Vacation Outfits: What to Wear, Wherever

Southeastern Asia

Vietnam, Laos, Cambodia, Bali: it's HOT. Pack a Panama hat for shade, Keds for exploring and a one-piece pretty enough to double as a top when tucked into a skirt. And a Steven Alan shirt—it actually looks better the more wrinkled it gets.

Straw Fedora, $24, Pins and Needles, urbanoutfitters.com; “New Romantic” Lattice Ikat Shorts, $128, Free People, freepeople.com; Boyfriend Shirt, $168, stevenalan.com; "Champion Summer" Shoe, $40, keds.com; Sheer Tail Hem Skirt, $49.99, mango.com; “Lucy” Smocked Bandeau Swimsuit, $145, Tori Praver, netaporter.com

Alaska

Make like an American Girl doll exploring the wilderness with a pretty leather backpack, embroidered field jacket and streamlined rain booties comfortable enough to wear all day. Swap regular jeans for pale blue, pretty denim that's polished enough for dinners in town.

"Serape" Field Jacket, $129, Denim & Supply, ralphlauren.com; Newsboy Cable-grain Leather Backpack $326, Superduper, luisaviaroma.com; "Troika" Pullover, $63, Eternal Sunshine Creations, revolveclothing.com; Grey Rubber Bootie, $132, loefflerrandall.com; "Paris" Pale-blue Cropped Jeans, $185, MiH Jeans, netaporter.com

Hawaii

Channel Blue Crush in a neon bikini, boyfriend cut denim shorts and stripey, Baja-style coverups. Pack raffia espadrilles instead of sandals—you'll want something covered for the pre-swim hike to the waterfall.

Espadrilles, $45, Soludos x Opening Ceremony, openingceremony.us; Short “Mara” Cover-up, $200, Lemlem, barneys.com; The “Ex-boyfriend” Short, $195, Adirano Goldschmied, agjeans.com; “Sao Paulo” Triangle Bikini Set, $200, Undrest, madewell.com; "Anytime" Sunglasses, $280, Karen Walker, shopbop.com

Major European Cities (London, Paris)

Take a page from Sofia Coppola's book in standout black dresses and clean sandals. With cat eye sunglasses and a detailed trench, it'll make daytime museum hopping a little more glamorous. Then, for dinner, just rotate in a pair of pumps and a pretty bag.

"Jacob" Bag, $265, Reiss, reiss.com; "Clyre" Cotton Trench Coat, $695, Theory.com; "Ilisa" Sandal, $220, pourlavictoire.com; Off-shoulder Pleated Dress, $290, openingceremony.us; "Benedict" Sunglasses, $185, Elizabeth and James, endless.com

Caribbean

Pack a sleek Bond woman bathing suit, a day-to-night coverup/dress hybrid and a bright sheath to show off sunkissed skin. Then add in a punchy bag and bold, colorful jewelry that'll match your frozen cocktails.

Silk Georgette Maxidress, $350, Charlie by Matthew Sink, netaporter.com; Stone Top Triangle Earrings, $25, topshop.com; Canvas Tote, $735, Proenza Schoueler, netaporter.com; "Agathe" Dress, $495, Rag & Bone, saks.com; Speed Clip Wraparound Maillot, $349, Michael Kors Collection, shopbop.com; Plate Necklace, $510, Holst + Lee, shopbop.com