The only way that you would be able to get away with wearing heeled shoes or boots in the Middle East is to go full blown Texan, with heeled men's cowboy boots, jeans, a fancy shirt with a bolo tie, and a 10-gallon hat. Pretending that you are an oilman.
The Arab countries, especially those with strict Islamic Koranic laws A man wearing any form of woman's clothing or shoes could end up in jail or worse.