JAKE WOOLF

Everything I Packed For A Two Week Trip To Europe

The shirts, shoes, sunglasses, and more I'm bringing to Milan and Paris.

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Jake Woolf
Jun 14, 2026
∙ Paid

On Tuesday I’ll be leaving New York City and heading to Europe for just under two weeks. My first stop is Milan, where I’ll be attending a fashion show that I’ll be telling you A LOT more about in the next week or two.

After that I’ll be hopping over to Paris, where the plan is to make videos for socials and interview people (one GOAT in particular) for this newsletter. It’s an exciting trip that I can’t wait to get to, but none of it can happen without first making the important decisions of what the hell to wear while I’m away from home for an extended period of time, not to mention running around two major cities. Meanwhile, the forecast predicts it’s going to be hot as hell, which becomes a particular conundrum when you find yourself in locales that are not-quite as religious as the USA about their implementation of air conditioning.

Now, I’ve said it before, but I’ll say it again, that I am pretty shameless over packer. What can I say? Your boy likes options and the ability to call an audible in the hotel room at the last minute. The idea of being locked into a specific shoe—or god forbid, a specific full outfit—while away from home gives me anxiety, so I’d rather have enough choices where I know there’s a handful of pieces which simply won’t get worn. I’d rather than then the opposite problem. Sue me.

Anywho, the result is 35 items that made it into my suitcase, which sounds like a lot but is, to me, pretty reasonable when you break it down into categories: 10 shirts (including button-ups, tees, polos), 5 jackets, 5 pairs of pants, 4 hats, 3 pairs of shorts, 3 pairs of sunglasses, 1 pair of optical glasses, and 6 pairs of shoes. Oh, and lots and lots of underwear (like many people, I pack underwear like I assume I’m going to have an accident every single day of my trip).

My goal with packing is always the same: bring the stuff that, over the last few weeks, I’ve found myself gravitating towards over and over again. I rarely, if ever, bring something that I haven’t yet worn at all because, to put it simply, it’s unproven in my wardrobe. But if I’ve had it for a minute, worn it, liked the way it looks, and know I feel comfortable in it, then it might make the cut. From there it’s about making the tough choices in terms of pure logistics and, most importantly, luggage capacity.

Below, I broke down every single item that made the cut, why it deserved a spot in my suitcase, and linked out to where you can buy the same thing, whether you’re planning on rocking it on an upcoming trip or in your hometown all summer long. Enjoy!!!

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Everything I Packed For A Two Week Trip To Europe

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