Tie a flannel around your waist and throw on ripped jeans with edgy heels and your preppy sweatshirt just got schooled. Rag & Bone Distressed Boyfriend Jean, $297, lagarconne.com ...

No preppy wardrobe is complete without a collegiate-inspired crewneck. Even if you’re not a Yale alumni, this vintage sweatshirt makes for a fabulous wardrobe addition. $99.50.

JW Anderson and Uniqlo Just Dropped a Modern Preppy Collection of Our Dreams Oxford shirts, rugby shirts, and denim are all getting a fresh update for 2025. By Sophie Dweck Published: Jan 09, 2025 ...

Almost 26 years after her death, Princess Diana remains a style icon. But, there's one trend proving more popular than the rest - and that's the preppy trend.