ON THE BLOG

Elegant cursive text spelling 'Office' in dark gray or navy color.

Apple Picking in Oak Glen

Where Fall Finally Feels Like Fall in Southern California

Two young girls in plaid dresses picking apples in an orchard with fallen apples on the ground.

There’s something about apple picking that feels like stepping into a Nancy Meyers movie — cozy knits, crisp air, coffee in hand, and two toddlers in plaid who may or may not actually pick any apples. This year, we headed up to Oak Glen, a charming little mountain town in Southern California that feels worlds away from the suburbs below.

Black dog lying on a wooden surface with a colorful striped blanket in the background.

First Stop: Snow Line Orchard

Come for the apple cider donuts, stay for the charm. Snow Line Orchard is a must for anyone visiting Oak Glen — it’s the perfect place to grab a warm donut and coffee before heading out for apple picking.

Alternatively, you can also visit Snow Line after you’re done apple picking. They have a winery, hard ciders, and live music! 

Next Stop: Los Rios Rancho

Apple picking, pumpkins, corn mazes, and a petting zoo — Los Rios Rancho has it all. With BBQ, live music, and plenty of space for toddlers to run around (and moms to sip cider), it’s the quintessential fall day.

ITINERARY

A woman with sunglasses and a watch holding a young girl in a plaid dress, who is picking apples from a small orchard. The woman is smiling while holding the girl and the girl is reaching for an apple on the tree.

Classic Apple-Picking Attire 

Think classic fall neutrals that photograph beautifully and can handle a bit of orchard mud. Quilted jackets, cozy knits, and timeless denim are always safe bets. For little ones, smocked dresses, quilted jackets, corduroy overall dresses paired with knee-high socks and Mary Janes strike that perfect balance between adorable and practical.

What We Wore

This time of year, I find myself yearning to look like I’ve stepped straight out of a Ralph Lauren catalogue — all tweed, tartan, and timeless charm. That’s hard to pull off in Southern California, where the temperatures seem determined to hover around 80 degrees until Christmas. But a trip to Oak Glen is the perfect excuse to ignore the thermostat and pretend I’m visiting Vermont in the fall. Because, let’s face it, dressing for fall in Southern California is really just and act of seasonal optimism. So I did my best to summon the cool, crisp fall weather in a navy quilted jacket, a cream sweater, jeans, and Hunter boots.

As for the girls, they looked like they’d wandered out of a children’s storybook — matching plaid dresses with sweet apple-button details, knee-high socks, and their little navy quilted jackets (which, if I’m being honest, never actually made it out of the car).

WHAT TO WEAR

SHOP THE LOOK

Navy blue quilted jacket with brown piping, button closure, and a collar, displayed on a mannequin.
A white, embroidered, Victorian-style leaf pattern blouse with buttons down the front and tied ribbons on the sides.
Cream-colored sweater with a stitched golden retriever dog graphic and 'RL' initials embroidered below.
Pair of blue denim jeans with a button and belt loops.
A black Hunter brand rain boot with a buckle strap near the top.
A navy blue quilted jacket with a black velvet collar, gold buttons, and a tag inside.
Child's dress in red, green, yellow, and white plaid pattern with a row of red buttons and ruffled sleeves.
A single white sock with a ribbed top and textured knit pattern.
Pair of brown leather shoes with cutout floral design on the toe area and ankle straps with buckles.

Apple picking in Southern California may be less about crisp air and more about strategic sweater choices, but it’s proof that fall is as much a feeling as it is a season. Days like this remind me that timeless style isn’t just about what you wear — it’s about the moments you create.

FINAL THOUGHTS

Text on a black background reading 'XOXO' at the top and 'Ashley' in cursive below.