How to Style The Preppy Trend for Fall 2025 – Charm

Fall has always been my favorite season for rethinking my style, especially when it comes to finding pieces that can easily transition between warm afternoons and crisp evenings. This year, I’m embracing a collegiate, preppy sensibility—clothes that feel casual and fresh yet still have a particular polish. These are the kind of pieces that instantly add newness to my wardrobe while working seamlessly with my tried-and-true favorites.

This fall for me is about dressing in layers that feel effortless, mixing textures, and experimenting with pieces that bridge comfort and style. Collegiate-inspired looks are never too precious; they’re about ease and personality. A well-loved cardigan, sneakers that take you places, clogs that spark conversation—these are the things I’ll be shopping for, and the things I know I’ll live in. Ahead, I’ve rounded up two key ways I’m making the trend work for me this season.

Go Classic With a Striped Knit

(Image credit: Marina Larroude)

I’ve been reaching for my vintage denim on repeat, and I love building fall layers on top of those classics. That’s where a classic button-down or a chunky knit cardigan comes in, and the one I’ve been gravitating toward is from Ralph Lauren.

The caramel base feels timeless, while the stripes in yellow and red give it an unexpected pop of color—just the right amount of brightness to balance autumn’s earthy tones. It’s the kind of sweater I know I’ll wear with everything: tailored black trousers for a sleek day-to-night transition, corduroy for a cozy texture play, or even crisp white jeans to make the colors stand out.

Shoes are always my “thing,” and right now I’m drawn to two ends of the spectrum. For everyday ease and travel—especially those long airport walks—I rely on chic, simple sneakers. They’re the perfect blend of comfort and style, grounding outfits without detracting from the elevated preppy vibe.