Opening up my suitcase and sharing my real-life packing list for a winter getaway to San Diego, California.
My deepest apologies to friends and strangers I encountered in the days leading up to our recent trip to San Diego. If it seemed like I was bragging about escaping cold, rainy Charlotte for sunny Southern California, well, that’s because I was.
It’s been a weird winter here in the Carolinas, and though we’ve seen some unexpectedly warm days, we’ve also seen some horrendously yucky ones. Fortunately, I was leaving all of that behind for a weekend of much more pleasant weather—after figuring out what to pack, of course.
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Since this was my first visit to Southern California, I turned to Instagram and TikTok for a little insight into how locals dress for what is arguably their least favorite season (as I mentioned in my travel guide, our friends even went as far as to suggest we skip visiting in winter altogether). From my research, I gathered that the local style falls into two main camps: athleisure (think “just came from a hatha yoga class”) and college-core (so many logoed sweatshirts!).
Neither of those quite fit my style, so I took the casual energy and translated it into my own wardrobe. I packed a mix of classic tops, on-trend denim with a youthful edge, two effortlessly cool coats, easy sneakers, and, of course, a pair of sunnies.
Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter
Everything fit neatly into my carry-on (stay tuned for a review of this unique suitcase soon!), my backpack, or on me, as I wore it on the plane. Here’s everything I packed for three full days and two nights in San Diego—plus a red-eye flight home:
WINTER PACKING LIST FOR SAN DIEGO
WHY I PACKED THESE ITEMS
Tops
Before we left, I told Michael that, in a perfect world, I’d be packing nothing but summery clothes for a trip to San Diego—or at the very least, light and bright pieces. But between the weather forecast and my taco-forward itinerary, I kept my packing list in check with darker clothing.
(I swear I’m not a messy eater, and I actually made it through the entire trip without spilling anything on myself. But I promise you that if I had worn a white tee, it would have been ruined instantly).
Ultimately, I landed on three tops with varying levels of warmth: a black short-sleeve tee*, a black long-sleeve tee, and a soft, neutral cashmere sweater.
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Bottoms
If we hadn’t been flying a red-eye home, I would have just packed my go-to blue jeans and black jeans—but for an overnight flight, hard pants are a no-go. Instead, I brought my wool culottes, which are so soft and comfortable that they’ve become my go-to for long flights over the years.
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Outerwear
A great coat means the rest of your outfit can be slightly more understated, so I packed two: my worn-in leather jacket and an oversized, drapey wool coat. I intentionally chose brown over black to soften my overall look, and I think it paid off.
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Pajamas
I never know whether or not you care about this category, but I include it just in case. For two nights, I packed just one pajama top and one pajama bottom, planning to rewear them. Since I shower at night, I find I can usually get away with a couple of wears between washes—saving valuable suitcase space for more exciting things.
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Shoes
I had a sneaking suspicion that my sneakers would have served me just fine for the entire trip, but I brought a pair of boots as well. They were just the thing to elevate my simple outfit for our nicest dinner and would have gotten even more wear if we’d been in the city for another day. This classic pair is made to order, and the quality really shines.
Accessories
It wasn’t cold enough to justify a hat or scarf, so I gladly left them at home in favor of a belt (the easiest way to tie an outfit together!), some fun sunglasses, and my favorite black crossbody bag of late.
SAN DIEGO WINTER OUTFITS
Saturday Morning
While my flight on Saturday didn’t go quite as planned, I was grateful to have dressed comfortably for what turned into a much longer travel day. Though we missed our flight, I can confidently say my footwear wasn’t to blame—these lightweight shoes feel practically made for airport sprints.
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Saturday Evening
After finally arriving at our hotel—eight hours late—we had about ten minutes to change and get ready for our dinner reservation with friends. Internally, I was flustered, but an all-black outfit and a great coat helped me look far more put together than I felt.
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Sunday
For a packed itinerary exploring La Jolla and Barrio Logan, I kept things casual-cool with light denim and a worn leather jacket to scoot out the door even earlier. We spent part of the day walking along the beach, and my jacket kept the chilly ocean breeze at bay. Even better, I somehow managed to avoid getting sand in my sneakers—always a small victory at the beach!
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Monday Morning
I’m never going to complain about wearing a short-sleeve tee in January. Even with temperatures in the upper 60s, San Diego’s sunshine made it feel even warmer at times. The combination of a short-sleeve tee and a slightly heavier coat was perfect for most of the day, and whenever I got too warm, I simply tossed my coat into the packable tote I always keep in my purse.
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Monday Evening
Before picking up our bags from the hotel, I quickly changed into my planned red-eye flight outfit: a cozy cashmere sweater, soft wool pants with an elastic waist, and a coat that doubled as a blanket. I never sleep well on planes, but I did manage to doze off for a bit, thanks to a simple inflatable neck pillow* and my blackout silk eye mask. And while I was certainly grateful for the chance to sleep in after arriving home, I felt comfortable knowing I was dressed well enough to continue my day if needed.
*This item is no longer available and a similar option is linked
ZIPPING IT UP: MY FINAL THOUGHTS ON MY SAN DIEGO PACKING LIST
One of the perks of flying west? Waking up bright and early, ready to start the day. I took that found time even further for this trip by packing an easygoing, mix-and-match wardrobe with minimal accessories and I don’t regret it one bit.
While I know the summer months are when San Diego truly shines—and a warm-weather packing list would be much more exciting—I actually loved packing for a winter getaway here. The city’s casual atmosphere made it easy to dress comfortably, and I enjoyed wearing some of my cooler-weather pieces without having to bundle up in heavy layers. Best of all, a jacket served as the perfect third piece, instantly making even the most casual outfits feel more polished.
That said, I’d love to return someday to put together a summer version of this packing guide. Who knows? Maybe I’ll even be brave enough to wear a white tee when I do!
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Questions for you
Do you prefer to visit destinations that feel more casual, or more dressed-up?
Do you ever feel spill- or stain-prone while wearing light colors?
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