The last year of my life led up to this one seismic life change: moving to Sicily to get my Italian citizenship by descent—and staying there.
Eight months of collecting vital documents spanning decades. Researching every part of the application process. I even represented myself in a court case against the Illinois Department of Public Health to rectify name discrepancies. I look back and wonder how I did it all by myself when some people pay thousands to offload the work to a specialized agency.
I quit my cushy fashion job in New York City, liquidated most of my worldly possessions, and after some bitter goodbyes, now I’m here. And I couldn’t be more stoked.
Well, I find myself trying to MacGyver outfits from what I thought was a fierce artillery of style.
Maybe part of that research could have included Sicilian fashion norms, as I’m not in a metropolitan area where my American city-boy style could blend in among the rest of the trendy socialites.
I didn’t forget the obvious things like swim trunks, dress shirts, and shorts, but I would shuffle the composition of my suitcases if I could go back.
If you’re planning a trip to Spain, Italy, Greece, or the southern coast of France and looking like a stereotypical tourist isn’t part of your itinerary, here are some things I’d be sure to include.
A Chic Bathing Suit
One trip to the beach is enough to realize that Europe does swim gear differently.
Men young and old rock the banana hammock, and frankly, I’m considering it too. There’s nothing more liberating than owning a look, and in this case, the perfect tan that comes along with it.
But I understand the majority of my American brethren aren’t ready for that. I do, however, recommend something with a 5” inseam. Board shorts that fall below the knees are a dead giveaway of an out-of-towner.
Mine is the product of a collaboration between Le Alfré, a brand we’ve covered before. The print, fabric, and dimensions are nothing less than Positano-worthy.
Linen Pants
Being pro-linen for a European summer is by no means a controversial position.
I had some linen shirts, and just before I left, I decided, eh, might as well scoop some matching bottoms too. Thank goodness I did.
In my arrogance, I totally thought a loose-fitting pair of 12oz denim would suffice. Temperatures in Sicily have hung around 92℉ during the day without skipping a beat. These linen pants came to the rescue once I met some locals who invited me to some snazzy get-togethers where shorts simply wouldn’t match their stylish, Italian aura.
I avoid purchasing clothing on Amazon 99% of the time (especially from those made-up brands with weird names), but I was short on time ahead of my departure. In short, best ~$35 ever spent.
More Plain Tees
If I’m not wearing a dressy button-up I’m in a tee shirt—especially in this heat.
Between all of the tees I brought with me, only 30% of them are completely plain.
Whether the front has a band logo or a neat graphic from a brand, I like my graphic tees. But for guys over the age of 25, they’re not as common as I thought.
That Rose Bowl championship tee might as well say “I AM FROM AMERICA” with a bald eagle soaring over the text. My Reigning Champ tees are going to hold it down until I can find shirts of comparable quality.
Dressy Sandals
If there’s one thing I’m relieved to have squeezed into my suitcase, it’s my pair of huarache loafers from Knickerbocker.
Why, you might ask? Tennis shoes and leather sneakers can’t keep up with the heat I’m in right now, and you’ll be faced with the same oppressive rays unless you’re coming in the off season. Tennis shoes aren’t common for casual wear, anyway.
I’ve seen plenty of flip flops at the beach, but those don’t fly at the nightclubs. Huaraches, fisherman, and gladiator sandals are up to code, both airflow and style wise.
More Natural Fabrics
Stepping off the plane was like the classic western movie trope: cowboy protagonist winces as the sun beats down overhead, a hawk screeches, and a dramatic harmonica riff ensues.
Have I mentioned how hot it is here?
The difference between fabrics like cotton, linen, and hemp vs anything synthetic is night-and-day. A polyester shirt will radiate BO before you close the door behind you, and once you’ve built up a proper sweat, cling to your frame like static.
Classic Frames
Classic sunglass frames are another list item that has less to do with utility and more to do with integrating the local way of dress into your own.
If you’re kitesurfing in A Coruña, rock your wrap-around sport shades. I’d look like the PC Principal if I wore them to a vineyard in Abruzzo. And by that I mean hilariously out of place.
I treated myself to a pair of tortoise-shell oval frames from this Italian brand Bust Out Eyewear. The optical store I scooped them from even let me pick out custom lenses on the house, and I couldn’t say no to these green gradient lenses—elevated yet traditional.
Uber-sporty shades are dope. Don’t get it twisted. But some of them look like a Spartan HUD, and that look is best kept where the activity is just as high octane as killing the flood in Halo.
There’s nothing wrong with being a tourist. In fact, some of the most wholesome interactions I’ve ever had were with people visiting the United States for the first time. Not once did I make any internal remarks about their outfit.
But there’s a certain amount of relief one gets from blending in. This list isn’t about suppressing your roots. Think of it as a pocket guide to sipping, sunning, and swimming in style.
With that, I leave you to stuff your luggage. Arrivederci!
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