What followed became an unexpected experiment in summer tailoring and a reminder that there is more than one way to dress well when the temperature rises.

The trip began with a single glorious night at Villa San Michele, the Belmond property perched above Florence. My room opened onto a small garden overlooking the city below, a fitting introduction to the week ahead and the setting for the WM Brown Garden Party later that evening.

For the occasion, I wore a pair of Solbiati cotton-silk trousers cut with a fuller leg and Hollywood waistband, paired with an entirely unstructured pistachio Fox Sport double-breasted jacket. Underneath was a shirt made from Matt Hranek's Martini Stripe by Thomas Mason.

The combination felt a bit old Hollywood and perfectly suited to the evening. More importantly, it reminded me that ease is often more elegant than effort. The garden party was a  chance to reconnect with friends before the madness really started. Folks  around the industry and with people I often only see once a year in Italy.

The next morning arrived a little earlier than I would have preferred after a long travel day and a couple of negronis that had transitioned directly into work mode. Still, there are worse places to wake up than Villa San Michele.

After a few morning meetings, I made my way into Florence and through the gates of the Fortezza da Basso.

Walking into the Fortezza is always a strange experience. It's a bit like being paparazzi for “normal” people—or at least as normal as a gathering of menswear obsessives can be. Everyone is looking, photographing, greeting old friends, and trying to take in as much as possible before the next appointment.

The first familiar face I spotted was our friend Carlos, appropriately dressed in a Tailors' Keep DB coat cut from a William Bliss wool/linen blend. However, I was still avoiding linen.