**Added/updated May 15, 2018…Addendum: Pros and Cons of Living in Milano and then Returning to the US**
I’ve been asked the same question a couple of times now. “Are you happier now that you live in Milan?”
Its a tough one to answer, because here, I find a different version of happy—or unhappy on a glass half empty day. The conditions have shifted, encompassing both improvement and downgrade.
I am certainly more stimulated every day, from the pedestrian level at which I now live. My street is particularly colorful, as apparently the last holdout of what the Navigli neighborhood once was (a public housing mess). It is actually a lot like Ybor City, with an even stronger latino bent. There’s a strip club AND a Peruvian restaurant downstairs.

Colonne di San Lorenzo, along the #3 tram line
I miss my car sometimes, but considering public transit is so good, it’s more of a style and comfort choice than one of convenience to own a car here. Transit isn’t without its headaches, but generally it functions reliably and the various layers from underground to street trams and buses makes connecting easy. This is one of the city’s greatest strengths.
Milano is simultaneously an exciting global city and a sleepy provincial village. It has name brand appeal and of course the filter of fashion. From outside, Milano looks glamorous. In reality, living here feels like being in a city of many villages, with a distinctively “small town” feel outside the city center.

Via Archimede
I suspect this isn’t helped by the conservatism of the Milanese. I noticed it most blatantly when I began wearing my purple tights to and from the gym. The looks I got from men and women, of all ages, would imply I’d tattooed Italian expletives on my calves! In general, people here care little about subtlety when they size up your outfit and express approval or disapproval.
Part of this may be the high number of elderly Italians, who balance the younger population more so than they do in the States…or maybe here they’re more independent and visible into old age.

Fabulous car spotting along Via Montenapoleone, like this 1960s era Mercedes Benz 280SE 3.5 Cabriolet
In any case, I find it all hypocritical, given most of them, from young to old, wear sleeping bags with sleeves (a.k.a. puffy jackets) as soon as the weather drops below 60. The likes of Moncler, Herno, and all their iterative knockoffs are the most unbecoming of winter wear I can imagine. Skiing is the exception, where efficient warmth is more important than style. But guess what you can’t do in central Milan?……..(side note it did snow last night but everything is melted this morning)

Puffy jackets and sweat pants………..
And though I am no flamboyant dresser, I don’t cling to black as if it is the only acceptable shade, so my speckled tweed coat and claret parka stick out wherever I wear them.

A supreme find! Suitsupply irish tweed double-breast winter coat
This is unlike the way I perceive New York or London, both of which celebrate the strange and embrace the adventurous. It’s also at odds with the idea of this as a fashion capital, where concepts and looks are born. Rather than a spectrum, there are two distinct style camps in Milano.
On one side, classical Italian tailoring and sartorialism, a la Brioni and Canali, make men look timelessly Bond-esque. On the other side, a “tribe” that is driven by obscure trends, hip hop cues (Yeezy), and rapidly shifting coolness, from exaggerated proportions (structured neoprene sweatshirts), to obscure mummy-like wrappings, to designers who’ve barely left the womb in Japan or Korea before they are “it.”

the queue outside Antonioli when they released Yeezy Season 1. Shaking my head.
Top it all off with a flat-brim cap! <sigh>

The Duomo on a clear fall day
There’s nothing wrong with either of these styles, as I find myself picking bits from both to experiment with. But nothing in the middle? I feel silly stepping fully into either of these extremes.
Curiously, everyday Italians don’t dress all that well. There may be a higher base from which all start, like better-tailored denim, but otherwise, the choices on the high street and in mainstream retailers is about the same as it is everywhere in the world. And all made in cheap labor countries. Sad, I know.
So it’s been a bit of a disappointment. Maybe my expectations were too high.

This is the best-dressed person I have ever seen in Milan, or at the least, on the tram.

One of my favorite spots for a chic lunch – Chic & Go Panini stand on Via Bigli

The bresaola, goat cheese, olive oil, and lemon juice is pretty awesome
What I am less forgiving of is the bizarre behavior of sales associates in Milanese boutiques.
Either they are overbearing shadows, which feels more like suspicion than service, or they could care less. If you need assistance, have questions, or would like another size, you make the first move. After so many awkward, uncomfortable experiences, I’ve had it. I will shop online!
Someone did tell me that my experience is a byproduct of a larger cultural mismatch. Italians are direct and take no issue asking questions, interrupting, etc. If they have a problem, they’ll tell you. As an American, this comes off as rude.

Etro headquarters on Via Spartaco…swoon!
Americans (and others maybe, I dunno) are likely to be more coy. They need a bit of warming up. If they’re irritated or feel snubbed, they’ll report to management or customer service after the fact. Thus, Italian salespeople overcompensate and feel a bit on edge around Yankees, not sure how to approach them. I suppose this is plausible.
Alternatively, they just resent Americans, so we get the cold shoulder period.

Somewhere near Porta Venezia with a classic bug in the foreground
To that point, let’s discuss the language barrier. Of course I make an effort to speak Italian. And I’m greeted one of two ways: with a quizzical look (of non comprehension), to which I have to reply with “Scusa, parla Inglese?” OR, I ask up front, and instead of saying yes, the waiter/sales associate/postal worker just says “how can I help you,” barely concealing their disdain. I swear a couple have rolled their eyes!
Now I respect that I am in Italy, asking natives to speak English. But I don’t go around assuming people speak English, using it straight off, like some of my classmates do. It would be nice to get some credit for at least trying and smiling. Check back in a few months, and this may be a moot point as I become more fluent.

