Thailand is probably one of the safest places in the world to crossdress openly, so if that's your style then you'll probably have a blast. Just make sure you aren't discarding chewing gum on the floor, you might end up with a hefty fine or spending the night behind bars!
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By showing some discretion about what you wear you will win respect from your Thai hosts. Many Thai people will be wearing black or white, but this isn't mandatory. Tourists aren't expected to dress in the same way as Thai people, but showing respect will be appreciated by locals.
If they agree to go with you and you wish to take her out before the bar closes, you have to pay a fee (around 300-500 Baht) known as a “bar fine”. This is to compensate the bar for the time that she is out of the bar, where she would normally be entertaining and attracting more customers.
Avoid Short SkirtsSo, unless you want to dress up in a Thai school uniform, you're better off wearing something a little longer. Above the knee is considered totally fine, but mid-thigh would be too short.
It's easy to top up, gives you an excellent exchange rate, and you can use it to pay for things in Thailand. As you can see, having cash is still a must in Thailand.