five days in San Francisco: what I packed, what I wore, what I did
it's always harder to zip your suitcase on the way home!
Last summer, I was supposed to visit San Francisco to see two of my oldest friends. At the most inconvenient moment possible, I tested positive for covid, and spent a lot of money to experience a fever and chills in a creepy old hotel room until I could safely fly home. I saw my friends only briefly while they dropped off food and supplies—devastating! I planned a do-over trip this year for the first week of May, and essentially sequestered myself beforehand to ensure I didn’t fall ill again.
This post is part outfit diary, but also a general trip diary. I was in need of a shake-up, and San Francisco provided some welcome variation in scenery, culture, food, and company. I’m always interested in even the minutiae of other people’s travel experiences and recommendations—hopefully reading this unlocks something for you, too.
Having passively absorbed knowledge of San Francisco’s fickle climate (and also having seen photographic evidence of my SF-dwelling friends wearing sweaters in June and July), I packed with layering in mind. Below is what made the cut:
And here are the outfits that came out of it!
Here’s the day-by-day breakdown:
I took an early flight on Saturday and made it to A’s house by 12:30 PM. I knew I was dressed too warmly as soon as I left my apartment, so the scarf lasted all of five minutes before getting stuffed unceremoniously into my backpack on the LIRR. I wore the loafers specifically because they’d be easier to slip off to go through security.1 I wish I’d changed into my sneakers after I landed, though—loafers + cords + sweater vest + button-up made for more of a scholarly vibe than I wanted to give off on vacation.
In addition to the Bass loafers (exact ones here—I got mine on eBay as well), I’m wearing a Piazza Sempione cotton sweater vest via the RealReal (similar here and here), thrifted striped men’s button-up (similar here), Needles corduroy pants via Grailed (same style, similar color here), Dunst leather jacket via Rent the Runway (exact one here), Coach beanie via eBay (similar here), APC scarf via the RealReal (similar here), and a Sandro bag via Rent the Runway (exact one here in black for under $200). An almost entirely secondhand outfit that took me through the entire day—and it was a full day!
Got a preserved lemon and halva scone at Four Barrel, browsed some vintage shops in the Mission, had a drink at Horsies Market, then an early dinner at Good Good Supper Club (did not take any photos, would recommend everything we ordered but especially the cauliflower and the fried sole). After dinner, we saw Magic Farm at the Little Roxie and stopped by an art show in Japantown hosted by A’s boyfriend’s friends.
On Sunday, we’d planned to be outside for a while so I took the opportunity to layer with the other cotton sweater vest I’d packed. The full look was: a linen t-shirt from Uniqlo (here in XS), a Garnet Hill cotton sweater vest via eBay (similar here), Agolde jeans (many of this style here), and Nike Blazers (so many here). Rewore my necklaces, Sandro bag, leather jacket, and beanie—and replaced it with my Who? Weekly baseball cap (yes, I brought two hats with me that day) when it got sunnier.
A was looking for some rugs and furniture for her new space, so we went to the Alameda Point Antiques Faire, which was honestly a bit overwhelming in scale. Aside from some tamales, we left with nothing. I took a little detour to meet up with
at Bakesale Betty and Roses Taproom! (Yes, she is also the best IRL!) I forgot to take any pictures because I was enjoying the conversation and the food so much—highly recommend getting two desserts in the middle of the day. After that, I met back up with my friends at a vintage furniture shop in Oakland. We had a pre-dinner snack at Outerlands (bread and fried green tomatoes); for dinner, my friend K (A’s twin!) made us a green lasagna, and we brought over some desserts from Bi-Rite (including but not limited to chocolate bourbon mousse pie and crème brûlée ice cream).