A magical thanksgiving dinner with other ex-pats and new friends
OK, only two more gripes, and I’ll make them quick, then on to the awesome parts of living in Milano!
When you visit Italy, Spain, or other mediterranean countries on vacation, the custom of shops and restaurants closing for a few hours in the afternoon, from about 2pm to 4pm, is probably charming. Yay nap-time! When you live with it, it’s infuriating. The attitude toward convenience is essentially nonexistent.
Want a take-away coffee? No. Want to pay for your dry cleaning with plastic? No. Want your wifi setup in less than two weeks? No. You get the idea.

Swooning over Italian fire trucks. They’re not as loud or large as American ones, but then again, what would you expect? The fire station is just down the street from me, a coincidence I swear!
Italians use cash and coins far more than anywhere I have ever lived. Baristas, proprietors, and even corporate store managers (like for my mobile carrier) groan when you want to use debit for less than €5, but if you present them with a €50 note, you get a similar reaction. Okay…so…I should always have coins and 5- and 10-euro notes? That’s logical, especially when your bank’s ATMs are regularly out of service…
Oh, and you can’t pay for postage with a card. I learned this the hard way by buying €60 worth of stamps and then having to run to the bank after a broken conversation in English and Italian.
Strangely, online banking is super simple. I pay my rent each month with just a few clicks. (silver lining)

Speaking of stamps. Mail from The Paper Seahorse!
What else?
My last major let-down has been the dating scene. First, all the walking dreams you see on the street? Yeah, they’re all straight. Ridiculously metrosexual, with their man bags and kissing their mates’ cheeks, but totally heterosexual. (sidebar upside: many of them are very comfortable with their sexuality and make excellent friends if you can manage to not fall in love)
And the gays? Well, they’re not drastically better than anywhere else. They separate themselves into their own enclaves and hangouts, have mostly terrible conversational skills, are cliquey, and have all slept with each other. Sound familiar?

Shopping with Italians at Suitsupply
I have been on some fine dates, with nice people. But nothing mind-blowing. Milan has the same affliction of other metros. Everyone is busy chasing their careers, degrees, and achievements, so clubbing on the weekend and going home with someone random is the simplest path to intimacy and sex. OR, guys meet online, but only want the transaction of sex, not a conversation or a coffee. Just an orgasm and get out.
So there it is. Life ain’t all that rosy over here.

Amazing, charming old school paper store I was recommended to behind the Galleria
What I do like about Milano: the architecture and cityscape is unique and pleasing. More influenced by Austria, Germany, Switzerland, and France than the rest of Italy; much was rebuilt after the war in the modern, deco, or even brutalist methods, all of which I think are fascinating.

Pizza at Premiata on Navigli Grande
It is hard to eat a terrible meal here. I’m sure they exist, but eating out isn’t usually cheap, and you get what you pay for, with delicious pasta, pizza, fish, cured meats, cheeses, and of course, amazing desserts.
I reserve approval for dinner options that are quick and/or healthy, as they do not exist.

Shrimp (gamberi), goat cheese, and avocado pizza

Squid-ink dough pizza with…some other deliciousness

Vegan pizza that was also delightful

The Galleria never disappoints
I have met some lovely friends, busy as they are. Fellow ex-pats Andrew and Patrick are both aesthetes with taste and creativity I can only dream of, and they have warmly welcomed me to a few dinners, for thanksgiving, and for a christmas party.
And, I really, truly, love my (100) classmates. I don’t party with them much, because I’m not much of a partier period, but to pass time with, over assignments, commiserate, and learn from, they are pretty awesome. Of course I’d love if they were all gay, because a lot of them are cute, but alas…
They are from all over the globe, from every imaginable background and all with a story. Somewhat self-selecting, it would be hard to move thousands of miles for grad school and not have a good motivation. It’s a bit like adult summer camp.

Castro the chill kitty in my building. Elevator attendant too.
I have a nice flat that I feel very comfortable in, and though I miss all the comforts, I have plenty here (and few hardships). No complaints!
I would be remiss to not mention the general proximity to the brands I have loved for so long. Every Italian designer or label has a presence in Milan, either with stores, as stock in multi-brand boutiques, or with private showrooms. And there is no shortage of places to consult a trained tailor for a bespoke suit (or any iteration of the process, from fully bespoke to made-to-measure to simply adjusted off the rack).
PLus, boo-coo outlets, consignment stores, vintage, and other treasure hunting that you can’t get outside of major fashion centers.

Glittery holiday tram!!
And just today, I visited the Museo del Novecento for free (first Sunday of each month). It is one of Milan’s many centers of visual culture, encompassing everything from The Last Supper (circa 1494) to brand new works. I’ve already been to Armani/Silos and Fondazione Prada. Next stops: Casa Boschi-Di Stefano and Villa Necchi (where I Am Love was filmed).
So there it is. Pros and cons. Gripes and new obsessions. Ups and downs, like anywhere and everywhere. Now I know what it’s like to move. And I’ll want to do it again I’m sure. Goldilocks isn’t satisfied quite yet.

Museo Novecento view of the Duomo
3 comments
very good
Hi Alex T. I know this is an older post, but for me it reads like a fresh slice of pizza hot from the oven with artisanal mozzarella, fresh tomatoes, etc. It answers a lot of questions for me. It’s a dream to live in Italy (about sixteen different places-seaside, mountaintop, city, village, northern, southern) for at least a year. I am going to check the archive to see if you wrote a post about moving to Italy. Thank you. TED talk.
Thanks Albert, for the nice comment. I hope you’re enjoying your time in Italy!