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Clothing for Bangkok, Chiang Mai, and Singapore in late Oct/early Nov

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Wondering if we can get some advice on what to wear for Bangkok, Chiang Mai, and Singapore for our trip Oct 25-Nov 6. I am a little unclear about the acceptable clothing and weather needs for this time of year because it seems some guidebooks refer to this time period as the rainy season and others say it will be really hot. I guess there are also differences between Chiang Mai and Bangkok, and I am starting to get a little overwhelmed trying to figure out if I need to start buying hot weather clothes now while they are still in season. I will take an umbrella, but do I need a rain coat, or heavier clothes for Chiang Mai?

It also seems that different guidebooks offer different advice on clothing styles. For example, I've read walking shorts are not ok, but others say they are ok. I realize we need to wear different clothes in temples but even that is conflicting. Shoulders covered, ok - do sleeves have to be full, or is 3/4 ok? Are capris or ankle pants ok, or do ankles have to be covered? Are open toed shoes ok or do they have to be closed? How short is too short for a skirt or dress (i.e. is knee length okay)? What about in Singapore? Are shorts or capris acceptable there?

We are in our 40s so we wont wear tight clothes or look like we are going to the beach, but we do want to be comfortable and generally like to dress fashionably and in natural fibers (cotton, linen, silk - are these ok for the humidity?)

Thanks in advance!

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