On Monday, A and I took her dog to the beach and grabbed coffee and a book (Ultramarine by Mariette Navarro) at Black Bird. I got an iced strawberry matcha latte, a drink that was absolutely created as Instagram bait, so on principle I took no photos. I wore a sweatshirt and leather jacket, which was a mistake—way too sweaty! The outfit that took me through the rest of the day was a black Malene Birger tank top (similar here), Apiece Apart linen pants (exact pair here), thrifted denim barn jacket (better version here), and Melissa sandals (exact ones here), added the Mondo Mondo (here in silver) and Roxanne Assoulin necklace (here in different color scheme) and baseball cap. In the afternoon, we met up with one of A’s friends in Golden Gate Park and shared a burrito from Hook Fish. Later, A and I scrolled Craigslist and Facebook Marketplace for furniture, did a Sculpt Society workout, roasted some vegetables for dinner, and watched Hacks in her bed, which is truly all I wanted from this trip—everything else was just a bonus. 😊
By Tuesday, I was running low on clean clothes. The particular silhouette of this shirt (narrow and long) looks better tucked in, but with the loafers, it felt a bit formal for the day. I wanted my matching blue socks to show, though, so I opted for loafers over sneakers. Other than the thrifted Ralph Lauren button-up (exact one here) and the Madewell belt (exact one here in M and here in XS), everything else I wore was a repeat from earlier in the trip. We stopped at a vintage furniture shop before heading to SFMoMA for the Ruth Asawa exhibit. And of course you know I got some merch. Never met a museum gift shop I didn’t like!
After that, I stopped by a wine shop to get a bottle for each of my hosts, changed into one of my new gift shop t-shirts, and packed my bags to spend my last night with K and her husband—we ordered Burmese food and watched the Warriors game (the closest I got to Jimmy Butler on this trip, sadly).
The next day, I let K’s son choose (age 2.5) my outfit—he selected these DL1961 jeans (exact ones here), another museum gift shop t-shirt2, my Madewell belt, and sneakers. To that I added my leather jacket and both hats, just in case. Walked to the Mill with K for some toast, then walked down Haight and popped into a few vintage shops. A met me there later and we each bought one item at Held Over Vintage: a classic blue French chore coat (on my list of things I wanted to find secondhand!) for me, and a red and white striped t-shirt for her. After lunch at Angiday (kumquat slush punch!), we parted ways and I went to the Maritime Museum. I will never pass up a maritime museum—it is my favorite thing to see in a new city.
A picked me up to have dinner at another friend’s house before my redeye back to the east coast. I was wearing the same jeans and sneakers as earlier, but changed into a COS button-up shirt (exact one here) under my Miami Heat sweatshirt (similar here). Her friends made burgers, and A made these, which now rival Levain for my favorite chocolate chip cookies. I said my goodbyes as dinner wrapped up and headed to the airport with a full stomach, a full heart, and an even fuller suitcase3. (In true Eleanor fashion, I left my beanie on the plane, but I was overdue to lose a hat this winter, anyway.)
So this is what I didn’t end up wearing:
I don’t know what I was thinking when I packed that mesh turtleneck. Maybe to wear as a layer underneath a sweater vest? I mostly wore outfits that worked for day and night, and black mesh didn’t seem as appeal in the morning when I was getting dressed. I think if we’d gone out to dinner one more night, I would have worn the white Proenza Schouler top. The Uniqlo linen t-shirt was there mostly as a layering piece—I didn’t have a particular outfit in mind for it, and I wouldn’t have worn it in this color with either of my sweater vests, so it makes sense that I didn’t end up using it. The Needles pants are the only item I’m really surprised I didn’t wear. I do tend to ‘save’ my favorite items for later in a trip, for fear of getting them dirty early on, which defeats the purpose when I end up not wearing them at all.
As for the rest of my suitcase, I think I did pretty well! It was a cohesive capsule (again, except for the mesh turtleneck…) that kept me appropriately warm (and cool), and the vast majority of the items I brought were tried and true in regards to both comfort and style. Hopefully I’ll get to pack for another SF trip soon.
I keep forgetting they don’t make you take off your shoes with PreCheck! I resisted getting PreCheck for years on principle because it is yet another a form of class stratification until my husband was like please can you do this to make it easier for us to travel together. Anyway, turns out Bass loafers set off the metal detector, which all of the TSA agents seemed to remember as soon as it started beeping—“Oh, yeah, you gotta take those off, there’s metal in the soles!”
Is it lame to wear merch from a city while I’m in that city—like, am I doing the equivalent of wearing the band t-shirt to the concert? Or would it only be weird for me to wear it specifically to the museum?
Not only from my gift shop and vintage purchases, but also because A just gave me a pair of Loeffler Randall boots that she doesn’t wear anymore?! The generosity!
love this & the bay! I wear my vintage 1950s sf sweatshirt almost every sf trip, which came from a bay area vintage seller 💕
Carrying both a beanie and a baseball cap for a midday switch is a real SF way of life. Waving hi from around the corner from Horsie’s! Loved this roundup