Everyone’s Wearing Trousers With a Twist This Fall
Like many Gilmore Girls-obsessed millennials, my platonic ideal of a fall/winter wardrobe is one part Rory Gilmore’s preppy-cozy essentials, and one part whatever Max Medina—Rory’s private school history teacher and Lorelai’s one-time fiancé—might wear to coffee on a blustery New England afternoon.
That is to say, warm cable-knit sweaters, plaid layers, and whimsical woolen accessories paired with the hearty, meat-eating trousers of a heterosexual male professor. I’m talking boxy, pleated pants in a heavy tweed or wool. I’m talking about pants that look like they went to Oxford and smoke a single cigar each night after supper. Trousers that sneer down their noses (legs?) at anyone who prefers Charli XCX to Chaucer. The real deal.
Glamour’s weird pants wish list
All of this remains true for fall/winter 2025…sort of. Where in previous seasons I craved Mr. Feenie-core, this year I want that, but a little left of center. Maybe it’s the illusion of a second waistband, or a button-fly closure that sits purposely askew, or a pair of pants that intentionally looks like you’re wearing them backwards. Maybe it’s a stupid number of pleats, or a few extra ties that serve no functional purpose, or a pair of pants that are actually a skirt (or a skirt that’s actually a pair of pants).
What I’m saying is, all I want this fall is a freaky little pair of pants. Trousers with a twist.
There’s no specific criteria for what makes a freaky pant a freaky pant, it’s more of a “you know it when you see it” kind of thing. That’s the beauty of the trend! Everyone can participate without drowning in a sea of sameness, à la the Labubu epidemic of 2025. If they make your mom say, “what?” then they count.
The weird pant trend could be thought of as the natural successor to the “quiet luxury” aesthetic, which spurred a trouser boom (once you look for them, you’ll see the Aritzia “Effortless Pants” everywhere) and barrel jeans. But where barrel jeans play with proportions and cuts, these pants are more about doohickeys and thingamabobs, straps, flaps, and pulleys. There are only so many ways to iterate on the classic trouser while still being able to call them “trousers,” but the weirdo pants of the season manage to create something entirely new and visually interesting without straying too far from the Meg Ryan-via-Nora Ephron-films vibes we crave every fall.
