If you follow us, or any menswear blogs/Instagram accounts, you may have seen a recent influx in bold menswear looks set in front of the background of the beautiful Florence, Italy. This is no coincidence.

Tuesday marked the beginning of the 90th installment of the bi-annual men’s fashion event, Pitti Uomo. Gents from all around the globe gather to flaunt their personal styles at what has been called the most important menswear trade show.


We’ve put together some of our favorite looks from this year’s Pitti Uomo. Check out the outfits below, then show us what you’d wear to Pitti Uomo using #GentlemansBox

These gents know how to rock a good fedora. They don’t look cheesy or out-of-place because they kept it simple with crisp white hats that complement their attire. Even though there are a few different outfits in this image, the standout is that even with the bold colors and patterns their looks still appear effortless.

Another fedora and another bold look. We want to pay homage to all the accessories this guy fit into this look. Not only does he have the standard tie and pocket square combo going on, but also a few beaded bracelets, a couple of decorative rings, some stylish shades, a statement wallet, and even a savvy

At Pitti, it’s important to have a highly curated crew. If you’re going to be snapped walking the streets with a pack, you better be sure your outfits are color coordinated. These guys stuck to tans, browns, and reds to make sure they made for a pretty picture as they sauntered from tent to tent.

A photo posted by Plaza Uomo (@plazauomo) on

Intentional style choice or did this gent get caught walking out of a pizzeria with his tie still tucked? Our bet is on the former. There’s no time for style mistakes at Pitti.

Stand out from the crowd by experimenting with bold colors and materials. While this gent is more than likely pretty comfortable in more obscure attire, we still commend his no-sock suede loafer look paired perfectly with his powder blue suit and complementary orange pocket square.  

Pairing earth tones and incorporating some classic leather pieces like this small Louis Vuitton bag makes this look appear casual but still high end. Plus, if you can pull off a pair of round shades like this guy, you belong at Pitti.


Lest not forget about the ever-important #shoegame. There was no lack of strong shoe looks at this summer installment of Pitti Uomo. Whether we’re talking loafers, wingtips, or designer sneakers, the men of Pitti Uomo certainly did not fall short when it came to the pieces on their feet.      

This gent brought a pop of color to his Pitti getup with mustard yellow sunglasses in a classic and trendy shape, as well as a deep plum lined pocket square that complimented this stellar summer look.


Proof that true style defies the test of time. These guys are decked out in subtle accessories like sunnies and wallet chains. Bold blues were a commonplace at Pitti, and these gents did it right.      

If there’s one lesson to be learned from the collection of stylish men at Pitti Uomo, it’s not to fear prints, patterns, or accessories. Pile on the pieces from suspenders to ties, pocket squares to pinky rings, when expressing your personal style you can’t go wrong.