December 9, 2025 How to Make Preppy Feel Modern
Preppy style has circled back in a big way, but this time around, it’s less country-club costume and more effortless, everyday cool. Think of it as polishing the classics while keeping the vibe relaxed and current. If you’re looking to dip into the trend without feeling like you’ve stepped out of a 1990s catalog, here’s how to give prep school staples a fresh, updated spin.
Start with Foundation Pieces
Crisp poplin button-downs, soft cable-knit sweaters, tailored trousers, and pleated skirts. These wardrobe icons are timeless, but the modern take comes from how you pair them. Try styling an oversized oxford shirt with slouchy denim instead of tucked into chinos, or layer a chunky cable knit over a slip dress for a high-low contrast that feels intentional and cool.
Play with the Palette
Color also plays a huge role in making prep feel new again. Traditional palettes lean classic—navy, white, camel—but introducing unexpected hues like butter yellow, pink, or even a muted lavender can instantly refresh an outfit. Patterns like stripes and checks remain core to the aesthetic, but mixing scales or pairing them with minimalist pieces keeps things from feeling too literal.
Update the Accessories
Accessories are where the shift toward modern preppy really takes hold. Swap penny loafers for platform versions, or choose comfortable slides to ground your more tailored looks. Mini shoulder bags, structured top-handles, and simple gold jewelry bridge the gap between polished and playful. And don’t overlook the power of a baseball cap or crew socks—they add a casual twist that balances out the trend’s more refined elements.
Ultimately, modern preppy style is about blending tradition with ease. It’s a nod to classic silhouettes, but with a relaxed attitude that feels right for right now. Whether you’re pulling pieces from your closet or trading in something current at Crossroads, there are endless ways to make prep feel fresh, wearable, and uniquely you.
