Pitti Uomo is a 4-day conference, though the fourth day is widely regarded as unnecessary by many who attend the show. Most of the action is on days 1-3, though brands who have booths set up are required to stay up on day 4 (at least half the day, it seemed). Nonetheless I still planned for and packed for four days of Pitti plus the additional time I had during my time in Italy.

Here is what I wore each day and how I might’ve done it differently.

Day 1: Naïveté

Shop this outfit: Tan linen/silk Spier & Mackay Neapolitan suit | Similar shirts: Spier & Mackay cotton-linen stripe shirt | Cavour linen blue stripe cutaway shirt | Similar tie: Blue basketweave tie | Shoes: Meermin polo suede penny loafers

I walked the 20 minutes or so from my apartment to the entrance of Pitti where the street style photographers all hang out to shoot people where they come in off the street. It was around 9:30am when I arrived. I ran into Luke Alland (@theexiledbrit), who I chatted with a little while I snapped photos of people coming in. It was already in the 90s Fahrenheit and the sun was brutal. After about 15-20 minutes of standing there, shooting and talking in the sun, I decided to head inside to gather my press credentials and cool down. Luke looked at me and said “oh dude your whole back is sweat through.”

“Ehh it’s fine,” I said. “You sure?” he warned. I went into the bathroom to check it out, and no it wasn’t :D. I had to take off my jacket and walk around for 45 minutes inside to let it dry out before I put it back on (and Philippe took the photo of me above).

After that morning experience, the rest of day I spent as much time inside and in the shade as I could.

Night 1: Go for Comfort

Shop this outfit: Tan linen/silk Spier & Mackay Neapolitan suit, jacket worn separately | Similar shirts: Spier & Mackay cotton-linen stripe shirt | Cavour linen blue stripe cutaway shirt | Similar pants: Todd Snyder cotton-linen 5 pocket | Sperry tan suede boat shoes

On night 1 was an event for Scarosso in Harry’s Bar The Garden, a pleasing courtyard space.

During the day I wore my polo suede Meermin penny loafers, which I was only able to wear because I bought some Pedag insoles for them that alleviated the heel issues I had with the shoes. However, they make the shoes a little tight, and so by the end of the day after walking I had to change shoes. So for comfort’s sake I put on my tan suede Sperry’s. Since I wouldn’t wear those with a suit, I also changed pants into my Billy Reid cotton-linen Ashland 5-pockets, and took off my tie.

Day 2: Color and Pattern

Shop this outfit: Solid green Suitsupply blazer (sorry this is an impossible jacket to find good matches for) | Similar shirt: Spier & Mackay cotton-linen stripe shirt | Spier & Mackay mid-blue cotton-linen trousers | Similar shoes: Alden snuff suede tassel loafer

I still wasn’t fazed by the heat on Wednesday, day 2, though maybe I should’ve been. On this day I wore my favorite reverse-stripe blue cotton-linen shirt from Proper Cloth, with my green windowpane wool-silk-linen Eidos blazer with blue cotton-linen trousers and suede tassel loafers. These are my most comfortable dress shoes and I wore them again every day after this.

In the morning, I was a little smarter and took off my jacket while I walked to Pitti from my apartment and when I camped out at the entrance to shoot photos. However, I learned a little later where the veteran photographers spent time—in the shade under the main building or elsewhere inside, rather than under the direct hot sunlight outside. I changed locations and joined them there from day 2 on.

I jumped in the pool over at the hotel Andreas and a bunch of the other guys were staying at that afternoon and it was a wonderful way to cool down.

Night 2: Double Parties and No Dinner

Shop this outfit: Proper Cloth Mayfair cream dinner jacket, white luxury broadcloth shirt and black cotton-linen trousers | Yanko black suede belgians from Skolyx

Pitti is awesome because you get to wear formalwear at the evening parties if you want to. I wanted to, and was very smitten with this Proper Cloth cream dinner jacket (those lapels are just about the perfect shape to my eye; nice work Chris Callis). They generously gave me this entire outfit (I bought the shoes and had the bow tie already). Funnily enough, three of us at Pitti all had this same dinner jacket—at least the same fabric. Nicke in the photo above is wearing his DB model and Andreas wore his the first night. Tonight’s parties were the WM Brown x EGM cigars party, and the Plaza Uomo party.

