Olivia Rodrigo's Dr. Martens Mary Janes Look So Punk Rock With Fall's Plaid Trend
She's been pioneering the pattern's comeback since August.
A tour of Olivia Rodrigo's closet would reveal every fall pattern on your "must try" list. You name a trend, she's got it: polka dots, rugby stripes, and plaid aplenty. On October 22, she tested tartan for the umpteenth time alongside a cool-girl's signature shoe.
Days after attending the 2025 Academy Museum Gala—wearing vintage Armani Privé Spring 2005 Couture—Rodrigo popped up in New York. She looked every West Village girl in a mixture of thrifted and designer finds. Rodrigo paired a graphic tee with a circa-1990s pleated midi skirt, straight out of a school uniform. The red, beige, and black plaid complemented Rodrigo's '90s-inspired color palette. According to @StyleForOliviaR on Instagram, it recently resold for $45. What a deal, Rodrigo.
She upped the midi's academic aura with chunky socks and Mary Janes. They weren't your average single-strap flats, but a Dr. Martens model: the Elphies in the Cherry Cola colorway. (Its tapered toes featured a subtle ombré effect, from black to burgundy.) Classic Dr. Martens treads platformed each sole.
Olivia Rodrigo doubled as a West Village girl in fall's plaid trend.
Rodrigo was primed for fall with plaid, Mary Janes, and even a cashmere sweater. And yet, one unseasonal select made the cut: the woven basket bag she's owned since July. The $430 Amoria Bag debuted in Rixo's May collaboration with Dragon Diffusion. It's handwoven, unlined, and subtly see-through. Their partnership was made for Rodrigo—she equally adores each brand's handbags. The black rendition, which sold out months ago, remains her signature purse two seasons running.
Rodrigo is spearheading plaid's latest pop up, perhaps driven by Calvin Klein, Burberry, or Bally's Fall 2025 shows. In fact, she kickstarted it long before summer's official end. In late August, she styled a turquoise-and-black shift dress, topped with timeless tartan. Not a single brand stepped up to claim the nameless score. Take it from Rodrigo: Thrift stores are a goldmine for plaid pieces.
Shop Street Style Pieces Inspired by Olivia Rodrigo
