Packing for a rainy San Diego

Looking forward to upcoming vacations gets me through so many long workdays. However, packing takes so much planning and causes so much stress. It's even worse if I'm only taking a carry-on, which is the goal for all trips that are less than a week. The last time my sister and I got together, it was below zero in snowy Colorado, requiring my heaviest clothing. This time around we were seeking some much needed sunshine and beach time. Unfortunately, the weather did not agree with our plan. The days we arrived and departed were the warmest with 60s and rain in between.

Packing strategy

Knowing the forecast we still weren't willing to give up our beach vacation, so I planned for summery clothing with warmer layers. I carefully choose versatile items that I could pair with several items I was packing. For example, a single long sleeved top could go with every bottom in my suitcase, covering different weather and activities. I also committed to bringing one warm layer and just two pairs of shoes that would pair well with all of my outfits. As a shoe gal, the hardest part was committing to so few shoe options. The rain in the forecast was the most difficult to plan for. I threw my raincoat in at the last minute, taking up a lot of my precious suitcase space, but I'm glad l did.


We arrived early enough to throw off our traveling clothes and head straight to the coast. Bathing suits and coverups were probably too ambitious, but we were warm enough. I went with my striped, lace up shift dress from Express. In case the weather miraculously changed for the better, I planned to wear this as a coverup for every suit I packed.  Knowing that was likely not to happen, it was also a great casual dress option for strolling through La Jolla.

We were pleasantly surprised to meet so many of the local residents--the seals and sea lions! These guys put on quite the show and really entertained us with their dog-like mannerisms. They reminded me of Jax and his elaborate sleeping positions.

Thursday night we found a sushi restaurant with outdoor seating (under heat lamps) overlooking the ocean. I was excited to have an excuse to wear my floral, cold-shoulder dress from Target's Who What Wear collection. My favorite parts of this dress were the flattering cut and the ability to show off my shoulders, which are one of my favorite features.

Friday: Cinco de Mayo

We took a short road trip to see the Old Point Loma Lighthouse and Cabrillo National Monument.  This area was gorgeous with sweeping ocean views and rich history. We did lots of exploring and also some playing!  This was the warmest of the full days we had in San Diego, so I wanted to get at least one shorts wear in--I am on vacation, after all! I paired them with my pink striped shirt from J. Crew because it had longer sleeves, offering a bit more warmth. I love stripes but pink makes them even more fun, especially on vacation.

At night, we were ready to partake in some Cinco de Mayo celebrations! We found a local Mexican restaurant with a party atmosphere and margaritas. I honestly overlooked the fact that our trip was over Cinco de Mayo when I was packing, but I'm really glad I included this festive maxi dress from Express. With its long length and floral print, it was perfect. I love this dress because it hugs in all the right places, and I feel beautiful in it.


We were out and about in La Jolla and also did a bit of pampering.  We started with an amazing brunch followed by mani pedis. I chose these flared crops from the Who What Wear collection at Target because they were the warmest pedi-friendly bottoms that I brought. I went with the blue blouse mostly because I love a bright blue and black pairing.

Later in the day we wanted to get some more beach time in, even if it was chilly and windy. We threw our gym clothes on (the closest we got to working out on vacation) and explored more of the coast. We found a shore to relax on and catch a few blissful minutes of sunshine. Best moment of the trip!

Later that night we craved Italian and found a wonderful place with a piano bar. I went back to the same jeans I had on earlier but swapped my top for an off-the-shoulder gingham blouse from Banana Republic. It was a very low key outfit yet I still felt fancy. We enjoyed a delicious Italian meal with live entertainment.


Our last full day was the worst weather, with constant rain and low 60 temperatures. I was hesitant to wear white in the rain, but it was my only pair of long jeans and they paired well with my coral pom pom sweatshirt from J. Crew (my warmest shirt). We found a movie theater with lounge chairs and seat cocktail service (what?!) for a dry, indoor option.

Afterwards I threw on my raincoat to walk the coast one more time. We had one last hang out with the seals and checked out a cave we heard about. The cave had a man made walkway of about 150 steps into the opening where the ocean waves lapped in. I've been staring at these ocean cliffs for the last couple days, and here I was standing inside one!

The rain got heavier as the day went on. We met an old family friend who gave us a driving tour of downtown San Diego and treated us to some fried chicken. Again, I stuck with my Madewell white jeans, this time pairing them with a black bodysuit from J. Crew and my AllSaints leather jacket. I loved the combo of high waist with the ultra-slimming bodysuit. Don't worry, I wore my raincoat over my leather jacket when we were outside for short periods.

I was sad to leave this lovely place and my sister behind. Of course it was sunny and gorgeous and I boarded my flight back to New York and reality.

How did my packing strategy do?

Even though I wanted to pack all of my shoes, two pairs of sandals were perfect compliment for every outfit I packed. The Birkenstock Arizona sandals are extremely walkable, perfect for all the exploring we did. We walked to dinner each night, so these Steve Madden block heel sandals added a touch of fancy while still being extremely comfortable.  Both come in many colors to best match your vacation wardrobe.  I also had my leather jacket with me for each cold night. It was the perfect option to keep me in style but also warm.

I wish I had packed more accessories, especially jewelry options. I walked out my door without earrings on, which is very out of character for me. A pair of fun earrings or a neckerchief could've elevated several of my vacation looks while not taking up valuable suitcase space.

I'd like to think that given the circumstances, this was one of my best packed vacations!

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