Anyway, this ensemble is great but I made some errors that I’d change if I could go back.

1. I went with cotton-linen trousers because I intended to wear it somewhat casually, open collar, no tie; and also I sort of had in my brain that it’d be nice to be able to wear these things with other outfits. But my logic broke down because doing black means I’m not going to wear these with any other outfits, and if I were going to get a pair of pants to wear specifically with a dinner jacket, why wouldn’t I get a legit pair of black tuxedo trousers, even ones made from linen like these, with a stripe down the side?

2. The shoes are suede, which again in my brain was for the casual way I intended to wear this. But again, being black, I won’t wear these with much else, so why wouldn’t I go with legit black tuxedo-appropriate shoes, like the patent opera pumps Nicke is wearing and which look much better? (Though now that I have these, they have me thinking about outfits I can create with black jeans).

3. I wore a normal white shirt with normal buttons, (not even double cuff). This isn’t actually something I regret, per se. I spent a lot of energy thinking about whether I wanted to commit to a tuxedo shirt with studs and all that that I’d only ever wear with this jacket. But then I found this photo of Humphrey Bogart in Casablanca and realized his shirt had normal buttons. And I learned from some old Apparel Arts illustrations that the nature of summer black tie with a cream dinner jacket lends itself specifically to a more casual take. So I am happy with the shirt I wore; but may at some point in the future invest in a tuxedo shirt (I’d do a bib, not pleated). Or maybe smarter, just a covered placket shirt.

So if I had to do it again, I’d either embrace the more casual idea and go with dark navy cotton-linen trousers and dark brown suede Belgians—both things I’d get some mileage out of and would therefore be more versatile in my closet; Or I’d embrace a legit black-tie ensemble and get patent shoes of some kind and get legit tuxedo trousers.

What’s nice is that I can easily fix these things going forward. If I get some dark navy trousers, I can wear those with this jacket and the black Belgians and it’ll look great. If I get a studded tuxedo shirt, I can wear with this exact fit and it will elevate it nicely.

Intermission: My Watch

Shop this watch: WatchShopping.com

I only took one watch, and it was the brand new Seamaster 300m I bought right before the trip from Topper Jewelers in California. I figured it’d wear well with everything I brought, and indeed it did. Maybe a tad chunky for the dinner jacket outfit, but judge for yourself in the photos above.

I put it on the flat link bracelet made by Uncle Seiko (thank you Larry). I like the somewhat old-school Omega diver vibe a flat link gives this watch. I also could not resize the OEM Omega bracelet on my own (the loctite on the link screws broke my small screwdriver, and there wasn’t anyone on duty at the Omega boutique locally when I dropped in the Friday before I left for the trip).

Day 3. Commitment to the Cause

Shop this look: Similar blue DB blazers: Spier & Mackay blue twill double breasted blazer | Spier & Mackay dark blue cootton-linen DB blazer | Similar trousers: Spier & Mackay cotton-linen trousers | Suitsupply cotton-linen trousers | Similar shoes: Alden snuff suede tassel loafer

I seriously debated wearing a jacket on day 3. But I committed to the cause because I looked at the rest of what I’d packed and realized if I changed my plans now, it’d be more annoying later.

This fit was great; when I took off my jacket, the fun horizontal-stripe shirt worn on its own looked cool with the white cotton-linen trousers I was wearing. But it also looked great under the jacket. So it was versatile. And I spent much more time under the shade this day.

Night 3. Quick Shirt Change

Nobody took a photo of me this night so I don’t have a pic of the outfit I wore at the Alexander Kraft Monte Carlo party at the Odeon Cinema. But I wore the same thing I wore during the day, and simply put on a white open-collar shirt. I don’t remember why I changed shirts—perhaps I’d gotten too hot during the day and needed something fresh. I did do a Reel with French Instagrammer Jamais Vulgaire which you can see here to see the very top of my jacket + shirt.

