I think Bryan may be wanting to buy his belt at the same time as his kilt, so he can't put his kilt on first. The top of most kilts are worn higher than pants. Close to the belly button area or higher.

This is where you should measure.

When you see kilts worn with the belly flopping over the front, it's because the wearer has allowed the flop-over to happen, and should take the time to pull his kilt up, and tuck his belly in. Having said that, some kilts are designed from the ground up to be worn at the pants level.

Which type of kilt are you buying?