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The Infamous "What To Wear" Question

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Yes, that's right, yet another person is going to ask what to wear in Italy. Bring on the snark. ;)

DH and I will be in Italy the last two weeks of September -- three days each in Venice, Florence, Sorrento, and Rome (in that order). We're newlyweds (as in, married last weekend), we'll be on our honeymoon, and we're both 28 years old and in good health.

DH has never traveled overseas, and his wardrobe consists primarily of jeans, cargo shorts, name brand t-shirts/polos, and white tennis shoes -- all of which I gather are no-nos if you don't want to stick out like a sore thumb.

I've read a LOT on these boards and on SlowTravel about wearing clothes that scream "tourist!", but here's the thing: We ARE tourists. We'll be wandering around clutching our Canon camera and our Rick Steves guide book, gawking at everything and clumsily asking questions in broken Italian with poor pronunciation. There's nothing we can do about any of this, so it seems foolish to spend a ton of money on, like, linen pants or whatever. I know it may make us a more tempting target for pickpockets, but I'm kind of thinking of just embracing the TOURIST sign stamped on our foreheads and not worrying about trying to blend in with the locals clothing-wise.

I've also read a lot about what kind of weather to expect, and it seems that late September is pretty difficult to predict: it could be rainy, it'll definitely get cooler at night, but it could still be pretty warm during the day, especially in Sorrento and Rome. Low to mid 70s Fahrenheit for all cities overall is what I mostly keep seeing. Has that been your experience?

The last two complications are as follows: 1) We're going to try, if at all possible, to do carry-on only luggage, based on everything I've read about how much easier that makes everything; and 2) we *will* be on our honeymoon, and we'll have these pictures forever, and we're both in our 20s, so I want to try to bring at least one skirt or dress or something nice so I don't have to feel frumpy in my day clothes when we're strolling along the Arno or riding a gondola by moonlight or whatever. I'm stumped about what kind of shoes to bring, though, that would go with a dress/skirt but not be too hard on my feet. (Ideally I'd love to only bring two pairs of shoes.)

So based on all that (sorry for the novel!), what would you recommend? For myself, here's what I'm thinking, to get you started. Remember this is for two weeks, and we'll be doing a combination of churches/museums and also day drips (Pisa, Pompeii, Capri) where more casual clothing would be acceptable.

- 1 pair of jeans (wear on the plane)
- 1-2 pairs of cotton pants (tan and/or navy blue)
- 1 black knee-length skirt and/or 1 nice dress
- 1 lightweight waterproof jacket
- 1 light sweater/cardigan/shawl (wear on plane)
- possibly 1 pair khaki shorts (I'm torn on this)
- 4-5 tops/blouses, mostly short sleeved, that I can mix & match with all of the above
- 1 pair sneakers
- 1 pair other shoes (what? a balance of style and comfort)

As for DH, any advice is appreciated, but he's especially curious about whether he should take the cargo shorts.

Thanks so much! Please try to keep "Oh, THIS question again" sarcasm to a minimum. :D

Erica

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