Sterling Point Has the Perfect Summer-to-Fall Wardrobe—Here’s How to Get the Look
3 min readAs someone who grew up on Gossip Girl and The O.C., I never thought I’d find a teen show that competes with my childhood favorites—then I spent the entirety of last weekend binge-watching Sterling Point. Between the realistic sibling dynamics, the love triangle, and the immaculate soundtrack, it finally satisfied my yearning for a well-written teen drama.
I was struck by how relatable and lived-in the wardrobe on Sterling Point feels. Sure, the show’s costume designer, Marissa Schwartz, employed high-end labels like The Row, Maison Margiela, and off-the-runway Chanel. But they’re layered with vintage pieces and teen mall staples like Brandy Melville and Urban Outfitters, giving each look a balance between aspirational and authentic.
Ahead, I’m showing you how to incorporate the show’s standout fashion moments into your summer-to-fall wardrobe (including a few exact pieces worn on set), from masterful layering to rom-com-worthy knitwear.
The Art of Layering
As soon as Annie touches down on the island of Sterling Point, you immediately see that she’s a fish out of water—albeit a very stylish one. Her outfit is equal parts Manhattan rich girl and ordinary teenager, layering a trench coat and preppy button-up over a white camisole and jeans. Of course, it makes sense that she would sling her Coach Brooklyn Bag (a staple of NYC It girls) over her Tumi suitcase.
The Off-the-Runway Gown
It’s hard to deny how fabulous Annie looks in Chanel—particularly, this drop-waist number pulled from the spring/summer 2023 runway. Her exact dress is hard to get a hold of, but fret not—there are plenty of lookalikes out there. The closest alternative I found is this Simkhai piece, but these lace-accented dresses from Dissh and Bl-nk will achieve the same romantic, high-contrast look.
The Statement Swimsuit
It’s always a treat to see Missi Pyle on screen, and she steals the scene in Sterling Point as Rory’s mom, Denise. Her character’s wardrobe leans into bold colors and patterns, matching her outspoken nature. Here, we catch a rare glimpse of her without a glass of Chardonnay in hand, sporting a green floral swimsuit beneath a bright blue cover-up.
The Going-Out Top
In what will go down as one of the year’s best on-screen clubbing montages (can we talk about that Lana Del Rey needle drop?), Annie keeps it simple in a blue tube top and low-rise jeans. She’s clearly not a jewelry girl, but she does accessorize with black satin ballet flats and later a pair of dark sunglasses to shield her hangover.
The Baggy Bermuda Short
A stark contrast to Annie’s city-girl poshness, Ramona, a Sterling Point native, sticks to practical, boyish pieces and oversized silhouettes. Case in point: this combination of a sporty zip-up and Bermuda jorts. I also found an exact match for her leather clogs: the Blundstone 2421 Originals, which are great for three-season wear.
The ’90s Rom-Com Sweater
Of course, Annie saved one of her best outfits for last. In the season finale, she balances a delicate pair of embroidered shorts with a heathered cable-knit sweater and Hunter rain boots. I can’t help but notice how timeless this outfit looks—her sweater feels like it was pulled straight out of a ’90s Meg Ryan film.
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