Travel Capsule: 5 days in Portland, Oregon Fall 2019

japanese garden.jpg

Is this even a travel blog post if I’m not plugging packing cube amazon referral links? Sometimes I feel like I’m the only person who writes travel outfit posts who doesn’t mind  packing up without them.

Got back recently (it was recent at the time I started writing this…) from a short trip to Portland, OR! This was my third time visiting, though the previous two visit were in May and both times the highs were around 100F.

I’m not a travel guru by any means, but I love reading these sorts of write-ups for even mundane trips because it’s neat to see how people think about these things! For a list of all the things I consider while packing regardless of trip, see Travel Clothes: How I create a packing list.


Weather / Environment

  • Portland weather in spring and fall is very unpredictable. I don’t pack until the day before, and even then assume that the weather forecast was done by throwing darts at a chart more than 2 days out. (This was my impression, which was enthusiastically supported by several local folks at my lunch table at the conference.)
    • The first time I went to Portland, I had checked the weather about 4 days before and ended up having to buy an emergency skirt, shorts, and summer dress when I arrived because I had only packed jeans when the forecast ended up at 100+ instead of 70.
    • While it may rain frequently, it rarely rains enough that you need like, a full rain kit with galoshes and an umbrella. According to WolframAlpha, in 2018 most of the days it rained, there was 0.5 inches or less of rainfall.
  • The first half of the trip was in a nice air conditioned conference center, and the second half mostly walking around outside.


  • More walking and standing than in my usual day to day
  • Conference dress code: software engineer casual
  • I was going directly to conference from flight on the first day.

Personal preferences

  • I never know if I want to go super extra at these conferences or enjoy being low key. Part of me knows that it’s a fun opportunity to wear whatever (and up the visual variety for any newcomers to the area so it doesn’t feel like you have to wear logo’d tees and old jeans to be a rEaL dEVeLoPeR) but I also know I always feel really tired during conferences so I opted for something more low-key.

An aside: observations and musings on developer conference fashion

So software developers, particularly those closer to the systems level, are not known for being very fashionable. Think graphic tees + cargo shorts + the uncool type of dad sneakers or sandals. I think this is actually pretty great overall to not have being business dress be the standard (You’re not client facing anyway! As long as you’re clean, why not be comfy?), though how harmful it is for a culture to make people feel like they aren’t “real programmers” if they don’t schlub it is a different can of worms which I will not cover here.

I’ve found that in practice, (as you might expect) most people tend to dress somewhere in the local norm is for “casual” and there are of course many different styles exhibited (including whatever is generically trendy, or more feminine styles). But conferences – especially smaller or crunchier ones rather than large enterprise-y ones – tend to attract more outgoing personalities, and it always seems like there’s a larger percentage of attendees whose fashion sense is a concentrated and flamboyant version of whatever the stereotype is, which I actually find is pretty fun. After spending most of my time on r/femalefashionadvice and Instagram, it’s cool to see people just wearing whatever they thought was snazzy without lugging around buckets of anxiety on whether they look childish or untrendy or even really make any sense as an outfit.

There was noticeably more brightly dyed hair (for any gender) than the average sampling of people on the street, and a lot of those were shorter styles (I suspect part of this may just be that it’s easier to maintain that type of dye with shorter cuts). There were more hats than average. People who seemed like they had a developed personal style tended to err more towards punk/badass styles than soft styles. The woman who had full out rainbow dash dyed hair, suspenders, and a sequined bomber, and cargo pants probably takes the cake for the most exuberant look (closely edging out a presenter who wore the ISO graphic tee and jeans but threw a royal blue metallic jacquard blazer over everything).

There were also a lot of tattoos. I’d guess somewhere between 10-20% of people had at least one visible tattoo, but that seemed to be more of a Portland thing than something specific to the conference folks.

Another thing that was interesting was that compared to San Francisco and Berkeley, there were hardly any women wearing wide-leg cropped pants. Plenty of people in SF wear skinny jeans (probably still more skinny fit or jegging fit than other styles overall), but wide-leg pants are common, at least in the downtown sorts of areas. I wonder how much of that has to do with skinny pants being more practical for rain. I’ve always felt that as long as it isn’t extremely cold, cropped wide legs aren’t a bad option because they don’t soak up water from the ground either.

