Road Trip To San Diego-Functional Outfits & Ultimate Fun
Our recent road trip to San Diego was filled with breathtaking views, memorable experiences, and, of course, some versatile outfit styling. I planned my wardrobe to be practical yet cute, using a few key pieces in multiple ways. Let me take you along on our trip to showcase my everyday outfits as well as our fun.
Quote of the day: “You can’t steal second base and keep one foot on first.” Unknown
When it comes to dressing for a road trip, comfort is key—but who says you can’t add a dash of style?
I know packing for a trip can be stressful for some people, but I think if you have a checklist and practice, it becomes easier and easier.
This article will include not only my daily looks and essentials but also our experience with our hotel, our favorite breakfast place, and a local tour.
In the past, I have shared many of our travels focusing on the outfits if you would like other examples.
- Summer travel capsule wardrobe—from our Idaho road trip
- Best travel outfits—these from our family Austin trip
- Caribbean cruise outfits
First, let’s talk outfits from our road trip to San Diego, and then I’ll add in the hotel and events.
The Perfect Road Trip Skirt Outfit
Let’s start with my go-to outfit for both the car ride to and from San Diego. It was all about comfort without compromising on style. I chose a lightweight, denim, stretchy skirt that allowed me to sit for long periods without feeling constricted.
Knowing that the ride in the car would be warm, I wore a bright-colored t-shirt. The cardigan was added for when we got out of the car and knew we were going to dinner that evening in San Diego.
One reason for this exact cardigan (as seen worn here last year) was that it worked fabulously upside down.
As you can see below, it transforms into a cropped cardigan by hooking it in the back or front. (I almost like it better cropped).
Insider tip: Here is a video on Facebook of how I “crop” a sweater this way. It works best with collarless cardigans, vests, and tops. But make sure to try all that you have because you may be surprised.
When traveling, one secret is to wear your heaviest/biggest footwear, thus I wore these green boots in the car.
On the way back, I wore the exact same outfit only with a different t-shirt and socks (and undies).
Style tip: A comfortable yet versatile skirt is a Travel essential. My rationale is that it’s easier for bathroom breaks as you don’t worry about pants pooling on a germy bathroom floor either when driving or flying. Wearing a skirt while traveling was an “aha” moment on a flight I took in 2020, and I’m always surprised more women don’t do it.
Exploring Coronado Island: Shorts Meet Tights
Day two in San Diego had us hopping over to explore the picturesque Coronado Island. While December in Southern California is relatively mild, there’s still a bit of a chill in the air—especially when you’re near the water. Enter one of my favorite styling tricks: shorts with tights.
Style tip: Combining shorts with tights gives you the flexibility to wear warm-weather pieces even in cooler seasons. It’s a great way to stretch your wardrobe year-round!
You don’t see the full outfit in this photo because you’ll see it soon enough with my mom and stepmom’s options for this day.
Suffice it to say that this lightweight coat was perfect for our travels. I’ve had it for over 10 years and always get compliments on it because it’s the opposite of basic.
For accessories, I had a crossbody purse that was easy to wear for our activities for the day. And my tweedish scarf.
Insider tip: Fleece lined tights are the best thing since sliced bread for keeping you warm in the winter months. If you don’t like the constriction for your feet, there are footless varieties.
Reworking the Shorts for Balboa Park
The next day, we set out for Balboa Park, a place that offers so much to see and do that you could spend an entire week there. From museums to gardens, it was a feast for the senses—and a chance to reimagine those same shorts in a new way.
This time, I wore a pair of grey sweater tights. They aren’t as thick and warm as the fleece lined ones, but considering the weather was delightful, they were perfect.
Instead of sneakers that day, I wore the boots that were part of my travel look. The advantage of the boots is I could wear thick socks or knee-high socks with them if I needed extra warmth.
Style tip: When packing for a trip, think about how smaller items can make a difference. Tights, socks, and accessories don’t take up much space in your suitcase but can make a huge difference in being warm enough.
I included a poncho from 7 years ago (seen here) thinking it would be a great topper instead of always needing my coat. And I was right.
The necklace (found on Etsy) is one of those from ages ago that can be twisted into all kinds of shapes.
Hotel Z-A StayPineapple Hotel
We stayed at a StayPineapple hotel when visiting Seattle in 2018 and loved the quirkiness of it. So when we saw there was one in San Diego in the Gaslamp district, we decided to give it a go on our road trip to San Diego.
While this isn’t a comprehensive review of our stay at Hotel Z, let me give you a couple of pros and cons.
Pros:
-It was in the middle of the Gaslamp district and very easy to walk to many fabulous restaurants.
-The employees were incredibly kind and attentive.
-They provide water for the guests with a refillable bottle that is BPA-free. In fact, we are currently using it as our water bottle for our dog walks.
Cons:
-It is on a noisy street, so ask for an inside room if you have good hearing and like it quiet.
-There is no restaurant in the hotel. We knew this ahead of time and you really don’t need it.
-No parking is provided by the hotel. We had to purchase parking about 4 blocks from the hotel to have easy in and out parking. Luckily the hotel emailed about this a week before our trip so we could reserve parking ahead of time.
Insider tip: If you are staying in the Gaslamp District, check out the Gaslamp Breakfast Company at 551 J St, San Diego, CA 92101
We loved it so much that we went there all 3 mornings of our trip. All of their waffles are gluten-free and the Mashed Potato waffles were a savory treat.
Rob really enjoyed their coffee and both Nancy and I loved their Golden State Latte.
Things to Do on a Road Trip to San Diego
With the internet and Google, there is no lack of information on what to do in San Diego. But I do think there are a couple of key places to hit.
Coronado Island
Take one of the tours of the Coronado Hotel. We took the Legendary tour and while it is pricey, it gives you so much information that you wouldn’t know otherwise.
You get to go into areas that guests wouldn’t be able to access, and you learn about the history and incredible facts about the area.
Balboa Park
You can’t possibly do everything in Balboa Park in one day, but it’s one of the places you need to at least drive through.
Since we were there on Small Business Saturday, I thought it was appropriate to visit the Spanish Village which is chocked full of artist’s studios and whimsical decorations.
Interesting fact: Balboa Park is bigger than Central Park. Not by much, but Californians laud over that detail.
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