Day 4. Wandering Aimlessly

Shop this outfit: Similar navy blazers (lots more on my shop my closet page): Spier & Mackay full-canvas E. Thomas hopsack navy blazer | Saman Amel wool/silk/linen navy blazer | Navy one-piece-collar polo: G. Inglese | PML one-piece collar polo | Yeossal swallow polo | White jeans: Sid Mashburn natural jeans | Todd Snyder cotton-linen light gray five pockets | RRL white jeans | Polo Ralph Lauren white slim-straight jeans | Similar shoes: Alden snuff suede tassel loafer

Day 4, like I said, is the day many people leave, the booths tear down around noon, and Pitti is all but deserted.

I put on one of my favorite, go-to outfits: My favorite faded navy Eidos Lupo polo with my raw silk navy Eidos Tenero blazer, my favorite pair of off-white jeans from J.Crew, and my tassel loafers. Every item of clothing comes from 2014 or 2015, the loafers from 2018 or so.

I wandered around the fair, however, to chat with the bored booth attendants. Specifically I talked to Stile Latino, Saint James, and the Alden rep (see my videos / Reels on my Instagram for those videos).

Night 4. Romantic/Touristy Sunset Alone Overlooking Florence

I walked the mile or so up the steep hill to Piazzale Michaelangelo, a parking lot with a view of the city, to take in the hazy hot sights of the River Arno and the entire city as the sun went down. I got a spritz and enjoyed the view before walking down. I left the blazer in my apartment before making this journey up the hill alone because boy was it hot and sweaty. I noticed after I got home the sweat had left white stains when it evaporated. -_-

Post-Pitti Bonus Days in Italy

So Pitti was over, and I had some extra days before my flight home. It happened this way because I used Delta miles to purchase the airfare, and you know how you can only get certain itineraries with so many points. Saturday, the day after the last day of the show, I was in Florence.

First thing I caught up with Peter Zottolo at the train station for a coffee—he’d been so busy and we kept trying to meet up, but couldn’t make it happen til the very end. After bidding him arrivederci, I got a ticket into the Santa Maria Novella church. Then I wandered the city a bit. I went to the interactive Da Vinci museum (bring your kids here). I went inside the Duomo. And then Simon Berg, co-owner of Stockholm bespoke tailor Götrich & Co., texted me seeing if I wanted to meet for dinner. We got reservations at Harry’s Bar.

I wore my cream dinner jacket, but put on a dark indigo wash shirt. Frankly I should’ve worn this at one of the parties earlier in the week; not sure why I didn’t think to do so. It was a great and very long dinner with great company.

Walking 100 Miles For Two Days in Rome

I left Florence Sunday morning on a train to Rome. I checked into my hotel, got something to eat, then put on my tan suit and walked to the Borghese Gallery (I did not wear the jacket while walking, but put it on when I was inside the cool museum).

Shop this outfit: Tan linen/silk Spier & Mackay Neapolitan suit | Blue cotton-linen oxford cloth shirt from Proper Cloth | Similar shoes: Alden snuff suede tassel loafer

Afterward I wandered Borghese grounds. It was hot but under the shade of the trees, pleasant even with the jacket on.

That evening I wandered a bit through Rome. My favorite historical site in Rome and probably in all of Italy and actually maybe the world is the Pantheon.

My last day in Italy was a Monday, and many sites are closed on Mondays. But that did not turn out to be the case for the Capitoline Museum, which I’d wanted to see if it were open.

I wore a tourist outfit this day because I was going to do a lot more walking all day in the heat.

Similar shirt: Linen Cavour multi-stripe shirt | Spier & Mackay navy garment dyed cotton shorts | Spier & Mackay navy linen shorts | Sperry tan suede boat shoes

And that was it, off I flew home the next day.

Overall Clothing and Packing Thoughts

It’s a menswear tradeshow, and I’m a tailored clothing guy, so of course I’m going to come turned out. I could have been more efficient, maybe wearing a jacket twice. As it was, I took 5 tailored jackets, including the dinner jacket, one for each day of the show plus the evening, and it was just right.

I had a couple extra shirts I ended up not wearing, but that was fine because I was prepared in case something got ruined or spilled on.

If I return to another summer edition of Pitti, I’ve got a much stronger handle on how to prepare for the heat. But even as it was this time, I think I did pretty well.

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