Everything I Packed For My Trip To Italy

How I planned for a week’s worth of fits I’ll be wearing in Florence and Milan.

Tonight I’m flying to Italy for a week—Florence is up first, then Milan. The main reason for the trip is work: more specifically, I’ll be making videos for Pitti Uomo’s official instagram account all week before heading to Milan for a couple presentations that a few of my favorite brands (namely, Ralph Lauren and Brunello Cucinelli) are putting on. As such, the week-long travel means condensing my overstuffed wardrobe into one checked bag and a tote bag, which is how I arrived at the idea for today’s post: a full breakdown of every clothing item that made the cut.

My approach to packing isn’t about building full outfits in advance. It’s about choosing individual pieces I know can play nicely with pretty much everything else. That means a lot of neutral, solid colors, and it’s a system that ultimately helps me avoid locking myself into any one look, and gives me some room to call an outfit audible if something doesn’t feel quite right once I land.

In theory, that all sounds simple enough, but in practice, I am a chronic over-packer. This stems a little from the aforementioned philosophy that everything should be able to work in multiple get-ups, but mostly from the creeping anxiety that the shirt I wear every week at home will magically start to feel like part of a clown costume once I’m overseas. Has this actually ever happened? Not that I can recall, but the fear persists—and thus the extra garments.

Now, I don’t think there’s actually anything inherently wrong with overpacking (I’ll take it over under-packing any day), but I did try to rein it in this time around. The things I packed are all pieces I legitimately wear often and feel good in, even if I know there’s very little chance I’ll actually wear every single item.

As for the weather: it’s going to be hot as shit—low 90s every day in Florence—so layering opportunities are limited. Still, I’ll be in cities and on camera and technically working, so I skipped anything too overtly “vacation-y.” Translation: I’m heavy on button-up shirts, while I just three pairs of shorts versus five pairs of pants. And oh yeah, zero sandals.

Another small, but noteworthy thing I realized while packing: I think I’ve quietly broken up with the entire “camp collar shirt” genre. Maybe it’s simple fatigue, or perhaps the ones I’ve been trying on haven’t fit quite right, but—while I still see the appeal in theory—every time I’ve tried one on this season, something’s felt off. Maybe I’ll expand on this thought in a future post, but for now my solution was instead of bringing any of those, I packed a bunch of polos—three of which are literally the exact same shirt. (And by the way, are also an all-time classic piece of menswear.)

Anyway, here’s the full packing list—with links—and a quick explanation for why each item got included. Enjoy!!!

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And now, for my packing list…enjoy!