Let’s be honest, Sterling Point has given us plenty to obsess over. The Rory-Ellis debate? Still going strong. The soundtrack? Already on repeat. The romance, drama and Muskoka chaos? We’re obviously invested. But somewhere between picking sides and analysing every plot twist, we found ourselves paying attention to something else entirely: Annie Jacobson’s evolving wardrobe.
Played by Ella Rubin, Annie arrives as a very specific kind of Manhattan girl. Ambitious, organised and always one step ahead, she has a pretty good idea of where she wants her life to go, and her clothes reflect that. Crisp button-downs, straight-leg denim, structured layers, designer accessories and polished separates make up her early wardrobe. Everything feels considered, much like Annie herself.
When we first meet her, getting dressed is clearly part of how Annie wants to be seen. She isn’t dressing simply to look good; she wants to look capable, successful and completely put-together. She’s the kind of girl who already knows what she wants to study, where she wants to go, and probably has a colour-coded spreadsheet somewhere to keep track of it all.
Ella Rubin has spoken about this side of Annie, explaining that her character is far more interested in being seen as smart and successful than fashionable. You can see that in how she chooses to dress. Her outfits aren’t necessarily about making a statement; they’re about looking like she has everything under control.
Costume designer Marissa Schwartz keeps that balance going through Annie’s high-low wardrobe. Chanel accessories sit alongside Brandy Melville, Urban Outfitters, Nike and vintage finds, giving her style a polished edge without making her look like a teenager who wandered into a designer showroom. There’s aspiration, but it still feels young and believable.
Then Annie gets to Muskoka, and somewhere along the way, the clothes start changing with her. The shift happens gradually. Structured pieces make room for tanks, relaxed knits, straight-leg jeans, tiny summer separates, vintage T-shirts and easy layers. She borrows Ramona’s clothes, picks up vintage pieces around the cottage and starts mixing them with what she brought from New York.
As the story unfolds, those choices begin to say more about Annie than her perfectly polished Manhattan outfits ever could. She’s still very much her lost, confused self, but there’s a new ease to the way she gets dressed. Her clothes feel less calculated and more instinctive, as though she’s finally giving herself room to figure things out as she goes.
Take her casual looks: a simple tank with lace-trimmed shorts, a pretty top with straight-leg jeans or a vintage tee with her trusty Frye boots. They still have that Annie polish, but there’s less of the “I planned this three days ago” energy. Some pieces feel borrowed, some feel found, and others look like she simply put them on because she liked them.
Of course, Manhattan hasn’t disappeared completely.
And then there’s the white lace Chanel dress she borrows from Rory’s mother that feels completely her own. From Chanel’s Spring/Summer 2023 collection, the dress is polished and unmistakably New York. Against the laid-back backdrop of Muskoka, it feels like a little piece of the life Annie left behind, while also showing that she hasn’t completely let go of it.
Even her signature Chanel bag and Frye boots start to feel different when they’re paired with a vintage yellow tennis skirt and a basic white tee. The designer pieces are still there, but they no longer define the look. They sit alongside the vintage finds and borrowed clothes, making Annie’s wardrobe feel more personal and lived-in.
And that’s what makes her style so fun to follow throughout the show. Annie doesn’t suddenly transform into a small-town, easygoing girl; her wardrobe simply starts to loosen up as she figures herself out outside of her city and her relationship with her father and brother. The girl who once needed everything mapped out begins making room for spontaneity, uncertainty and, perhaps most importantly, dressing for herself.
Rubin has described Annie’s transformation as learning to dress for “the way that she wanted to feel, rather than the person she wanted to be perceived as.” And that shift comes through in every stage of her wardrobe, from carefully styled Manhattan looks to vintage finds, borrowed clothes and slightly undone outfits in Muskoka.
What makes Annie’s style evolution so fun to follow is that she never completely leaves Manhattan behind. The Chanel bag is still there, the Frye boots still make an appearance, but now they’re mixed with vintage finds, borrowed pieces and looks that feel far less rehearsed.
Somewhere between city polish and Muskoka ease, Annie starts dressing less for how she wants to be seen and more for how she wants to feel. Her wardrobe gets looser, more personal and a little more spontaneous. And for a girl who once seemed to have her whole life mapped out, learning to leave a little room for the unexpected might just be her best look yet.
