How do you fall when it doesn’t quite fall??? This is my first time spending the -ber months outside of New York in a while and I’m already missing the outfits that could be. The extensive vintage coat collection I’ve acquired over the years is unfortunately collecting dust under my bed (which is sad, given I revived them from similar fates only recently). But just because the palms don’t change color doesn’t mean a wardrobe shakeup can’t happen. Where there’s a fashion will, there’s a fashion way.
In New York, my fall has always centered around the question WWBWW? What Would Blair Waldorf Wear? So who was going to fill that void? California is portrayed in a #summerforever lens, with most movies and pop culture centered around beachy sets and styling, so I was having trouble coming up with a grounding reference for this new take on autumnal fashion.
But then it hit me like a Gossip Girl blast straight to a bedazzled sidekick! Who else wears plaid mini skirts, yells at her housekeeper to fetch her designer clothes, and is generally regarded as the queen of everything? Cher Horowitz, of course.
Upon deeper investigation, both online and in my phenomenal gifted coffee table book The Fashion of Clueless, I realized that Clueless is the ~epitome~ of a California fall movie… I mean, it does start on the first day of school. That, like, totally counts!
In this issue of The Dressing Room:
How to get into the spirit of fall without the leaves
Style Icon: Cher Horowitz (What would Cher wear?)
The Yes Pile: All the fits and bits I’ve been loving lately
Seems it never rains in southern California (even when you kind of want it to)
I’ll be honest! One of the reasons that I decided to move back to San Diego was because I got the winter blues. Even after 5 years on the east coast, my California blood could only handle below freezing temps for so many weeks in a row. But I’d be lying if I said I wasn’t missing the fall season in the City.
It’s the cycle of the seasons that’s just so ~romantic~ and dreamy. The perfectly crisp air is so fleeting that you do everything you can to catch it. There’s a sense of urgency to enjoy the moment. The crackling leaves act as warning cries to go outside and see them before they’re gone. It’s very this:
“Life starts all over again when it gets crisp in the fall.” The Great Gatsby
Southern California doesn’t quite autumn in the physical manifestation of the word. Most trees stay green and the temperature’s a steady 70 degrees. So I’ve had to look a little closer for those transitional moments that signal the end of the year:
Fall flavors taste wonderful cold, too. A pumpkin spice iced latte and a fall harvest salad really do scratch the seasonal itch, even when the outside temperature doesn’t match
Swapping my sneakers for loafers, every single time. Makes me feel dressier and more aligned with my east coast mental state. Wish I could wear my beloved tights…
Curating a cozy vibe by listening to my Autumn Rom Com playlist - what songs should I add?
Fall Style Icon: Cher Horowitz
Blair is the classic, old-money, east coast prep-school queen, and Cher is her sunny new-money, public-school counterpart. Both view fashion as the ultimate form of self-expression, wearing it as both armor and a threat. There’s much that could fit in the the middle of their venn diagram, but for the sake of my current area code we’re focusing on what makes Cher the perfect fall (and winter…) muse.
For starters, her fashion fits pretty perfectly in the ‘warm autumn’ color analysis shade range. Despite her bubblepopelectric personality, she only wears pinks and pastels a handful of times and instead is usually in shades of ~crimson~ (iykyk): the Alaia gunpoint dress in the Valley, the mini for her at-home date with Christian, the bow dress when she gives Tai a makeover, the plaid set when she plays matchmaker with her teachers… and it goes on, and on.
She loves plaid, the unofficial pattern of the season. And her commitment to a preppy uniform is what gives her such a strong connection to Blair. Loves a collar, loves a vest, loves stockings. Here’s what I think she’d be wearing in 2026:
SHOP THE CHER COLLECTION HERE <3
The Yes Pile
All the fits and bits I’ve been loving lately!
Odele Clarifying Shampoo and Leave-In Conditioner - I am extremely picky when it comes to hair stuff and I am beyond impressed with both of these products! SO affordable, too. The leave-in does such a great job at taming frizz and keeping my hair super soft. I posted about it here bc I loved it so much, if you want to see a before and after.
Prequel Half and Half Ceramides and Peptides - A delicious skincare addition. I do a lot of morning workout classes and don’t always want to do a full skincare routine when I know I am going to shower after… but I still need a little something something. This is that something something. My skin drinks this stuff up. I wish they made it in a body serum because I’d buy that, too.
Quince European Linen Ruffle Duvet Set - I don’t know the last time I was so obsessed with my bedding. I get excited to snuggle in bed with this duvet set because of its texture and how breathable it is. My Mom is also pro-Quince bedding. Feels luxurious.
Old Navy Long Sleeve Chiffon Top - So freaking CUTE. I’ve been wearing it with a bralette, high waisted jeans, belt and loafers. Feels like it could have been bought from Doen. So many compliments. I’ve also been living in this striped long sleeve (sized up to an L for an oversized look) and how Cher coded is this workout top?
ThriftBooks - I made my first purchase from ThriftBooks recently! My local bookstore didn’t carry the books I was looking for, so I ordered them second-hand from here instead. I know that buying resale doesn’t give $$$ to the author, so I only shop for books that have been out for many moons. My purchase was Stephen King’s On Writing. I’m sure he can live without the $8 sale.
xx, Caylee
Thank you for reading! If you enjoyed this post you may also love How to romanticize your life (according to self-proclaimed experts) and You know you love me! How to channel your inner Uptown Girl
literally just rewatched the movie, it's so perfect and she's such an inspiration, just like this sub !! love it xx
Clueless night at the library was one of my favorite NY moments with you!! As if! 💁🏻♀️