I am a bit overweight and concerned about where the belt will sit around my waist. Is there a special way to measure to accommodate a belly?

No need to measure differently please follow the guide on our measuring page.  We have clients of all shapes and sizes; our larger gents tend to wear their belt just under the belly.  Although the edges are completely smooth we do offer liners if required to cushion the edges – sometimes clients use this for a minimal amount of time whilst adjusting to their belt.