Vacation Outfits: What to Wear, Wherever

10:00 AM, May 24 2012

By Natalie Matthews

Everyone loves vacation, but no one loves packing for it—me included. No matter how many times I show up at a friend's house or in a foreign country with eight swimsuits, two navy blazers and one insanely high pair of glitter platforms, I don't learn.

I still put more thought into my lone airport outfit than I do the dozen or so I throw into my travel bag. I still search my suitcase upon arrival, waiting for my fingers to press some Narnia-like trap door hiding all the logical things I should've packed.

Of course, it never works. But if it did, that pouch would spill over with all the things in the slideshow below. From Alaska to Asia, there's a starter suitcase for each locale sprinkled with things you could actually, realistically wear all trip long.

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.

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.

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.

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.

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.