It might sound silly, but in fact, I think it’s a good idea to think about the clothing that you will take with you when you travel.
Personally, I give it a lot of thought, especially since I usually travel with just one shoulder bag to carry everything. This is whether I am going to Morocco, Turkey, Europe, Asia, or North America.
The first rule is bring things that will work together in a variety of ways. You may love that one outfit but if it doesn’t go with anything else, you are wasting space. Make sure all of your pants can go with all of your shirts.
Here is my list of travel clothing:
1) 1 pair lightweight cotton pants. Mine have loose bottoms so they can be rolled up easily and worn as shorts.
2) 1 pair convertible pants/shorts with zip off legs
3) 1 nice button down shirt
4) 2 t-shirts
5) 3 pairs of underwear
6) 3 pairs of light socks
7) slippers (thongs, flip flops)
8) comfortable loafers
9) A light sweater or jacket
10) A hat
11) my sarong, which is the most versatile thing I own. I use it for a towel, a blanket, a bag, a changing room, and about 100 other things)
12) board shorts
And as to travel underwear. I never have had them, but I’ve had so many people I respect tell me that ex-officio underwear are the best that I can recommend these. A lot of travellers prefer canvas clothing like carharts, but I like wool because it keeps you warm even when it is wet. You can find cheaper items, or just bargain hunt at thrift stores and garage sales.
When you fly or take the bus, wear your ‘heaviest’ things. For me that’s the loafers, button down shirt, and trousers. That way you have a lighter bag for carry on regulations.