This year, Brad and I headed down to San Francisco for Labor Day Weekend with our neighbors, Kevin and Renee. Both Brad & Renee’s birthdays were over the weekend so it was the perfect opportunity to get away. Even though the rest of the country was still enjoying Summer weather, the Bay Area was relatively cold. I was constantly checking the weather forecast prior to our trip so I had an idea of what to pack.

I’ve compiled some tips below to make sure your suitcase is packed perfectly for Labor Day Weekend (or around that time) in San Francisco.

First of all, parking in San Francisco is ridiculously expensive. If you can pack light and take the BART to your hotel, I highly recommend it. We stayed at The Palace hotel which was seriously up the steps from the BART station, and on multiple Muni (bus) lines.

If you’re going to be out and about for most of the day, I highly recommend a nice cross-body purse that has plenty of space for items like a waterbottle and a jacket. Brad always flies with a backpack so we used that while walking around town.

Ok, now for the actual clothing items that I packed (because that is what you really care about, right?).

I pretty much live in jeans and leggings, and our weekend in San Francisco was no different. I essentially needed 4 “day” outfits, and a couple ways to dress it up if we decided to head out to a fancier dinner (spoiler alert: we didn’t really do this). Since the 4 of us also love just hanging out with each other, I also packed some lounging clothes to hang out in the hotel room.

As for each outfit for the days, I planned it around layers (and also packed a jacket just in case). For the flight down to San Francisco, I embraced the leggings for the flight, and added a chambray shirt dress. These Blondo Waterproof sneakers were super comfortable and a fun addition to the outfit.

This outfit was perfect for most of the day; however, it was a bit chilly on the waterfront (because of the wind), and especially when we did our harbor cruise.

Our plan for our first full day in San Francisco was to do a bunch of random activities that would only take a few minutes each (such as Painted Ladies, Lombard Street, etc). I knew we would be walking a bunch so I used the same sneakers as Friday. You might recognize this outfit from my post about short blue Hunter rain boots. It is pretty much the same outfit, but with different shoes.

I loved the layered cardigan, it was perfect for our time walking around the city. I got a little warm; however, that probably had more to do with the elevation gain in our walk rather than the outfit. That evening we went to a *slightly* dressier dinner, so I simply swapped out the wedged sneakers for some leather flats and it was perfect!

I might have underestimated the amount of calf work that happens when wedges and hills met because Sunday I was perfectly happy using my sneakers for our day exploring. We were also going to be checking out Alcatraz this day so I wanted a bit more of a athletic shoe for the day. The rest of the outfit features a pair of skinny jeans and a sweatshirt tunic. Again, I swapped out these shoes for some flats for dinner (although, it turned out to be unnecessary because we basically ended up at a dive bar when other plans fell through).

We had a flight home Monday evening, but still had some time to do final explorations of the area. I definitely went with a more casual outfit since it fit our activities for the day, and it would also be my airplane outfit. A fun tee, jeans, and sneakers were the perfect answer for the final day.

Overall, if you’re heading to San Francisco make sure to pack layers, realize that it is probably going to be chillier (and windier) than you expected, and bring outfits that can easily be dressed up or down by swapping out the shoes.

My suitcase consisted of the following outfits: 2 Pairs of Jeans (I could have done 1), 1 pair sneakers, 1 pair dressier flats, 2 t-shirts (because #options), yoga pants/comfy tee for lounging, layered button down with cardigan top, 2 Tunic tops, and a Wine Faux Suede Jacket.

Have you ever been to San Francisco? What sort of outfits did you pack?