Four Day Packing Plan: San Francisco | On the Daily EXPRESS


Four Day Packing Plan: San Francisco

I just got back from a Spring Break trip to San Francisco and as usual, the hardest part of the trip for me was figuring out what to pack. I am a notorious over-packer, but I had to be more conservative with my outfits this time to make sure the luggage for our family of four could all fit in a compact car for some of our airport transportation.

The Plan:
For this trip, highs were expected to be in the mid-upper 60s and each day was going to be full of typical San Francisco sight seeing with lots of walking and a couple of boat rides out on the Bay.

I picked out four easy, comfortable outfits and took a quick snap of each one so I could refer to it on my phone each day of my trip to remember what I had planned to wear. I literally did this while I was packing so I was short on time, but it made me appreciate people like Carylee who have turned the flatlay into an art form!

In looking through my outfit plans I felt like maybe I could (and should) scale back a little in some areas:
  • Hats: I originally planned to take two hats. Even though I like the fedora better with certain outfits, I decided not to take it since I was worried I would always have to hold onto it with the wind. Plus it was likely to get squashed in my suitcase. My black & white SD hat stays put and matched everything, so I only brought that.
  • Jackets: I originally planned to bring three different jackets. Everyone else in my family was taking one jacket. Overpacking guilt ensued so I decided to cut back to two jackets.
  • Shoes: I had three pairs of shoes for four days. Again, everyone else was taking one pair of shoes, so I took out my white Converse since they would probably get filthy anyway.
What I Wore:
I pulled the overkill items out of the suitcase and I was off and hoping for the best since I didn't try it all on before I left. But here's how I ended up wearing each outfit (you may recognize some of these from Instagramwith links to the items:

Day One AM: Airport 
Jacket: Gap  / Tee: Old Navy / Necklace: Stella & Dot / Black Skinnies: Express
Loafers: Sole Society / Mint Backpack: Target (Interior started ripping after one day of use so I don't recommend this one)

Day One PM: Begin Touristing
Jacket: Gap  / Tee: Old Navy / Necklace: Stella & Dot / Black Skinnies: Express /  Shoes: Nordstom / Nails: Sinful Colors "Easy Going"

Day Two:
Jacket: ExpressTee: Old NavyNecklace: Forever 21 / Jeans: Nordstrom (Similar) / 
Belt: Express / Shoes: Nordstom / Mint Backpack: Target 

Day Three:
Jacket: Express / Tee: Old Navy / Necklace: Stella & Dot
Black Skinnies: ExpressShoes: Nordstom / Hat: Target

Day Four:
Jacket: Express / Tee: Old Navy / Necklace: Forever 21 / 
Sunglasses: Nordstrom ($12!) / Shoes: Sole Society

And here's how it all looked from the front:

Lessons and Changes:
  • Reduce, Reuse: I packed two different pairs of distressed jeans for this trip and really could have kept it to just one pair and re-worn them like I did with my black skinnies.
  • Stay Warm: I planned to alternate wearing my black and grey jacket but the black one was warmer so I ended up wearing it most of the time since the weather was a little cooler than I'm used to. 
  • Stay Really Warm: I have a lightweight cardigan (shown in the collage below) under my black moto in all of these outfits. I threw it in my suitcase at the last minute and I was SO GLAD I had that extra layering option. 
  • Happy Feet: My Converse were decent for the amount of walking we did (probably close to three miles on the first day) but a pair "real" sneakers would have been better.  Flats would have been a big mistake to wear all day, but they were great for the airport.
The fourth outfit above was my least favorite of the group. I flew home that day made some simple changes when I got home, inspired by this outfit that Noelle wore:
Jacket: Express / Tee: Old Navy / Jeans: Nordstrom (Similar) / Sandals: Nordstrom
Necklace & Cuff: c/o Rocksbox  (use code onthedailyexpressxoxo for a free trial month)

And finally here's a front view of the alternate shoes and layers versions:
Day 1 with Converse / Day 3 with Cardigan /Day 4 with Alternate Jacket & Shoes

And last but not least, I always pack my jewelry in this Prezerve 2-in-1 Jewelry Organizer from Amazon. For this trip I kept it to a pretty minimal stash of jewelry so I was able to only use the smaller case. (It fits inside a bigger case if you're packing a lot of jewelry).
My bracelets weren't even visible with the long sleeve jackets I wore so that was one more thing I could add to the "reduce" category!

After just four days of neutral outfits and suitcase life I was ready to get back to my normal closet options at home. I love black and white and grey and never thought I could get tired of them, but I guess I hadn't fully tested that theory before!

