Pitti Looks From Afar: Tailoring Should Be Fun

There are two times of year that I look forward to more than others: January and June. During thee months, the biannual men’s style trade show, Pitti Uomo, happens in Florence. Though I haven’t lived out my fantasy of attending yet, I’ve long admired the men’s looks from afar.

No, I’m not talking about the preening peacocks that dominate the Florentine streets. I’m talking about the men who know how to have fun with clothing. What’s the difference? Fun is expressing yourself by breaking the rules after you’ve learned them, in a way authentic to oneself. Many men who’d fancy themselves Pitti street style stars haven’t learned the rules in the first place, and receive attention because their sharp-fitting jackets and colorful trousers appear novel in a sea of navy, gray, brown, and cream. Wearing classic colors, however, doesn’t signify a lack of fun. Rather, it’s a reminder that the fun in dressing happens in the details that many people don’t notice upon first glance.

Many street and social media photographers, however, take highly stylized photos that don’t accurately capture details and the essence of occasion. They’re edited to perfection, and while I’m a firm believer in crisp, clean photos, the best men’s shots have a spontaneous appearance and an unedited quality that signifies both the subject and shooter aren’t trying too hard. They’re in Florence, after all, so not practicing the art of sprezzatura is brutta figura.

One Instagram that captures distinct style during the Pitti seasons is run by Greg Lellouche, the founder of online clothing shop No Man Walks Alone. His @pittilooks feed features the sort of unedited images of real men—and women!—wearing everyday pieces with ease, insouciance, and individuality. Lellouche focuses on details, too, and takes several shots of each subject, emphasizing their shoes, jackets, trousers, and accessories. The account’s first look from Pitti 94 is of Joe from Seoul (there are no other details about his identity), wearing a notch-lapel navy suit, a crisp white dress shirt with a formidable collar, a silk repp tie in chocolate brown, beige, and royal blue, a turquoise ring, and a white Panama hat. Joe’s look is a reminder that details, fit, and quality matter. While navy suits pass muster in most occasions, they take on a life of their own when made with care and accessorized with character. Joe’s look is also fun and elegant enough that it’s convinced me, a firm opponent of brimmed hats on men under 28, that I want a Panama hat this summer, whenever I can afford one.

Always elegant is Domenico Gianfrate, the tattooed impresario behind his eponymous label. The quintessential Italian silver fox, Gianfrate favors elegant monochrome outfits that dip into fashion yet exude personal style. His latest debut, captured by @thesartorialist, is a khaki-on-khaki masterpiece in slightly varying shades. Gianfrate’s shirt is a hue lighter than his trousers, and is a rugged yet playful military-inspired rendition of the band collar. With single pleats and side buttons instead of belt loops, Gianfrate’s trousers cut a dashing figure that makes his ruggedness look sophisticated and dressed up, despite the absence of a jacket. Hopefully this latter trend continues, because belts are looking long in the tooth these days, especially when worn with tailoring.

Though Pitti peacocking has died down, some men—men of excellent style, even—parade around in questionable outfits. This year, there were a surprising number of gents sporting shirt collars layered over suit or jacket lapels. Not even Sebastiano Guardi, one of the dapper reprobate brothers behind Italian shoemaker Barbanera, was immune to this trend, wearing his beautiful white double-breasted suit with a diamond pattern camp-collar shirt from the brand’s new ready-to-wear line. The shirt on its own is a winner, though obscures the top of the lapel in a manner that dominates it. We’re no longer in the 1970s, and Burt Reynolds isn’t a style icon, so this trend should go back to where it belongs—the past. Kudos to Guardi for daring to try it, for the true man of style knows that the only way to eventually get it right is, as the late, great Glenn O’Brien called it, “Getting it perfectly wrong.”

Where Guardi made a white jacket misstep, Mark Cho of The Armoury and Drake’s nailed it. Despite their history as a key garment in evening wear, white and cream jackets translate better in in theory than in practice when incorporated into daily wardrobes. Their brightness risks drowning out the rest of the outfit, and Cho’s decision to pair his off-white Liverano & Liverano jacket with a bespoke teal shirt in a beautiful foulard print (likely from a vintage bolt) and navy trousers balanced out the spots of attention. In tieless outfits like Cho’s, shirts can speak louder than when neckwear is involved, since it becomes the ensemble’s focal point. Subdued foulards are also a great way for pattern-wary men—stripes and plaids notwithstanding—to try shirting with more verve.

The Armoury and Drake’s, more than any other modern tailoring purveyors, remind dressers that verve is essential in pushing the boundaries. Take Michael Hill, creative director of Drake’s, who’s a master at this. In one Pitti snap, Hill is caught wearing a classic navy suit and a crisp white pocket square. The details, however, are where Hill has fun. His suit is cotton—not wool—a fabric Hill loves for the reasons people hate it (it wrinkles). His navy tie with thin yellow horizontal stripes flies in the wind, set against a white shirt with red candy cane stripes (hopefully a piece from an upcoming Drake’s collection). Topped off with a rounded interpretation of the classic tortoiseshell Wayfarer and a winning smile, Hill’s outfit exudes personal style in all the right places, meanwhile acknowledging and tweaking classic standards of decorum. The elated expression on Hill’s face communicates that “It’s the 21st century, chaps. Tailoring is fun, so don’t take it so seriously.”

Beyond the boundary pushing, Pitti also serves as a reminder—in case we’ve forgotten—of what is distinct and enjoyable. Tobacco suits. Loafers sans socks (or with no-show socks). Baudoin and Lange, the English maker of comfortable Belgian shoes. White trousers. Bags (I’m convinced The Armoury crew would perform a citizen’s arrest if they spotted a backpack at Pitti). Ring Jacket. Drake’s. Aperol spritzes. Florentine trattorias. Repp ties. Double breasted ensembles (or one-and-a-half breasted ensembles, if you’re employed by Brunello Cucinelli). Smiles. Elegance. Grace. All exquisite pleasures, all small luxuries, some more attainable every day than others (smiling is a lot more affordable than spending $3,000 on a suit), yet all are reminders of the importance of details, extra consideration, the long view, and joy.

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Pitti Looks From Afar: Tailoring Should Be Fun