Why Do Men Want to Dress Like an Italian?
(or is it the lifestyle they're after?)
A few weeks back, I mentioned this debate shortly in an Instagram story (during peak season Stealth Wealth / Old Money): “Is it really the clothing style that appeals to us so much (as far as I'm concerned, old money is pretty boring and... old?) or is everything that revolves around the clothing style actually what appeals to us most?” Is it the bag of money in the back of your Ford Mustang? The idea of having a Rolex on your arm one day (or an entire vintage collection somewhere in your marble-clad home) and having a top-to-toe groomed (often blonde) woman on your arm with the body of a top model and the face of a 20-year-old? Who knows.
As far as I know, dressing like an Italian has been a thing for ages. And trust me, I understand entirely. If I were born as a man, I’d probably not step out of the house unless I’m head-to-toe dressed in Italian Sprezzatura style (insert pinching hand emoji here). While I’m all up for the Italian allure, something in me says I could raise a similar debate as I did about the Old Money equivalent. Because what is the Italian way of life, and what makes its way of dressing so attractive?
Your typical Italian: charming, confident, and well-dressed
Visit any menswear blog, news outlet, or other media type, and there’s a 99% chance of finding content on the well-known Italian style. Even when you’re not into style or menswear at all, I’m sure you can paint the picture of the typical Italian guy.
He’s dressed well (of course), wearing some casual tailoring that fits him like a glove, often paired up with some slightly unbuttoned shirt underneath his linen (but not crinkled?) blazer. Holding a cigar(ette) in his right hand, mid-length messy hair, a pair of loafers or other semi-open shoes, and striking sunglasses, he’s probably engaging in a conversation with his friend (dressed as good or even better), making *the* hand gestures. And we love it.
The Italian way
But is it really solely the clothes? If you ask me, the answer to this will be a hard no. It’s the allure, the je-ne-sais-quoi mindset, like the French master so well in their way. While I think the Italian man is born with the imprint of this reputation to uphold, I believe it’s in their blood.
Of course, you are that man with charisma who knows how to dress every day, no matter what is on today’s agenda. And you also have time to enjoy an extended lunch where the wine flows profusely - to simply return to your creative job afterward (and turn some heads on the way there). It’s merely another approach or version of the lives we all live every day.
While you could classify this as a case of ‘the grass is always greener,’ I think the Italian way of life should be celebrated. It is one of the best sources of inspiration - it goes as far as clothing, grooming, self-care, being confident, and doing what you enjoy in life.
More than a dress code
Let’s face it. If we see the big picture, what these handsome Italians wear is only a tiny part of how they come across. Clothes aren’t enough to cover the load. So what exactly are the nuances that elevate their outfits to an exceptional level? I think it’s this: it’s being a man, not ashamed of spending time on your appearance. It's allowing yourself to buy and wear clothes that make you feel good. It’s paying attention to the details, knowing what works for you.
It’s acknowledging that dressing well is much more than buying a random set of beautiful garments. It is wearing and purchasing beautiful garments that fit your lifestyle, aesthetic preferences, and how you look at life. And styling all of this together is what achieves that sought-after splash of confidence that seems to make the Italian man.
But, seriously: how to dress like an Italian?
Are you still here to find out how to at least dress in the Italian Sprezzatura style (the art of effortlessness)? I got you. Read on to find out how to achieve the signature Italian look that comes across as both casual and artfully sophisticated, even if you’re not a born Italian.
Embrace (casual) tailoring
Your typical Italian style icon probably won’t leave the house without at least one dressy item. Be it a tailored blazer, a pair of dressy loafers, or a business shirt: you’d better add these to your shopping list. Combining formal items with more laid-back and casual garments is what creates the perfect harmony in a daily outfit.
If you’re not into a formal aesthetic, opting for casual tailoring is probably more for you. So, for example, a casual blazer - unlined or deconstructed - or opt for the cotton version of pleat-front trousers. Your suit separates are winners as long as you don’t compromise quality. Good tailoring should always be non-negotiable. Experiment with a printed jacket and plain trousers.
Go neutral or tonal
Some of you may know I’m a sucker for tonal dressing, aka monochrome looks. And for a fact, Italians do love this technique too. Whether you’re choosing a neutral color palette throughout or building the base layer of your outfit in monochrome tones with an added pop of color (like moss green, for example), both are Italian-Style-approved.
This isn’t a cue to slap on all items you have in navy blue without considering their individual specs - pay attention to proportion, silhouette, and, crucial: texture. Literally, any outfit lights up when two or more different textures are incorporated.
Know how to accessorize
Yes, a good watch does the trick to come across as well-groomed. But the smallest details make the difference. That unique ring, colorful bracelet, or original tote bag you brought back from your trip to Mexico matters and adds that unique, personal touch. Or fully on-trend now: the bandana or a pair of colorful spectacles. But balance is essential.
A new take on knitwear
The knit polo seems to be increasing in popularity by the minute. It’s the ideal item all year round and an easy instrument to add some of that texture that I just talked about. Go button-through for a more relaxed approach, or experiment with crochet if you’re an avid admirer of current menswear trends. What truly does the Italian trick for me is a soft and elegant mix of silk and cotton, for example.
Don’t take rules too seriously (no one likes them anyway)
How do Italian gents seem to look so put together but so relaxed at the same time? Not taking style rules too seriously (something that’s right up my alley). Wearing a casual suit combination doesn’t mean you need to tie the knot (literally) - skip the tie. And even better: unbutton your dress shirt's first two or three buttons. Want more comfort? Why not add a retro sneaker? Your go-to, if you want to learn from the best, is, without a doubt, Mr. Alessandro Squarzi.
Want to dress like an Italian but have no idea where to start?
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