What Not to Do in a New CityThe cafes of Paris, the shops of New York, the restaurants of Tokyo: there's nothing like an urban vacation to bring out the sophisticate in all of us. Whether you plan to hit up every museum in Florenceor hop the food stalls in Singapore, you'll want to make sure that you have clothes with you that mark you as a savvy insider, not a country bumpkin.
Overall Plan: Think chic and simple. Look for items that pull double duty, with colors that complement each other; in most cities (the Southern U.S. excepted), it's hard to go wrong with basic black. Try not to overstuff your bag, as there's nothing worse than trying to wrestle a monster suitcase onto a bus or through a subway turnstile.
What's Essential? Invest in a pair of good walking shoes that could also be worn to a nice restaurant (Merrell and Clarks have great ones that have an urban vibe). Try them out before you go, as you don't want to be limping through a city with blisters. For women, you can't beat a pair of skinny jeans and stretchy black pants that can be worn while walking around during the day, and then out again at night paired with a dressier blouse or top. Instead of a backpack, look for a purse or bag that has a thick shoulder strap that can't easily be cut, and can be worn messenger-style against the body to ward off thieves. For men, a lightweight travel blazer or sport coat can be all that you need to go from a museum to an evening out (wear it on the plane to save suitcase space).
Secret Weapon: A couple of colorful scarves don't take up too much room, and can transform a blah outfit -- or hide the fact that you've worn it already.
Safety First: A rubber doorstopper can be a girl's best friend in an unfamiliar city. Stick it under the hotel door if there's no security lock, or under the door of an adjoining room. (See also A New Way to Stay Safe in Your Hotel Room.)
Leave at Home: Even when it's hot out, women might consider skirts or loose-fitting, lightweight capris instead of shorts, especially if you'll be visiting churches or other religious structures. And while men might not go anywhere back home without wearing their showiest watch, it's all too easy to take a wrong turn in an unfamiliar city. A good rule of thumb: If you don't want to lose it, don't bring it.