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La Valencia Hotel, La Jolla

We’re painfully biased, but most would agree that San Diego is truly a gem of a city - La Jolla after all loosely translates to the Spanish word, “la joya” meaning “the jewel,” with travelers visiting the area at all times of the year - either to beat the extreme heat in neighboring states in the summertime, or for the snowbirds in the winter. As San Diego locals, we’re fortunate to call this perennial hotspot home - the staycations and day trips never get old as there’s so much to see and do with a different vibe just a bike ride or cruise down PCH away. While we may see gray skies in the mornings and the occasional shower this time of year, our key to dressing for any successful outing consists of layers, layers, layers and appropriate accessorizing. 

Style inspiration and moodboard for San Diego winter outfits

Juniper Straw Tote | $79

Rejuvenation meets glamour in our tried and true staycation spot - La Jolla. When most people envision the beautiful coastal landscape lined with tide pools, sea lions and crashing waves it’s usually somewhere in this little slice of heaven that they’re eyeing. From hiking in Torrey Pines, to taking in the sights at one of the local museums, or grabbing fish tacos in the more ‘down to earth’ Bird Rock area, we could easily pack a full stylish agenda - and suitcase when visiting here. The iconic pink hotel - La Valencia - is in the heart of downtown La Jolla with shops and restaurants just steps away. It’s a great spot to spend a day or two…you may even opt to keep your wardrobe très chic in neutrals so you can color coordinate with the backdrop. A structured basket bag for a pre-spring feel, like our Juniper straw tote is the perfect shopping companion and roomy enough for a few toiletries to freshen up throughout the day. 

A visual moodboard including Leah accessories for California winter style

Soleil Straw Fedora | $110

Coronado Island has been world famous since the early 1900’s with celebrities and former presidents escaping for years to one of our favorite Southern California destinations for an authentic resort vacation. Spend the day at the historic Hotel Del having lunch then head to the beach - one of the most beautiful spots along the California coast. You’ll want to be comfortable, yet pulled together, in leather slides or a pair of white tennis shoes, with a knit sweater draped over your shoulders as most of your time will likely be spent outside strolling through this charming town. A short brim straw hat like our Soleil fedora will keep the sun out of your eyes and provide protection while you’re out and about. 

A collage of what to wear in San Diego during the winter

Night of Stars Fedora | $160, Jude Straw Tote | $62

Over the years, Little Italy San Diego has become so much more than your source of pasta cravings, it has evolved over the years to include modern Italian cuisine, seafood restaurants, and nightlife. It’s walkable, the espresso is always flowing and the choices for where to dine are endless. May we suggest some sophisticated, yet functional flats and an oversized blazer with your roomiest pair of denim for a flattering fit that will withstand the day’s events? We love pairing some statement accessories like our Night of Stars Fedora, a wool felt option that feels a bit fancy, but also free spirited with some layered heirloom jewelry. 

SoCal style inspiration featuring Leah accessories and winter outfit ideas

Salty Straw Tote | $116

Whether you’re looking for a more casual day trip or planning on scouting a new beach spot with the best burritos nearby, do not sleep on North County San Diego - the beaches from Del Mar up the coast through Leucadia and beyond are some of the most special stops along the Pacific Coast. Here you can feel cool in Uggs and sherpa lined clogs in the “winter” with a beachy crossbody bag, like our Salty Tote or Sun-Seeker Straw Bag. While Solana Beach has a laid back vibe it doesn’t lack in style. We love spending time in the Cedros Design District where you can find live music at the infamous Belly Up Tavern, a local brewery (and winery), home decor shops, and even a cafe where you can cuddle up to bunnies (if that’s your thing!). If you’re the more adventurous type - or just a sucker for a great Instagrammable spot, plan on hiking through Annie’s Canyon on the other side of PCH.

Are you planning a winter getaway this season? Why wait for Spring Break when you can take advantage of the beautiful Southern California weather year ‘round? Share some of your favorite places to visit below - is there another San Diego spot that tops your list for an amazing staycation? We would love to help you curate some California style accessories for your next staycation! For any questions or help with sizing and product availability, you can DM us on Instagram @Leah_California, or email


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