Photo: Devon Jarvis/Studio D

The Look: Hawaii
Say aloha to these island-vibe pieces (think palm trees and frangipani) that are both laid-back and high style.

Sunglasses, Foster Grant, $15; cvs.com for stores. Sandals, $40; reef.com. Tote, $148; tommybahama.com. Top, Clube Bossa, $260; neimanmarcus.com. Hat, Indego Africa x Prymal, $225; indegoafrica.org. Swimsuit, $195; onia.com.

Photo: Devon Jarvis/Studio D

The Look: French Riviera
Breezy pieces featuring Gallic stripes, raffia and a fizzy dose of je ne sais quoi.

Hat, Eugenia Kim, $440; intermixonline.com. Clutch, Kayu, $75; kayudesign.com. Top, $118; solidandstriped.com. Swimsuit, top and bottom, $170 each; seilenna.com. Wedges, Nine West, $89; zappos.com. Tote, Kayu, $115; kayudesign.com.

Photo: Devon Jarvis/Studio D

The Look: Maine
These are pieces for the most fashionable clambake ever—think preppy with cheeky details (hello, lobster-and-lemon top!).

Sunglasses, Tommy Hilfiger, $115; tommy.com. Bracelets, $45 to $149 each; silpada.com. Shorts, $185; jmclaughlin.com. Swimsuit, Vanilla Beach, $45; target.com. Sweatshirt, $98; wildfox.com. Paddles, $63 each; artemare.com. Sneakers, $79; talbots.com.

Photo: Devon Jarvis/Studio D

The Look: Cape Town
Bold, colorful graphic prints and textured fabrics—check out the macrame bikini!—channel the South African city's vibrant, relaxed style.

Sandals, Report Signature, $60; reportshoes.com. Shorts, $75; jcrew.com. Hat, $85; reiss.com. Swimsuit, Top, $160, and bottom, $115; kiini.com. Bag, Miss Mochila, $365; shoplatitude.com.

Photo: Marko Metzinger/Studio D

The Look: Rincón
Neon brights and graphic stripes rev up pieces reminiscent of the surf-happy Puerto Rican town. Sporty accessories—a white rubber-strap watch, bendy sunglasses and slip-on sneaks—add just a touch of the trend if you're not ready to hang ten.

Neoprene hair ties, $8; emi-jay.com. Swim dress, $228; pretasurf.com. Sneakers, $72; zeealexis.com. Sunglasses, $68; toms.com. Watch, Adidas, $85; macys.com. Swimsuit, H&M, top and bottom, $18 each; hm.com.
From the June 2015 issue of O, The Oprah Magazine