Summers in Italy are warm, often hot in major cities, but Italians rarely wear shorts except at the beach, opting for cotton slacks or capri pants instead. Summers in Venice can be muggy and wet, making sandals and open-toed shoes uncomfortable. Pack a stylish, lightweight raincoat and a small travel umbrella no matter the season. In winter, keep warm with a wool coat or jacket, or a tailored vest--fleece and down-filled outdoor wear will label you as a tourist, except in ski areas, of course. More European men are wearing baseball caps, but Italian women favor wide-brimmed straw sunhats for shade from the sun.
Italians make some of the most beautiful shoes in the world for both men and women, but struggling with 4-inch designer heels can be a disaster in the making for tourists unaccustomed to walking on ancient cobbled streets. Athletic shoes usually scream "American tourist," so if you want to blend in and have safe footing, opt for comfortable, stylish leather shoes--loafers for men, low-heeled pumps for women. Don't wear flip-flops, except at the pool or beach; sandals should be worn only in resort areas or with a sundress at a country cafe.
Boots are heavy, so unless you are planning on hiking the hills, leave them at home. Jeans used to be another sign of the "American tourist," but everyone wears them now, during the day, and with a jacket and dress shirt at night at casual restaurants and clubs. Jeans should be sturdy, hide the dirt and hold up for days. But leave the well-worn jeans with holes at home, and remember they do weigh a lot, so take just one or two pairs.
A lot of that Italian art you plan to see is likely inside churches where dress codes are enforced. Shorts, short skirts, bare arms, bare knees, low-cut dresses and shirts are not allowed. Dress modestly and in good taste. While women are no longer required to cover their heads in church, a large scarf is a good idea to take along (or buy an Italian silk one) to cover bare arms or shoulders. Dressing modestly will also cut down on overtures from Italian men. Men should dress appropriately, also, with no shorts or tank tops, and they should remove their hats upon entering the church.
One advantage to trying to blend in by dressing in a casual, but stylish way is that it makes you less of a obvious target for thieves and pickpockets who prey on tourists. Look like a local by leaving the backpack at the hotel and carrying a good leather purse. Travel gear shops sell purses with reinforced straps that cannot be sliced by a knife-wielding, scooter-driving purse-snatcher. Pack a small, folding shopping bag to carry unexpected purchases. Stash your camera in your bag and forget the fanny pack. Men should keep their wallet in an inside jacket pocket or, if wearing jeans, in that hard-to-reach front pocket.
Italians do not wear a lot of jewelry, usually opting for a few simple, but elegant accessories. Makeup is usually simple, and most women do not wear brightly-colored nail polish--again, simplicity and elegance rule. Black is a classic color for both sexes and a great color for travelers. Look for lightweight, stain resistant, crushable dresses, skirts and shirts that can be mixed and matched, plus washed overnight. Accessorize with a scarf or, in the case of male travelers, a classic Italian silk tie.