What I Packed

This collage includes the green skirt I purchased in Portland and wore in one outfit before coming back.

portland fall 2019.png

I packed everything into one hard shell rolling carry-on luggage and one pretty average sized laptop backpack.


(including items worn on the first day)

  • 3 tops
  • 2 bottoms
  • 3 shoes including flip flops because I was staying in a hostel-hotel hybrid with shared bathrooms
  • 1 jacket
  • 1 raincoat
  • 1 set of cute pajamas
  • leggings
  • sports bra
  • 5 underwear
  • 2 bras
  • 4 pairs crew socks
  • 2 pairs no-show socks


In addition to the backpack and luggage.

  1. black faux leather crossbody purse. I put some loose items into it and packed it in the carry-on on the way there.
  2. canvas tote bag

Toiletries, Makeup, and Hair


  • shampoo, conditioner, body wash
  • AHA gel, face lotion, face sunscreen
  • aquaphor
  • hair ties, soft headband (for keeping bangs up while washing face)
  • toothbrush, toothpaste, retainer

Makeup / Hair Styling

  1. primer (Smashbox Photo Finish)
  2. concealer (Makeup Forever full cover concealer)
  3. lipstick (Wet n Wild “cinnamon spice”)
  4. cream blush (Glossier Cloud Paint in “dusk”)
  5. eyebrow gel (Glossier Boy Brow in black)
  6. Rahua leave-in treatment (this is a sort of hair paste that I apply on the ends of my hair)

What I Wore

Day 1: Plane + Conference 73/58F ⛅


I woke up at 3:30 AM to catch a morning flight and got to the conference when the first keynote started!

I liked the tougher utilitarian vibe of this outfit with the almost-hoop earrings.

Day 2: Conference 81/62F 🌤️


Wore a lighter version of the first outfit. It was the poorest performing Instagram post I’ve had this season (although you never know why things may take off or not so I don’t put too much stock in it) but I think it’s one of my favorite sneaker outfits, though to be fair I tend to like anything that pairs these sneakers with this t-shirt. I get a lighthearted 1970s nerd aesthetic from it.

Day 3: Japanese Garden 75/59F ☁️


Did a lot of walking outside in pleasant weather. The skirt’s hiked up a bit too high on the right side pose but I was too lazy to do another take. Tbh I think this top is a little too plain to hold its own without the jacket. Doesn’t look bad exactly, but the delta between the visual interest of the skirt is pretty high.

japanese garden.jpg

The garden was SPECTACULAR. The SF and Seattle Japanese Gardens are excellent and worth a visit, but this one was on another level. They also had the most majestic koi.

The little restaurant inside the garden had good tea, but the food was not particularly tasty and was overpriced. The fried rice tasted like something you could get as a Trader Joe’s frozen entree (okay enough, but not something I want to pay table service prices for). The dessert was fine but tiny.

japanese garden cafe.jpg

I also did not realize the scale of Washington Park until I got there. It’s huge! I took the free shuttle up from the train station and was impressed with how clean and organized the service was. I’d love to explore more of it on future trips to Portland.

Day 4: OMSI + Powell’s Books 77/59F ☁️


I was originally planning to wear the striped t-shirt with the daisy skirt and docs (the pattern mixing isn’t super ~on point~ but this particular combo makes me happy), but the Theme WAYWT prompt for that week was “monochrome”, and I realized that with the green skirt I could do a nearly-monochrome green look.

I used to think monochrome or near-monochrome neutrals was the easiest color combo to make good looking outfits. While it does usually make it easy to not make a bad color combo, I find that I have to be more thoughtful about adding more textures/prints/graphics and keeping at least some shapes in the outfit defined to avoid feeling like a pile of fabric. Here there’s high contrast with the corduroy and the twill and t-shirt material, but the heavier velvet headband ties it together.

OMSI bitters workshop.jpg

I participated a bitters-making workshop at OMSI (the Oregon Museum of Science and Industry) which I found through some events aggregator site for Portland. It was a lot of fun and well worth the $40. We didn’t actually make any of the bitter ingredients ourselves, but rather learned about them and various aromatics that they’re usually combined with, sampled a whole bunch, learned how we could make extracts from scratch, and then mixed two bitters combos.

I didn’t know anything about bitters aside from the fact that they were sometimes used in cocktails so I felt I learned a lot. This isn’t a bartending blog, but if you’re interested in learning more, the book they recommended Bitters: A Spirited History covers pretty much everything they said + has recipes (I bought it from Powell’s books afterwards).

