Early autumn in Italy is prime time to visit as temperatures are pleasant and tourist crowds have thinned out. With fewer foreigners around, however, it's easy to stick out like a sore thumb. To avoid the packing pitfalls of fellow tourists, approach clothing with the same attitude that Italians have about cooking: Start with simple classics and add a little flair.
Though Italy's climate is generally mild and comfortable, its reputation for balmy Mediterranean temperatures year-round is slightly exaggerated. Weather is still warm in late September, but rainfall can be common, so pack rain-resistant boots and a light weatherproof jacket. This is especially important if you'll be touring Venice. Although the city's canals typically rise and flood in winter, this has been known to occur in autumn as well. In October, temperatures are not extreme, but the averages tend to drop from September. Skip the heavy-duty winter coat, but pack a sturdy jacket and a few sweaters that can keep you warm and cozy on brisk days.
Whether visiting the monumental churches of Rome and Vatican City or wandering farther off the beaten track in Ravenna and Genova, Italy's sacred spaces require visitors to wear modest clothing. Keep shoulders, legs and chest areas covered and avoid wearing anything with potentially offensive slogans or images. Failing to dress conservatively may mean being booted out of historic religious sites – or even being forced to don a lampshade-like garment to cover up. Another sartorial choice to avoid is loud prints or flashy neon colors. You won't get kicked out of churches and museums, but you'll stick out like a sore thumb in the sea of Italians in their classic fall neutrals.
No one will expect you to dress like a Milanese model, but Italy has earned its fashionable reputation for good reason. Avoid sweatpants, athletic shorts and T-shirts. To blend in with the locals, take note: Italians tend to dress for the season, not the weather -- so, even if temperatures are warm and the sun is out in October, the majority will still pile on several layers. Tailored trench coats are a perfect fall outerwear choice for both men and women. For shoes, comfort is key -- you'll be doing a lot of walking, mostly on cobblestones -- but you don't have to sacrifice style. Rather than tennis shoes, opt for suede or leather boots or oxfords, preferably in black or chocolate brown.
Accessories and Additional Notes
Weather in September and October in Italy can vary dramatically depending on the region, especially given that the country stretches from the Austrian and Swiss Alps down to sunny Sicily, Calabria and Puglia, where the warm winds blow in from the Sahara Desert. Everything you pack should be conducive to layering -- prepare for the unpredictable. Use accessories for added warmth and style. Women can take light shawls or scarves, which can be useful on crisp October evenings. This is particularly true if you'll be in Florence, which is encircled by hills, resulting in occasionally harsh temperatures. Men also shouldn't shy away from scarves, as many Italians wear them and they can both keep you warm and brighten up an outfit. A travel bag is also a must, and no one will look twice at a man with a leather satchel.