You guys know me – I love putting together outfit inspo, and honestly, this one might be one of my favorites ever. I’ve been collecting so many looks lately for all my ladies heading to San Diego – the ones who wanna look stylish, confident, and totally put-together, but still keep that little bit of coastal-cool charm in their style.
The truth is that most city outfit guides fail to impress us. And it doesn’t have to be that way! In this list, I’ll show you multiple approaches to create a San Diego outfit look which also showcases breezy, trendy, and effortlessly cool fashion choices.
So yeah… these are my 20+ cool San Diego outfits you’ll rock year-round (because sunshine, beaches, and chill vibes call for outfits that match that energy 🌴✨). I’m obsessed with every single one of them, and I’m pretty sure you’ll find at least a few you’ll fall in love with too.
20+ Cool San Diego Outfits You’ll Love
Burgundy Leather Jacket with Denim Jeans
You’ve gotta try this burgundy leather jacket with denim jeans for a San Diego evening at a beachside bar! It’s so bold and fun for sipping margaritas. Pair with a small tote and ankle boots.
Camel Trench Coat with Mom Jeans San Diego Outfit
Picture yourself in this camel trench coat with mom jeans, exploring a San Diego art gallery! You’ll feel like a stylish local soaking in the vibes. Pair with a crossbody bag and loafers.
Black Leather Jacket with Blue Mom Jeans
This black leather jacket with blue mom jeans is so perfect for a San Diego night out in the Gaslamp Quarter! I’m all about that cool, city energy. Pair with a small clutch and heeled boots.
Beige Plaid Skirt with Teddy Jacket Outfit
This beige plaid skirt with a teddy jacket is so perfect for a cozy San Diego fall day at a farmers market! You’ll look cute and warm picking out fresh fruit. Pair with a crossbody bag and flat boots.
Khaki Cardigan with Blue Shorts San Diego Look
Can you even with this khaki cardigan and blue shorts? They’re perfect for a San Diego day at the zoo, snacking on pretzels! I’d add a fanny pack and slip-on sneakers.
White Tube Top with Black Polka Dot Skirt
This white tube top with a black polka dot skirt is so cute for a San Diego summer rooftop brunch! You’ll feel flirty and fabulous sipping iced coffee. Pair with a woven clutch and strappy sandals.
Cargo Blue Jeans with Brown Leather Jacket
These cargo blue jeans with a brown leather jacket are so perfect for a San Diego night at a live music spot! I love how it’s bold and ready for dancing. Pair with a small clutch and ankle boots.
Trench Coat with Mom Jeans and Black Top
Picture yourself in this trench coat with mom jeans and a black top, strolling through Seaport Village! You’ll feel like a stylish San Diegan by the waterfront. Pair with a crossbody bag and heeled boots.
Grey Wool Coat with Grey Jeans and White Top
This grey wool coat with grey jeans and a white top is so perfect for a cool San Diego day at the Maritime Museum! I’m all about that sleek, coastal energy. Pair with a knit scarf and ankle boots.
Navy Sweater with White Mom Jeans Outfit
You’ve gotta try this navy sweater with white mom jeans for a San Diego bookstore date! It’s so chic and cozy for browsing shelves. Pair with a structured tote and loafers for a bookish, city look.
Grey Mom Jeans with Black Longsleeve Look
These grey mom jeans with a black longsleeve are so perfect for a San Diego day exploring Little Italy’s street art! You’ll feel artsy and relaxed snapping pics. Pair with a small backpack and sneakers.
Brown Leather Jacket with Brown Joggers Outfit
Okay, this brown leather jacket with brown joggers is perfect for a San Diego evening at a craft brewery! I’m loving how it’s edgy yet comfy for a night out. Pair with a small clutch and heeled boots.
Cream Knit Sweater with White Mom Jeans
This cream knit sweater with white mom jeans is so cozy for a San Diego fall day at Torrey Pines! You’ll look cute and warm hiking the trails. Pair with a crossbody bag and ankle boots.
Denim Shorts with White Button-Down Shirt
This white button-down with denim shorts is so perfect for a San Diego beach festival in the summer! I’m all about that fresh, laid-back energy. Pair with a fanny pack and canvas sneakers.
Black Mini Dress San Diego Outfit
Picture yourself in this black mini dress, hitting up a San Diego rooftop bar at sunset! You’ll feel like a total coastal star sipping cocktails. Pair with a bold red lip and strappy heels.
San Diego Outfit with Black Shorts and White Top
Can we talk about these black shorts with a white top? They’re perfect for a summer stroll along La Jolla Cove, feeling so breezy! I’d toss on a straw hat and slip-on sandals.
Baggy Jeans with Grey Graphic Tee
You need these baggy jeans with a grey graphic tee for a casual San Diego coffee shop hangout! It’s so cool and comfy for sipping iced tea in North Park. Add a crossbody bag and sneakers.
Grey Pleated Skirt with Navy Blue Sweater
This grey pleated skirt with a navy sweater is so perfect for a fall day at the San Diego Museum of Art! I love how it’s preppy yet cozy for soaking in culture. Pair with a structured tote and loafers.
Just a little note - some of the links on here may be affiliate links, which means I might earn a small commission if you decide to shop through them (at no extra cost to you!). I only post content which I'm truly enthusiastic about and would suggest to others.
And as you know, I seriously love seeing your takes on the looks and ideas on here - that means the world to me! If you recreate something, please share it here in the comments or feel free to send me a pic. I'm always excited to meet y'all! ✨🤍
Xoxo Clara
