Is Milan the Most Stylish City in the World?

I am envious of any country (or locale) where their men don't dress like forever frat bros, wannabe rockers, or slobs.

I don't really pay that much attention to what people are wearing. It's not THAT important.

No. Paris and Rome top Milan. I mean when a stylish man wants to be REMARKABLY stylish. Milan is pretty conservative.

Take your suited man, I'll take a guy dressed like this anyday.

Sorry!

I like the young male peacocks in more Mediterranean cities than Milan. It's nice to have some flash and sex mixed into the look. While still keeping it reasonably classy.

I worked for an Italian fashion house in NY. I would talk every day to the guy in Italy who did my job there. Our straight CFO in NY once had to go to do some work in the Italian office. I overheard him say to somebody this guy looks like a movie star. I then went to Italy to do some work and got to meet him. When I finally got to see him I almost wanted to say to him why are you wasting your time here? Why aren't you a model in Milan?

R3, sorry I live in Rome and that is very much not the case. Rome is very conservative clothing wise with most suited men working in politics. Milan is very fun and fashionable. Siena is too. And Verona has more men's cool shopping boutiques than women's it seems. Although men in major European cities dress better than Americans. I can't say much about Paris, but I do know that Milan is the Men's clothing capital with it comes to the fashion world. The best men's designer shows are there.

Milanese love clothing as much as Americans love football, and treated much in the same fashion. And here you have very dapper men probably all filmed on Via Monte Napoleone, the main high-end shopping artery of Milan. Of course you will see the best of the best there. But everything from this to even streetwear is worn with a certain sprezzatura you won't find anywhere else except for Italy. It really is in their blood and taken seriously - how you present yourself in public is important. The city of Siena is similar to Milan. People go for more cool streetwear there, but the boys are conscious of how they look and enjoy having fun with what they put on.

The thing I love about living here is that it is not a youth driven culture. Older men are admired and looked up to. Younger men seek to emulate them with the way the pay attention to their own clothes. You won't see 45 year old men dressing like 17 year old skateboards. You will NEVER see gym shorts, basketball shorts, baggy hoodies or sweatpants or shower shoes with socks. Sloppy is not the way to go. From hair to shoes, they care about how they look very much.

This short video was taken just walking through Siena, 10 minutes. I wasn't looking for anything in particular. I just kept my camera on an walked. The boys there are so cute, a little rougher and sexy at the same time. I love the way they dress.

Milan is the Fashion Capital of the World. All the major Italian fashion houses are based in Milan. Prada, Versace, Armani, Dolce & Gabbana, Valentino, Luxottica, etc., so naturally the Milanese must dress the part.

And let's not forget: They're POC!

Some of these outfits are a little too much but at least they’re trying to dress well and it’s better than baggy sweatpants.

Maybe if I had somewhere to go I’d wear fancy clothes…. But jeans and a sweatshirt are fine for working from home and the occasional trip to the grocery store.

honestly for the next 20 days only I am Nerazzurri😔🙏🙏🙏🙏sempre Inter

That's refreshing, R8. Wr need more of that in the world.

Yes. There were so many good-looking, stylish men - even the older ones - that I was kind of shocked.

I prefer my men without clothes.

I see a lot of man purses.

The Italian men are attractive in general, yes. But the saying "The clothes make the man," does go a long way. The same man in a suit has a different sexy vibe than that man in a uniform or the same man in blue collar garb. Each can have their own appeal. Clothes play an important part in communicating to the world exactly who you are as a person. If your clothes are baggy, saggy, slovenly, it just really reflects that you don't care about how you look or don't care about clothes at all - which might be exactly who you are. It just looks lazy, which might be exactly who you are as well.

It really doesn't take much effort at all. The same H&M that sells the sweatpants and a hoodie will sell comfortable chinos and t-shirt that fit for about the same price. You definitely don't have to go all out like the men in the video. A little difference has a huge impact on how you are received by the world. And not just that. It will have a huge impact on how you feel about yourself, how you carry yourself. Clothes do have the power to transform - even though we like to pretend they aren't important.

One thing I have gotten as an American living abroad is a better understanding of who we are as Americans, our cultural identity. We prize the Lone Wolf - a very independent, solitary person. The idea of going out on the frontier, just you and a gun and creating a life from nothing and seizing your destiny is sewn into our national character. We love a great rags-to-riches story because that is the American dream. It's who we are. And that is not a bad thing at all when it comes to teaching the world what ingenuity, self-reliance, motivational thinking, optimism, a real "go-getter" attitude looks like. That is what the world actually prizes America for.

On the flip-side this turns vulnerability into a weakness, the idea of needing anyone else but yourself to make things happen in your life. It also makes caring about things, like the way you look, a weakness. We don't want to show the world what we really care about because it gives them the ability to target those things. We say things like, "I don't care what anyone else thinks," which is a lie. Human beings are social animals, we feed off of each other- of course we care. The balance is not letting what other people think of you paralyze you moving forward in your life. You can listen to other people yet cultivate a unique style that expresses you.

Other cultures don't have the hangups about needing other people, or openly demonstrating a love for the things they care about. It's not a source of judgement or ridicule. Men can kiss their best friend's face because they actually do love them and not have it be seen as gay. They can put on nice clothes and parade about without it being seen as trying too hard, or again, gay. It's OK not to know how to do everything yourself, and they seek each other out for help to better themselves.

So I think when someone says, they don't care about clothes or it's not important to them, I think they are just afraid of showing they don't know how to dress themselves and don't want to ask for help. Or if someone dresses slovenly on purpose, baggy clothes, pajamas in the street, flip-flops, sagging pants, it's their way of expressing the very American sentiment of "I don't care what you think of me" and are afraid to show that they actually do care very much.

