The 10 Best, Most Double Tap-Worthy Street Style Looks at Pitti Uomo 93

Twice a year, men of all ages, ethnicities, and sartorial tastes gather in Italy’s historic city of Florence to attend the world-famous menswear trade show, Pitti Uomo. The 93rd edition of the trade show promised attendees and fans all they could ask for — from the dandies that turned up in overly colourful, lavish, and costume-y outfits (otherwise known as “Pitti peacocks”) to the men that, thanks to social media and fashion blogs, have massive online menswear followings, the latest Pitti had everything.

Short of actually being inside the walls of Fortezza de Basso, the best (and worst) reflections of the street style worn by patrons, guests, and designers at Pitti can be found on Instagram. With photos from Milan Men’s Fashion Week now flooding our timelines, we’d like to say goodbye to Pitti 93 with a compilation of the ‘fits we double tapped for the hardest on Insta this past week.

PITTI Immagine Uomo 93 – day 1

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Menswear is full of rules and once you fully understand why they exist, one of the most fun things you can do is break them. Mixing formal — this double breasted, thick wool suit — with casual — this classic leather bomber with shearling lining —  could easily result in a high/low clash, but this gent pulls it off expertly. What’s more, the tone of brown found on the suit and the jacket are almost identical, but the outfit is broken up by the stark contrast of the shearling lining inside the bomber offers, which makes everything work without being too match-matchy.

Mixing casual with casual, this shot has been dubbed “slightly hungover, middle-aged Dad, pre-espresso,” which is a look I can only aspire to. Vintage military threads have been a trend that’s picked up quite a bit of momentum over the past few years, which has been great whether you’re interested in finding classically cut, authentically aged fabrics with history to them, or you’re just starting to realize your (ironic) inner-allegiance to the Axis. But this simple and muted USMC workwear jacket pairs very naturally with some faded indigo denim and a worn-in canvas tote bag. I like this because, all together, this says “Just because I have a two-month-old that keeps me up all night doesn’t mean I can’t be a cool Dad and go to Pitti.” You go, cool Dad.

Here, Alessandro Agazzi of Simeone Napoli continues this year’s workwear trend at Pitti by wearing the iconic Red Wing Rover boots. Mid-brown cords and an Aran knit sweater are classic winter casual go-tos, but Agazzi ups the formality and adds some structure to his ‘fit with the wool trench coat. Something can be said for the practicality and versatility of this, as it looks equally at home within the walls of one of menswear’s biggest events of the year as it would if the Italian wore it reeling in crab nets on the deck of a Maine fishing boat.

Speaking of fishermen, Carlos Castillo of Spanish brand MAN 1924 has a beard most anglers would be jealous of. If Castillo can fish anything like he can dress, he’d be bringing home the big tuna, as here he exemplifies how to dress down a suit like a pro. Tweed is a winter suiting staple; not much keeps you as warm as an authentic Harris tweed suit, so Carlos can afford to wear his overtop a simple white T-shirt. If it gets a little nippier out, he can always pop on that sweater he’s wrapped casually around his waist for an extra layer, but it might just be there because he ripped his pants earlier in the day. The expressions of the two gents behind him have me thinking it’s a possibility.

“Don’t eat cheese before bed,” “no white after Labour Day,” and “if you do that you’ll go blind and grow hair on your palms” are all grade-A examples of fake news. If you need proof of why you shouldn’t let a date on the calendar decide what colours you’re allowed to wear, just look to menswear God and Pitti Uomo celebrity, Alessandro Squarzi. White pants in the winter is a Squarzi signature, and you really can’t argue with the guy here. Worn with brown suede lace-up Alden boots and a green corduroy topcoat, Mr. Squarzi brings enough winter to the palate for this not to look any bit out of season.

Jorge Navares, also of MAN 1924 and the proud owner of a Hemingway-esque beard, is brother to Carlos Castillo and fellow white trouser enthusiast to Alessandro Squarzi. With two such convincing examples of wearing white after Labour Day, any remaining doubt has to be cast aside by now. Navares also draws parallels to Alessandro Agazzi’s workwear theme by wearing Red Wing Classic Mocs, and rounds off the muted tone of the outfit with the hooded gaberdine rain coat.

It might actually impossible for you to read a single Pitti Uomo or #menswear article without the mention of the Italian word “Sprezzatura,” which has been so overused it’s pretty much a meme now. However, if this is your first time hearing about the sprezz, the loose meaning behind it means something along the lines of a studied or artful carelessness. It’s used in menswear all the time to describe an outfit that looks awesome because it’s not been fussed around with too much — perfection through imperfection, if you will. Scandinavian men’s style icon Konrad Olsson personifies #sprezz here, with his tweed topcoat thrown overtop his shoulders, lapels slightly popped, gloves stuffed into his breast pocket, and casual black tee untucked from his grey trousers. Olsson kept it simple and killed it on day two of Pitti Uomo.

Also keeping it simple was Maxim Lundh, showing us that sometimes all you need is a kick-ass piece of outerwear to look well put together. The double breasted, dark grey houndstooth overcoat is toned way down in formality by the casual, sloping shoulders that come with having a raglan sleeve. The popped collar and undone belt drop the formality level even lower while steez levels rise — this isn’t Mr. Lundh’s first Pitti.

Certainly a step up in the level of formality, Insta model Raphaël Simacourbe dons the full grey flannel suit. By keeping the topcoat in the same colour family, Raphaël runs the risk of looking washed out, especially given the season and his cobblestoned surroundings. But the key to a good monochromatic ‘fit is picking slightly different tones and fabrics that contrast with each other so that it still comes off as interesting. Reaching for a darker shade of grey and softer fabric in the topcoat keeps this looking compelling.

It just wouldn’t be Pitti without including some wack shit. But to be honest, the more I look at this Pierre-Louis Mascia, the more I admire him. Scratch what I said about that second picture, this is the level of sprezz I aspire to having when I’m older. While that torn-up scarf isn’t quite on the Lenny Kravitz-sized spectrum, it looks like it would keep me warm enough to meditate outside all day, which is probably what he comes to Pitti for. Seriously, this guy is so zen, I bet he’s not even sitting on that wall. I used to think socks with Birks was a bad idea, but Pierre’s reminding me of my own mantra: rules are meant to be broken. Used to think Steve McQueen was the king of cool? Just check out what his counterpart in Papillon, played by Dustin Hoffman, is rockin’ on his noggin. I’m not going to say it was Pierre Mascia inspired, but both of them share the name “Louis.” Coincidence? I don’t think so.