Linking up with:
Alison Lindsey / Tara / Jill & Carly / Alice /  Dawn Lucy / ErikaAndrea and Narci / Fashion Friday



  1. Hey you did so good, I love you kept a simple color palette but yea after a while it gets old. I agree about bringing a pair of real sneakers, new balances are cute and very comfy if you are looking for a pair or maybe some free runs by Nike. It's too bad the mint backpack is not good quality, it's so cute.


    1. Yes, if I have another trip with a lot of walking I will definitely look into New Balance or Nike. And not only did the pockets in the backpack fall apart, it was really hard to get the latch shut on the front quickly, which is a hassle when you're getting your wallet, sunglasses, chapstick, snacks etc. in and out of the bag 452 times per day. A zipper would have been so much better!

  2. These are all great tips. I also just got back from a spring break trip and packed way too much. I brought too many going out clothes and we ended up just hanging out by the pool mostly. I need a jewelry roll like that--I just shoved mine in a ziploc and that didn't work so well.

    1. Ah, it's definitely harder to pack when you're not sure which direction your activities will take! And if I didn't NEED to reduce space I doubt I could have pushed myself to do it as much.

  3. well you know I just LOVE packing posts so much it's a bit ridiculous.
    I don't have converse - I have faux converse from Target, I only just got them because I never really thought converse would suit me because hello clown feet, so I thought I would try out some fake ones first. I was going to take them to europe - they are comfy but you think 'real' sneakers would be better?? i'm so worried, i don't mind looking like a tourist but i definitely thought the converse (or fake ones) looked cuter. HELP ME.

    1. You are a way more expert traveler than me! But for my trip, it was only the first day that we walked a LOT. The other days we did walk but probably under a mile because it was drop off by car, walk down to pier, stand in line, ride boat, walk around Alcatraz, stand in line, ride boat, walk to lunch place etc. A few blocks here and there. For the second day and beyond, Converse were just fine and I would rather wear them for style reasons. Like you, I don't entirely mind looking like a tourist...but if it's not too impractical I'd rather be a little more stylish/cute. But if every day had been like the first I would have hated myself for not having better walking shoes. I think you have to analyze exactly how much walking you'll do each day. If it's going to be a looooot, you'll be glad you have real sneakers. And if it bothers you just crop them out of your photos when all is said and done. LOL. On my trip I kept thinking how ridiculous I am sometimes about caring SO much about my outfit being perfect. NO ONE was looking at me the whole trip. Everyone else is too busy doing their own thing and looking at the sites to care if I wore Converse or New Balance. So it's way better for you to be comfortable the entire trip in terms of having the right layers for warmth and the right shoes for foot comfort so you can DO and see what you want rather than to have the shoes that look the cutest.

  4. I always over pack and need to pin this for reference later! All of these layered looks are super cute!

    Doused In Pink

  5. I'm going on a trip to Europe and these outfits look perfect for the style I'm going for! I need to find a faux-leather jacket like looks perfect!

    1. For really affordable options, I have seen several at Target lately! It might be worth checking out if you want something quick, easy and affordable.

  6. Great post! I always completely over pack and I try every time not to but I just don't have the will power to put stuff back like you did lol! I am obsessed with all these looks! I wear my black leather jacket with jeans and converses all the time! It's usually my go-to during the week because its easy with the kids and running errands in.

    Hope you're having a great week so far <3

    xo, Erica
    Casually Styled

    1. It was hard to put stuff back. I like options! And on the last day when I didn't like my airport outfit I couldn't wait to get home and put on the jacket I really wanted to wear! LOL.

  7. I am horrible with overpacking! I always try to think ahead but bring way too much stuff! I'm going to try to be better with that on our two mini vacations this year.

    1. Glad I'm not alone on the overpacking struggles!

  8. I love your review from after on what you could have done different/better! That will be a great post to refer back to because I never seem to learn. Keeping it neutral is such a great way to get great remix-ability with packing, however, I can empathize on getting back to your full closet for sure :-)
    Kellie @

    1. I keep wishing that packing will get easier but it seems like every trip is quite different than the one before. Either the location or the season/weather or the activities. Always back to the drawing board!!

  9. Oh you know I'm such a fan of packing posts! Though the thought of packing itself is such a daunting task so I'm impressed you stopped dropped and selfied along the way!! And your flat lays!! Tear! I am still freezing from my trip to San Fran in October a couple years ago. Layers and comfy shoes are definite must haves! Hope you guys had a great time!

    1. Are you tearing up in horror at my flatlays?!?! LOL. I normally do something like that when I pack anyway but I just set the stuff on my bed for the pictures. This time I put them on cardboard (by the window) per your recommendation but I didn't have time to make it all look super nice, and clearly you can tell I was quite rushed by the last pic!! LOL. But despite the rumpled clothes I still think the cardboard looks better than the bed so thanks for the tip!

