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what to wear in mid May-early June in Germany and France?

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I'm going to be all over Western and Southern Germany and in the Alsace area in a few weeks and I'm trying to figure out what I should pack. I don't want to stick out like a sore thumb. Are dark, skinny jeans and riding boots or flats ok for this time of year? What about maxi dresses or long skirts with a cardigan and flats? Bear in mind I'm from the south and chilly is anything below 65. When it's warmer are flip flops (cute ones) a no no? What about shorts?
Please tell me what y'all pack this time of year to still be comfortable, look fashionable but not overload your suitcase.
Also-along those same lines, what are must haves while traveling in Europe? This is our first trip.

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