Preppy is both trendy and classic – and admittedly, a little tricky to pull off. If you want to integrate the usual country-club suspects – a classic navy blazer, and penny loafers – into a fresh, modern look, don’t wear them altogether. Instead, pick one, then use it as a starting point. Any of these go-to pieces work well with jeans, a v-neck tee, or a driving cap.

Tommy Hilfiger Navy Cotton Trim-Fit Blazer, $139.99 (from $325), Macys

Sebago Classic Penny Loafer, $115.95, Shoebuy.com
Love,
Loren





