoulder-sweater. I wanted to tap his shoulder and ask what the hell he got so dressed up for, but it was more fun to imagine that the answer was “no reason.” It’s more fun to imagine that he’s a very fashionable dad.

I ended up scrapping the fussy outfit I packed for my last day and took a cue from the Italian men I’d been observing. I wore a blazer, a button down, white jeans, loafers. It was hardly revolutionary, but it felt like an outfit. I imagined this is how my grandfather must have felt each time he tied a tie, not because it was required of him, but because he liked the look.

When I returned to New York, I called in a few new blazers and suits — two from Ralph Lauren, one from Tibi — to play a bit of experimental copycat dressing. I wanted to live in this aesthetic for a bit, to see if it worked back home in New York, in my West Village neighborhood, land of wide brim brunch hats and athleisure. As it turned out, not once did I feel “overdone,” the way I might in a dress or a wild jacket or a full runway look. Instead, I felt…handsome? Like a Roman nose. Or, for the sake of this story, a Milanese man.

Feature photo by Nataliya Petrova/NurPhoto via Getty Images.

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  • Hilary

    “I didn’t really pack accordingly because I’m lazy and more than anything, scared at all times of being hot or cold” — saaaaame every day.

    I adore menswear so this article is speaking to me & super inspiring!!! Love your experiments. The Tibi suit is SO GOOD.

  • tmm16

    I’m obsessed with menswear lately so this post made me v happy. I just daydream about wearing a plaid blazer and trousers all fall and winter. Already planning my shopping picks (for next paycheck, obvs)

  • Harling Ross

    Can you wear these outfits every day all the time ? i think they are your capsule wardrobe now.

  • I love when men have great style! This reminds me of one of your other street style posts from Italy – all the men were far better dressed than the women!

    My father is a snappy dresser, circa 1940, and my mother calls it his “costume.” But as I’ve gotten older I realize that he has real style! The only man I’ve even met to garden in white linen pants, I’ll take put together over underdressed any day!

    http://www.shessobright.com

  • Maggie Lanham

    Amelia, you were made for those double-breasted blazers. Both of those are my favorites. And the ascot! So good!

  • Julia

    I studied abroad in Milan for a semester and it was impossible to compete..seems I was taking the wrong approach by trying to imitate the women of Milan rather than the men

  • Great style for men!
    https://jamielooks.com

  • patrickdiloreto1

    am I your muse?!?

  • Nordgreen

    Love this elegance!

    https://nordgreen.com/