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The number one piece of vacation wardrobe advice I give is: don’t buy a whole new wardrobe or dress totally differently from the way you normally do. I understand some people want to escape from their normal lives, but you can’t escape you. If you are more of a jeans and a T-shirt type in regular life, most likely you are not going to transform into a person who feels comfortable wearing fetching little printed cotton shift dresses with cardigans in Montreal or Buenos Aires or Shanghai or wherever. Look at what you like to wear most, then choose the most travel-friendly pieces and work from there.
Plus, being on vacation is not the time to find out that your new shirt gapes in front, that people can see your underwear through that gauzy skirt, or those shoes that seemed so comfortable when you tried them on in the store are giving you a hobbling blister.
By all means, avoid the Ugly American syndrome—shorts, fanny packs, and bright white sneakers do nothing to advance the image of Americans abroad—and you should also make sure that what you pack reflects cultural customs and norms (e.g., cover up in conservative cultures, and don’t wear flip-flops to dinner in Milan). On the other hand, clumsy efforts to totally blend in can just look awkward. If you don’t know how to arrange a scarf or a wrap with panache at home, you won’t know how to do it when you get off the plane, either.
Dark colors of course will stand up better to a week or more without access to a washing machine, but you can also make sure that items most likely to get really rank—like tops—can be washed in a sink and air-dried. For myself, I like to stick to neutral colors like navy, black, and gray, leaving the flash for accessories. In fact, for women, at least, accessories are key. You can do a lot with a supply of scarves, earrings, belts, and necklaces. If it’s going to be chilly, bring an eye-catching coat and colorful scarves or gloves, as those are only parts of your outfit most people will see anyway.
So, to summarize: Use what you have. Be comfortable. Bring washable stuff. Everything should work with other stuff. Now get packing.