It's always hard to dress for a trip to another city. No one likes to stand out immediately like a tourist with a fanny pack and sneakers, unless you are hoping to get ripped off or receive bad service. I have always loved a shirtdress, hence the start of JDCamicetta, based initially on Jane's and my annoyance at the lack of good shirtdresses in the shops. Since a shirtdress is never trendy it suits any city and it is polished enough to take you into posh shops and restaurants. It's also the easiest thing to pack - no worries about what to wear with it. Flat sandals and a belt for day, a heel and a pretty purse for evening.
Read here about The Telegraph's fashion writer Lisa Armstrong's day in a shirtdress http://fashion.telegraph.co.uk/news-features/TMG8943897/What-Im-Wearing-a-shirtdress.html.