As to the fitting of a kilt;
A full traditional style will fit so that the top buckle is at your natural waist. There is then two inches of kilt above that. This is called 'rise'. The natural waist on most people is where you bend side to side. This will allow you to cinch the top straps in, till the kilt will stay in place. When worn properly, the apron should have NO wrinkles or puckers in the apron.
Casual model kilts are 'usually' fitted at or slightly above the naval. Most casual kilts have little or no rise above the top buckles. So they are worn like a pair of old style high waisted trousers you see in movies from the 20's and 30's.
Contemporary kilts can be worn almost anywhere it is comfortable. Some people prefer to wear them low, where you would wear jeans. Some prefer to wear them at the naval.
A word of caution though. It is becoming popular to buy inexpensive kilts that are only offered in one or two lengths. This means that to get the hem of the kilt to hit at proper place on the knee you may have to wear the waist at some place where it may not naturally sit without slipping around. This is why you must cinch it in with a belt.
Even if you are "a gentleman of substance" a properly fitted and sized Traditional kilt will cinch into your natural waist. It also creates a very slimming look when worn there.
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