Everything I Packed For My Trip To Italy, Round 2

The 36 items that made it into my suitcase for my latest trip to Italy. Plus! My #1 packing rule that I just came up with.

Jul 20, 2025

∙ Paid

You might be feeling deja vu after reading this subject line, but don’t worry—while time is indeed a flat circle, this post is entirely new. That said, I am in fact going to Italy just a month after returning from a work trip that took me to Florence and Milan. This latest jaunt, however, is purely for pleasure. To make a long itinerary short, my girlfriend and I will start our week abroad in Milan before ending up in wine country for a wedding. But while the setting is at least partially the same—as is the season I’ll be there—my packing list looks a fair deal different than it did just a few weeks back.

Sure, a few of the things I’m bringing are essential carry overs from last time, and others are necessary attire for the aforementioned wedding. But the benefit of having just been in Italy is that I learned a lot about what things I actually want to wear—and by contrast, don’t want to wear—in the sweltering heat that is an Italian summer. Don’t get me wrong— I still ultimately care a lot (too much, some would say!) about looking good, and finding that balance between comfort and style is always the trickiest part. But I did my best to pack items this time that are even breezier (knowing full well that Italian air conditioning is very much not it), yet will also make me feel cool (this time in the metaphorical sense) while strutting city streets and countryside landscapes. This led to a suitcase that’s packed with shorts, casual shoes, polo shirts, and a lot of lightweight button up shirts. (Perhaps too many but, I don’t know, fuck it.)

What might be the more important thing to report is that, as I was packing, I came up with what I’ve decided to officially adopt as my #1 packing rule for all future travel. This is the first time I’ve put it into practice so who knows if it’ll stick around long term—but I ultimately think it was a pretty useful exercise. And that rule is this: If you don’t remember owning it without digging through your closet or drawers, don’t pack it.

In other words, sit down and write out a packing list, going strictly from memory to conjure up which things to bring on your trip from the items you own (or would like to purchase prior to departure). Set a time limit of 10-15 minutes. If something doesn’t make the cut during that initial brainstorm, it is instantly disqualified from entering your suitcase. From there, you can edit down what is a must-have, versus a maybe, versus a “I don’t need it.” *

This might seem like a silly made up rule at first (which, hey, it is!), but it’s something that I truly think could save us chronic over-packers and/or over-thinkers from bringing along stuff that we won’t actually wear. As such, all 36 items you’ll find below are pieces that I not only legitimately sport on the regular at home, but have made enough of an impact in my wardrobe that I was able to remember their existence without having to do any kind of digging.

Anyway, let’s get to the list, and as always, enjoy!!!

*a quick caveat: I will make an exception for small accessories like sunglasses, ties, socks, and jewelry, which don’t take up much space anyway.

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Everything I Packed For My Latest Trip To Italy

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Everything I Packed For My Trip To Italy, Round 2

The 36 items that made it into my suitcase for my latest trip to Italy. Plus! My #1 packing rule that I just came up with.

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Everything I Packed For My Latest Trip To Italy

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