If you want to get a good sense of Florence and the menswear scene during Pitti, you’ll find it in the evening. You can always find everyone after 9:00pm once they’ve finished dinner and gone to every event. Everyone ends up at Caffé Gilli. The place is jam packed with 98% menswear. If there's no space, they're all standing outside and if there's no space for that, they've poured out into the street.
The second hot spot evening scene is Harry's bar on the Arno. It's a chic thing to do. Have a drink at the bar, have a Negroni, have a martini. Harry's bar and Gilli are like my go to places for cocktails.
Before the events, go get an aperitivo and a glass of champagne at Procacci, which is on Via de’ Tornabuoni. It's right next to the Antinori Chapel place and a couple stores down from Loro Piana. You get a beautiful little truffle sandwich with a glass of champagne. It's a perfect entrance into your evening.
My favorite restaurant in Florence? Has to be Buca dell’Orafo, it’s a tiny little hole right around the corner from the Rowing Club of Florence. Incredible ambiance, tiny space. It's typically very, very tough to get a reservation there. But incredible food, amazing steak.
If you’re afraid of rare steak, please do not go to Florence and ask for steak. Bistecca alla Fiorentina is a very specific special thing.
If you ask for anything that doesn't look like it's bleeding in front of you and you want it cooked more, they will not serve it to you. They will be very insulted. Save yourself the embarrassment of some Italian guy yelling at you that you want a overcooked steak. Order something else.