All Of The Clothing Stores, Restaurants, Coffee Shops, and Museums I Checked Out In Portland, OR

Weekly Roundup #125

May 24, 2026

Welcome back to the Weekly Roundup, a newsletter sharing the latest updates about the best brands, products, collaborations, releases, events, and everything else happening in menswear that you should know about.

This week I visited Portland, OR, for the first time, and I’ve shared a full recap of my trip below (including photos and details of all of the places I checked out).

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ALL OF THE CLOTHING STORES, RESTAURANTS, COFFEE SHOPS, AND MUSEUMS I CHECKED OUT IN PORTLAND, OR

As someone who classifies themselves as a “city” person, I’ve always gravitated to cities around the world that are well-known and part of large markets—Los Angeles, New York, Chicago, Tokyo, Rome, Barcelona, and more.

And while I wouldn’t classify Portland as a “big” city, it did surprise me with the amount of “big city” things it had to offer.

There were plenty of bars, breweries, dispensaries, and hipster coffee shops (which I expected based on what I’ve heard from others in the past), but it had a LOT more places to shop than I expected, including a decent mix of menswear spots offering stuff I like, including heritage, workwear, classic, ivy, and Japanese Americana styles.

I’ve added a list below that includes all of the places I stopped by—if you want to skip ahead to check that out, you can, and then you can return here to read more of my thoughts about the city itself.

Now, here’s more about my experience roaming around the city.

I stayed in the heart of the downtown district (like I usually do whenever I visit other cities), mostly because I appreciate having quick access to public transportation, a comfortable place to stay in a hotel designed for Millennials (we stayed at the old Ace Hotel, now called The Clyde Hotel), a decent selection of coffee shops close by, and my favorite thing: places to shop for clothes.

My biggest surprise about Portland was how nice everyone was. Possibly, the nicest people I’ve ever met in the US. Everyone acknowledged my family and me everywhere we went. They asked how we were doing or complimented my son, saying how cute he was or how happy he looked. And we were never ignored or disregarded, which felt amazing.

There were plenty of areas downtown that had a “grungy” vibe to them—slightly dirty, a fair amount of homeless individuals, and a lot of drug use on the sidewalks in broad daylight, but for the most part, everyone kept to themselves, which we were grateful for.

I would not say Portland is “kid-friendly” at all. We walked all over the area, and there were hardly any playgrounds in the city; the ones we did find were full of adults hanging out, smoking, and lacking any children actually playing.

It was weird to be one of the few families walking around during the five days we were there. We had no problems getting around on the public transportation or finding high chairs at restaurants, so that was nice.

Overall, I’m glad to have finally visited, and I had a good time with my family while exploring the area. The next time we visit, we’ll stay further outside the city, perhaps somewhere closer to the forest, rent a car, and explore more of the outdoors.