Before you book your next round trip to Florence, it’s good to keep in mind that a lot of people go. Some have been going for years as buyers; others are simply fans of dressing well and Italy in the winter. Some parties are invite-only, and the smaller dinners tend to be more business-focused than open affairs. Notable exceptions are our friend Matt Hranek’s infamous WM Brown Project party at Sina Villa Medici and J. Meuser’s block party at Marino Alimentari. It’s important to remember that relationships are built over time around a shared interest in style. Most of these folks are just huge menswear nerds and genuinely lovely people to get to know. We’ve all made friends for life at Pitti.
If you’re not in the industry, another way to build relationships is by being a good customer. For many brands, Pitti is also about content creation in a beautiful setting. If you’ve been buying from a particular maker for years and have a strong wardrobe from them, you may be able to tag along in a way that lets your wardrobe be photographed and used as part of their marketing. That kind of alignment can open a few doors.
We all agree that winter in Florence is the pro move. The city is hot in the summer and packed with tourists, which drives up hotel prices and makes reservations harder to get. From a sartorial perspective, winter offers far more opportunities to dress well — full suits, overcoats, knitwear, and hats. Coming from California, where the seasons don’t shift much, a brisk Italian winter actually feels exciting.
What to do when you get there
For us, it’s packed with meetings and events. Nonstop networking, and a ton of exhausting fun.
A typical day for Tim this January:
8 am — Meet Spencer for breakfast and coffee to go over logistics: what shots we want and what meetings are on the schedule.
9 am — Print Edition release event, breakfast and coffee at Alimentari Marino.
10 am — Fox Bros meeting. Shoot Patrick in his Tailors’ Keep jacket. Also connect with Corgi, Bowhill, and other British makers.
11 am — Walk to the show with Spencer. Meetings and introductions at the show.
Skipped lunch.
1:30 pm — Meeting with Awling (not at the show, about a 30-minute walk).
3 pm — La Bowtique meeting, destination TBD.
4–6 pm — Upload photos with Spencer and call Ryan back in CA about what to post and download about meetings, usually over cocktails. Change for dinner.
6–9 pm — Plaza Uomo party.
9:30 pm — La Bowtique dinner, black tie.
After — Drinks at Fiddler’s Elbow.
That day, Tim walked about 28,000 steps.
All of this to say: Florence is always a good idea, whether or not you’re there for Pitti. Here’s our guide to places we trust and have grown to love.
DRINKING
Art Bar- It’s a small spot with an easy, cool energy and stiff cocktails. The room has that slightly bohemian feel without trying too hard, and you get the sense pretty quickly that you are hanging with the regulars. The line between patron and staff is a bit blurred, in a way that makes the whole place feel relaxed and familiar.
Fiddler’s Elbow — Of course an Irish pub in the middle of Florence becomes the gathering spot during Pitti. Jackets come off, ties loosen, and the conversations get better than anything that happened on the floor. Guinness in hand, people spill into the square outside — the kind of place where 2am sneaks up before you know it.
Harry’s Bar Firenze - is one of those places that doesn’t require a menu — dark wood, leather, career bartenders, and you stick to the classics. During Pitti it’s always drawn the well-dressed crowd, and the legend level went up when Matt Hranek launched WM Brown Project magazine at the original location, a proper night that ended with a €14,000 bar bill that’s now part of menswear folklore. Now reopened at Sina Villa Medici, it still carries that polished, slightly indulgent energy — and these days Matt throws his party by the pool at the Medici, just a few steps from the bar.
Caffè Gilli — A reliable stop on Piazza della Repubblica. Polished wood, glass pastry cases, and true old-world atmosphere. Great for espresso, an afternoon Negroni, or meetings.
EATING
Trattoria Sostanza — Old-school, no-nonsense, and proudly stuck in time. You go for the butter chicken. Tight room, shared tables, and the kind of place where the walls feel like they could tell you amazing stories.
Trattoria Camillo — Feels like someone’s very stylish Florentine aunt is running the dining room. Good when you want classic Tuscan without feeling like you’re in a reenactment. Although our buddy Chase suggested the curry chicken… and it was a great move with a carafe of red.
Arnie’s — A proper sandwich stop when you don’t want to overthink it. Order and eat back out into the street. Perfect between shops and meetings or when you realize you haven’t eaten and suddenly need to fix that immediately.
Mariano Alimentari — This year between the Central Division breakfast events and the J. Meuser street party we spent a lot of time here. It is a part of the Pitti fabric now and deservedly so.
CULTURE
*we never get to do as much as we want due to a lack of free time
David — Seeing Michelangelo’s David in person is a different experience than any photo can prepare you for. The scale, the tension in the hands, the expression — it feels less like a sculpture and more like a presence in the room. The original stands inside the Accademia Gallery, while a replica holds the statue’s former spot outdoors in Piazza della Signoria, where the real David stood for centuries. It’s a reminder of the level of artistry Florence gave the world and why the city still feels like the center of a long creative lineage. And it doesn’t stop at museums — sculpture is everywhere in Florence. Piazzas, fountains, building facades, and street corners are filled with figures carved in stone and bronze, so even a simple walk across town turns into an open-air gallery. Walking the city, you start to understand the kind of obsession and physical devotion described in The Agony and the Ecstasy — that sense that art here was wrestled out of stone, not simply designed.
Santa Maria Novella — It dominates your eyes as you seem to pass it a million times. Then when you step inside you’re standing in front of centuries of art. Marble geometry outside, fresco overload inside, and a sense of awe the minute the door closes behind you.
Uffizi Gallery — You’re basically walking through the greatest hits of the Renaissance, room after room of paintings you’ve seen in books your whole life. Spend the whole day there, do the audio tour.
Boboli Gardens (the Medici gardens) — When the city starts to feel like stone and museums, this is a good reset. Big views, long paths, and statues. It is a perfect and beautiful way to walk off the days of pasta and drink.
Florence overall — The city is Renaissance art casually existing next to your morning coffee. History and craftsmanship are part of daily life, and it’s a place we always love coming back to. Walking along the Arno River at dusk, when the light hits the buildings and everything slows down for a minute, is one of those simple, perfect Florence moments.
It’s also the place that gave rise to what’s now called Stendhal syndrome, named after the French writer Stendhal, who described feeling physically overwhelmed by the art here. After visiting Santa Croce Basilica, he wrote, "I was in a sort of ecstasy, from the idea of being in Florence, close to the great men whose tombs I had seen. Absorbed in the contemplation of sublime beauty, I saw it close up, I touched it, so to speak."
That’s Florence — beauty not as something distant, but something you walk through and see everywhere. Add beautiful clothes and amazing friends, new and old, and it becomes a recipe we want to repeat.