  10. Loving the recap! I have learned it the hard way about jackets and jeans as well, so now I just carry one of each depending on where I go. One of the things I cannot do among shoes is converse, they just dont look good on me...SF is notorious for rampant weather change, even a midwesterner like me feels the ocean chills everytime we travel!

  11. Sounds like a great packing plan Gina. You picked many great, versatile basic pieces which as we saw, you can create many chic, different-occasion outfits with. Enjoy beautiful San Fran!

  12. I love the outfits! I used to be a great packer, but then overpacked SO much for my last vacation that I'm trying to be more mindful of what I pack, and what I'll actually wear!

  13. I love seeing these posts and how everyone packs and I love that you stated what you would do differently! You gave me some good ideas for my upcoming trip! Plus, you look super adorable in everything you wore!!


  14. I am definitely an over-packer. And, I typically never wear 2/3 of what I brought along. I am super impressed with your airport escalator photo - I barely make it on those safely with my suitcase.

    Daily Style Finds

  15. Great post for packing and thanks for sharing! I picked up some ideas for my coming trip. All your outfits are cute!

    From Jing at

  16. great style!

  17. Well you did a much better job at packing for SF than I did when I went late last year! I hate over packing, it's probably one of my biggest pet peeves. I'd rather under pack, and then just wear the same things over and over. I love your outfits! The sneakers especially were smart for so much walking! I had sore feet for about a week after our trip because I just wore flats. Looks like you had a wonderful time!

    1. P.S. I love that I inspired your last outfit back home :) I love blogging!

  18. Yike...sorry to hear about the mint backpack. I learn a learn time ago not to go cheap or fancy with traveling items. I still have my travel backpack that I purchased years ago, it more functional then pretty (wasn't even thinking about fashion when I purchased it). I found the best one that really last is the true leather and well made one (and this me traveling all the time).

    By the way, I really like all the looks, I also find that number two is my favorite. I'm always checking out your blog for my weekend looks :D.

    Kreyola Jounerys | Instagram

  19. Thanks for sharing your thought process on why you packed what pieces, it's so helpful! That's a bummer that the mint backpack started ripping so soon :( It's such a pretty color!


  20. Staying warm was certainly the number one thing I learned about SF... not all of cali is warm! LOL

    Eleventh & Sixteenth

  21. Great tips for packing light and all of your outfits are perfect for travelling, super comfy looking and still so cute!! Also, thanks for your sweet comment today Gina, really glad to have met you through blogging & appreciate all of your help:)

  22. Girlfriend, I'm an over-packer too. IT'S THE WORST. I also get packing-related anxiety, where I pre-panic that I've forgotten to pack something WHILE I'm packing. Oh God. So fun.

    Love your relaxed but chic outfits- and San Francisco is such a pretty city! I was born just outside it (in Fremont), so I'm a little familiar. :)

    Le Stylo Rouge

  23. I'm impressed you got an action escalator shot! I am usually an overpacker but ended up underpacking for our cruise! I didn't have enough outfits and was a bit underdressed. I did not plan well at all. And I always end up packing the wrong things for the weather even though you can look up the forecast for days ahead.

  24. I need to get better about packing less for short trips. I want to bring it all! I may need an outfit change :) Each of your outfits is really cute though.

  25. I think you look like a great packer and I hope you had a great trip! When we went to DC a couple years ago I made the mistake of not bringing sneakers. I bought converse and totally should have brought real sneakers. Walking trips really call for happy feet. Lesson learned. I always think I'll get smarter next time...

    Amy Ann
    The Real Arnolds

  26. What a great post. xx

  27. Great idea to take the pictures so you'd remember what you had planned. I also liked that most of the styles were mix & match so that you could put different things together if you wanted!

  28. All great looks and good packing tips too. I'm a notorious overpacker myself. All your outfit are casual, chic, comfy, & adorable! Thanks so much for sharing with Fun Fashion Friday!
    Dawn Lucy

  29. I think you did great with your packing. I am like you and stick with neutral colors when I need pack light. Funny thing about the converse.... I had to work at a concession stand yesterday for 4 hours with lots of walking around in the little area. My feet were barking at the end of my shift. I really hope there's no next time but if there was, I will be wearing shoes with more support.


    Hope to see you for TBT Fashion link up.

  30. I'm the worse when it comes to packing, scaling it back is the hardest thing to do! I probably have such a tough time because I am also a last minute packer lol. Thanks for sharing your process and tips for your travel. One of these days I'll get better! I so need that jewelry organizer for travel in my life!

  31. Packing takes a TON of practice to get right. You want to have options while still being practical and trying not to bring too many things. I think you did great here. Your grey jacket is one of my faves. I was glad to see you packed it, even if you only wore it once. SF is always chilly so I would have probably packed sweaters instead of tees, especially coming from sunny SoCal!


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