HOW TO WEAR: Kick back in an oversize, broken-in T and loose denim shorts or a Liberty-print prairie skirt.
WHAT TO AVOID: Tucking jeans into boots—that look is better suited to fall.
SHOP THE LOOK: (from top) Suede, 7 for All Mankind, $420; 7forallmankind.com for stores. Suede and canvas with leather trim, Fratelli Rossetti, $740; 212-888-5107. Leather and canvas with brass, Daniblack, $275; 408-354-3355. Linen, Carlos by Carlos Santana, $129; shoes.com.Read MoreLess