They didn’t have a guest lecturer for this. One of the museum staff who does programming for adults and teens also is a hipster bartender on the side. Because Portland.

Day 5: Flying back 🌧


This was the only day it actually rained! I wore the same outfit as day 1, but with the gray raincoat over it (didn’t bother taking a second pic). One of the reasons I like this jacket for traveling is that I can pop the collar up and get a smidge more neck warmth instead of bringing a scarf. Zipping up results in stocky 50:50 top:bottom proportions with cropped wide pants but at least it goes with the solid utilitarian vibe.


I don’t always make it a point to go shopping on trips, but I was going to visit Powell’s City of Books anyway so I thought it would be fun to check out some of the stores in that neighborhood (plus, there’s no sales tax in Portland 💸)

Free People

I didn’t even realize that there was such a thing as a brick and mortar Free People store until I noticed this one in google maps near Powell’s.

portland free people.jpg

It was bohemian style shopping nirvana, although I realized that their sizing is so inconsistent that it cemented that I shouldn’t get anything from them that I couldn’t try on first (so, consignment only).

I got this super ruffley victorian mourning-esque jacket in small. It’s 100% cotton, super comfortable, (no pockets though), and will allow me to live out my steampunk adventurer dreams.

purple jacket

Also got a padded velvet headband (the “mini Molly” headband) which I’d been interested in from the website (back when I was looking at current headband trends for the Styling Headbands posts). This is the smaller of the two padded headbands they have. I actually liked the over the top effect or the larger one, but I found that it squeezed my head more and was unacceptably uncomfortable (though not so much I would say no one with a head in a common size should try it).

Both pictured in an weekend outfit from later in the month:



I thought that the Anthropologie near Union Square in SF was the final form of an Anthro store (it has a petite section! In store!!), but the Portland one outdoes it with sections for bridalwear and a much larger home decor area. As usual, the store displays were really fun (honestly these are like 70% of the reason I ever set foot into any Anthro)

portland anthropologie.jpg

brb getting some fake greenery and a bell jar for my bedroom

I got the striped “Carter” headband (which I’d been contemplating getting from the SF store) and a corduroy mini skirt.

striped knotted headband

The mini skirt more or less fit and I really liked the design of the corduroy pockets adding lines at different angles, but I do want to get this hemmed about 2″ and realized later when pulling the stock photo for my wardrobe tracker that they sell this online in petite sizing 😑

Buffalo Exchange

I visited the Buffalo Exchange near Powell’s Books, but I went on a Saturday afternoon and it was SO crowded and I bailed after giving all the women’s racks a quick once-over. The place also smelled a bit off (a bit like smokers clothes maybe? I couldn’t place it but it wasn’t good) and the whole experience was headache-inducing so I left after maybe 10 minutes. The prices didn’t seem that much of a bargain anyway ($17-$18 for a top for anything not a plain tee, based on checking a handful of tags).


I also made another failed attempt to find a rain jacket after visiting the Patagonia and Athleta shops. (Quality rain gear tends to be $$$ so I was hoping I could save on the sales tax end.) Neither had any that were both knee length and brightly colored and waterproof (not just water resistant). Spoiler: I finally found one in my subsequent trip en route to New Hampshire.


portland 2019 packing.jpg

I had the sneakers, flip flops, toiletries, and small purse in the other side of the luggage.

Things I liked

  • I was happy with all the outfits, aesthetically. Lots of cheery prints! I’d wear this exact capsule again on another trip with similar weather and activities.
  • The green field jacket was great for travel because of the generous pockets and relaxed fit (comfortable for layering). It went particularly well with combat boots. Having a good outerwear+shoe combo helped unify outfits that might have been a bit stylistically weak with only the jacket or the docs.
  • I enjoyed having cute loungewear instead of a random t-shirt like I usually pack.

Things I’d change

  • I didn’t wear my makeup most of the time. To save on liquids space unless I think I’ll leave all the face makeup at home unless it’s a trip for a wedding or something where there will be lots of photos.
  • I still got a bit cold on the plane. Should just bring a lightweight scarf next time regardless of where I’m heading.

I was slightly overpacked and didn’t end up wearing the yellow top or the leggings, but I’m okay with that. I still had a fair amount of extra space in my luggage on the way in. Overall a pleasant and uneventful trip.

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