Top 3 Destinations and What to Wear While You’re There
San Diego has that golden-hour glow that makes everything feel a little more beautiful—including you. Whether you’re sipping wine in the hills or wandering through Spanish-style courtyards, this city invites you to show up in style. We picked three destinations that are perfect for a weekend escape, and paired each one with outfit ideas that feel effortless, photogenic, and totally you.
🍷Bernardo Winery
Location: Rancho Bernardo, San Diego
This historic winery is tucked into a charming little village with cobblestone paths, tasting rooms, and artisan shops. It’s romantic, relaxed, and ideal for a slow afternoon with friends or a dreamy date.
What to wear: A flowy midi dress in a soft floral or terracotta tone, paired with strappy sandals and a woven crossbody. Add oversized sunglasses and a delicate gold necklace for that sun-drenched, vineyard vibe. We’re loving this dress because it moves beautifully and looks stunning against the backdrop of grape vines and wine barrels.
If the breeze picks up, layer with a cropped jacket or a lightweight knit.
🖼️Balboa Park & California Tower
Location: Balboa Park, San Diego
Balboa Park is a visual feast—Spanish architecture, lush gardens, and cultural gems all in one place. The California Tower offers panoramic views, and the surrounding museums and courtyards are perfect for a stylish stroll.
What to wear: Tailored wide-leg trousers in a neutral shade, a flowy knit top, and a structured mini bag chic enough for museum selfies. Add sleek flats for a little extra comfort.
Finish the look with gold hoops and a soft linen blazer draped over your shoulders. You’ll look like you belong in every gallery.
🌿East Village Brewing Company
Location: 201 Park Blvd Suite 101, San Diego
This neighborhood brewery is all about easy energy: sunny patios, crisp local brews, and a come-as-you-are atmosphere. It’s the kind of place where you can kick back, catch up, and still feel like your outfit deserves a compliment or two.
What to wear: Go for a pair of relaxed-fit jeans with a little vintage wash, paired with a tucked-in cotton tank or a soft tee in a fresh color. Add a crossbody bag in a neutral tone and some low-profile sneakers or slides. We’re loving these jeans—they’re comfy, flattering, and made for casual hangs.
If you’re heading there later in the day, toss on a lightweight jacket or a cozy cardigan. A little gold jewelry and a messy bun finish the look without trying too hard.
Whether you’re planning a weekend getaway or just dreaming of one, San Diego gives you plenty of reasons to dress with intention. These outfits are designed to move with you and make you feel like your most confident self.