A week in Portland with Window of Imagination’s Jen Szeto

We’re completely in love with Jen Szeto’s Instagram, Window of Imagination. Her appropriately named feed gives us little peeks into her inspired life, where the San Francisco native travels to the most swoon-worthy places and takes gorgeous photos along the way. Recently, she went to Portland and, naturally, we asked if we could virtually tag along on the ride. Jen was nice enough to pen us a little travel diary documenting her adventure, on which she stopped in to visit our friends at Stand Up Comedy to outfit her trip.


Jen wears the Electric Feathers Short Infinite Rope Dress and Suzanne Rae Kimono Dress (similar here) from Stand Up Comedy.

TELL US ABOUT YOUR TRIP! WHAT TOOK YOU TO PORTLAND? Portland is an amazing city. I hadn’t spent much time up there before now – it had always been just a few days stopping in and out along a road trip. I had the chance do some work travel there for an entire week, and since the trip fell close to the 4th of July weekend, my husband and I took it upon ourselves to stay through the holiday. The weather was perfect – we arrived just as a mega heat wave was dissipating, so it was pleasant t-shirt weather the whole time. We had access to a car (which was key), and we rented an Airbnb right in the heart of Alberta Arts District, which provided endless amounts of restaurants, bars and ice cream to try. And the coffee! So. Much. Coffee.

WHAT DID YOU DISCOVER ABOUT THE CITY? After being there for a week, I found many similarities between Portland and San Francisco. Like SF, Portland is really health conscious and offers a variety of outdoor activity options, healthy & alternative restaurants, and a slower paced way of living (compared to say, New York or LA). Portland is seeing a surge in tech companies and creative agencies migrating north, so they are also experiencing a population boom like the Bay Area.

Aside from that, there is just a ton of great, diverse food in Portland, which was pleasantly surprising to discover. I ate out every day and gained about 6 pounds, no joke. I was also wowed by all the fantastic boutiques in the city. There are ton in a few concentrated areas that are all very diverse and well curated. When you combine that with no sales tax, the shopping really couldn’t be beat.

window-of-imagination-portland-lbd“Since I travel a lot, I’ve grown accustomed to packing clothing that are comfortable, versatile and durable.”

TOP 5 MUST-SEE/EAT/DO SPOTS YOU’D RECOMMEND? We explored, ate, and drank a lot, and these are the top 5 things that left me yearning for more (many thanks to Britt, Helen, and Diana for the fantastic recommendations):

Nong’s Khao Man Gai. Their famous thai-style chicken and rice is so simple, yet so delicious. There are three locations for the restaurant – two food carts and one brick and mortar. The food carts serve only chicken and rice, but the brick and mortar serves up a wider variety of rice-based dishes. The magic lies in the fat-drenched rice, as it completes the dish with its extra juiciness and succulent flavor.

The soft serve at Cheese & Crack. We stopped by to try their signature soft serve, which has chocolate ganache filling at the bottom of the cone and espresso dust sprinkled on top of the ice cream. It was the perfect summer treat!

Broder Øst. During the July 4th weekend, Colin, myself, and a friend of ours escaped to the coast and explored Hood River. At sundown, we went into town and had dinner here which serves the most delectable Scandinavian comfort food I’ve ever tasted. We ordered a mishmash of things and everything was a hit. We sopped up the juices, licked our plates, and topped everything off with a few rounds of traditional cocktails. I believe there’s another location in Portland, too!

Ira Keller Fountain Park. I absolutely fell in love with this landmark. The fountain is located in the heart of downtown, and is an architectural sight for sore eyes. Heavy waters cascade from towering, mountain-like sculptures that can be observed from layered concrete platforms. On hot days you can wade through the water (though not recommended) or sit atop the plaza and lose yourself in the soothing roar. It was very quiet the day we visited, so we were able to meander without disruption.

Stand Up Comedy. It’s the most avant grade, nondescript boutique in all of Portland, which houses some of the most forward thinking labels to date. The store’s owner/founder, Diana Kim, has spent the last seven years meticulously curating her selection to perfection, carrying timeless items that perfectly compliment my minimal color / maximum volume palette. Her current location is the shop’s second home. It has unique bones and rare stone from its old jewelry store days that Diana has consciously kept intact.

WHAT HIDDEN GEMS DID YOU FIND? Well, for starters, I realized that the second Voodoo Doughnuts location in the NE is waaaaay less crowded than the one in the SW. So if you’re desperate for that sweet dough, head there.

Secondly, the floral shop inside of Alder & Co, Hilary Horvath Flowers, is one of the best places to pick up an arrangement! Hilary was very sweet and super accommodating… and while I shopped around Alder & Co, she quickly whipped up one of the best bouquets that I’ve ever received!

Lastly, if you ever feel like adventuring outside of Portland, there’s this cool little swimming hole about an hour outside of town called Mosier Creek Falls It’s tucked away from the main road but easy to access via a narrow trail. Once you get there, you’re greeted by a cascading waterfall and two picturesque pools where you can swim, mini-cliff dive and sunbathe.

window-of-imagination-portland-layers“I can imagine coming up with at least a week’s worth of outfit combinations with just these two pieces alone.”

HOW DO YOU PLAN YOUR TRAVEL ITINERARIES? Honestly, by the seat of my pants. I’m not much of a personal planner because I think it takes a little fun out of exploring. Many years ago when I was traveling through Japan, I received some great advice by one of my bed and breakfast hosts. He was a retired Frenchman living life slowly and happily with his wife, and when I checked in, he provided some great to-do recommendations during my stay. Just before we wrapped up our meeting, though, he said, “Most importantly, don’t forget to get lost.” And that has always stuck with me. Since then, I’ve tried not to over plan, but instead take a few cues from friends and leave the rest up to the internet on the day-of.

WHAT IS YOUR GO-TO OUTFIT FOR TRAVEL? I’m a forever fan of Jesse Kamm’s sailor pants – I have two, soon to be three, pairs – so I never leave home without them. Since I don’t have TSA pre-check (yet), I always wear a pair of easy slip-on shoes, like the Martiniano glove shoes, and a non-constricting tee. San Francisco has taught me how to layer, so I also never leave home without a coat (which can double as a pillow on long flights or road trips).

While you’re planning your trip, you can shop our favorite Portland boutiques in one handy place. This way >

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