All the major Italian brands are not headquartered in Milan. Gucci and Ferragamo are in Florence. Fendi and Brioni are in Rome. Brunello isn't in a major city.

You are right r20. Even Valentino is in Rome. But they all show in Milan, not their respective cities. When they come together to show the world what they have done, it's in Milan.

It's like a parade of peacocks, all plumage out. I appreciate their style but I also think they look a little ridiculous. I imagine them spending inordinate amounts of time trying to figure out how to impress other people on the street, also breaking the bank to have the most exotic sneakers or the latest hat. Silly.

I visited Italy in 2012, and Milan generally struck me as stuffy and insanely expensive. But the thing I dearly loved in Milan was Kilo Fascion, which was kind of Century 21 for the Italian designer labels. They sold leftover clothes from the major Italian houses literally by the kilo. Bought a killer cashmere sweater for 12 bucks.

Are they still around?

To the person who defend northern Italy over Rome, and other Southern Italian locales. The fashionistas of Northern Italy are only one way for a man to be stylish. I still prefer the classic stylings of Rome, Naples, Palermo, etc.

You could argue Armani and Zegna are superior to Brioni and Battistoni, but I disagree.

Let's face it, "casual" and dressing a slob are divided by a fine line, and in either case it's easy, so we can see why many men would prefer it, apart from cultural issues: Simple laziness. The old saying is, "Eat to please yourself but dress to please others", and if you're smart, you'll follow this.

R25 "eat to please yourself" sounds like dangerous advice for some, though...

All major cities have a degree of style to them, it’s just different in each place, I don’t know if you could say one is more stylish than the other. It’s whatever aesthetic appeals to you.

It’s how you put this stuff together, if you’re head to toe in dolce and gabbana that doesn’t really say stylish to me unless you’re going for something really over the top in which case it can be….it’s more about being purposeful with it. IMO the Italian brands are a little stuffy for a 20s / 30s even 40s guy, and you’re better off sticking to the more modern brands like martine rose or GMBH or Palace or Vetememts in terms of euro, or balenciaga / Prada if you have the budget, and the US kind of ironic flame / moto / skate stuff thrown in like stussy or ERL.

US style shouldn’t be discounted, the LA type of lux slobwear (for want of a better term) is really having a moment, so some James Perse or elder statesman is also nice to throw in. Also there’s a bunch of young gay designers around doing fun tees like Phlemuns and so on so it’s nice to do a mix. And ofc every ‘cool gay’ worth their salt always has some carhartt item on these days in terms of the whole workwear = sexy.

As some who lived in Italy for many years I second what R8 wrote.

One thing to point out is that young Italians don't spend as much on clothes as it might appear. They'll shop at popular priced places like OVS, H&M, Benetton, but they know how to pick out the right things and most of all, they're concerned about fit over everything. Italian men like their clothes fitted closely to their body, it creates this sleek look. And Italy has good barbers. It's the land of the great hair-cut.

Oh...and people tend to be slim. Young and old. People look healthy. Lots of nice skin color and thick hair. In the US you see lots of haggard looking people, grey complexions.

Stand back, fellas, the cognoscente 🙄 has arrived. Very persuasive, and what's more, he's 68 looks 38.

R24, that maybe fine and well, but I actually live in Rome and work in fashion. Rome's style I would equate to Philadelphia or DC. It is not a fashion city. And when I say fashion, I don't mean over the top style like the men above. I am talking about the average man on the street and their overall sense of style. Rome is a very working class, provencial city. There is nothing wrong with that. It's just that fashion or style is not what they lead with here. The tailored dapper men do exist here, of course, it just that per le persone per strada, you don't see it as much. Having said that, they still dress better than the men in America, anyday.

If you want an overall idea of how men in the street dress in italy, there is a guy who does quick street interviews with random people in diverse cities. The interviews are not about fashion - he is usually just asking what you do for work, how much do you pay for rent, how is the most famous person you ever met, what is the most you've paid for a pair of shoes, etc.. They are in Italian, of course, but you can take note of the men. He will usually say what city he is in. His name is @riccardosegna on Insta. I follow him to try and improve my Italian.

There’s a middle way. You don’t have to dress in stylish, slim-fit clothes. If you dress like Al Bundy in the 80s you look presentable enough as a man.

R31 That's true about Rome.

Milan and Florence are Italy's capitals of men's fashion. Milan has the shows. Florence has its Pitti Immagine Uomo fashion week.

And Milan is a design city so it just attracts lots of fashion conscious people.

R31 I understand your point of view. I will say I have catholic tastes so "working class" men can be dressed and groomed very stylishly.

Yes, R35, I am sure they clean up well. But for the most part Romans aren't concerned with style. They have it better than Americans, intuitively, but even they will admit, as I have been told by them, that Northern Italy is the style center of the country. Romans take pride in other things - like their amazing rich unparalleled history - which in the long run is more important and has served them well over 2,000 years.

The gays in Rome are interesting too. They are either in hiding or walking down the street in mascara with a fan. Romans tend to be more comfortable when they can spot their gays. But go to the Zara in Milan by the Duomo on a Sunday and your heart will skip many beats. The men are beautiful though. I will not take that away from them. If it's not their face, it's their hair, if it's not that it's their voice or how they dress. The guy who lives above me is a young dad who is the best looking, but his voice makes the ceiling rumble. I love to hear him plodding about. And the boys are very cute, like the high school crushes of your dreams. As an old man it makes me feel dirty, but I enjoy look at their faces, and their very 1980's "bad boy" attitudes.

^who ISN'T the best looking...

When you still live at home with your parents, it leaves you with a lot of disposable income for stylish clothes.

Bellissimo!