Horrors!
Yes - I might buy the same custom belt in 2 different sizes.
Then I can wear which ever one fits me that day.
One problem is that a lot of times the third hole fits in the morning before I go to work but then after I get to work I need to tighten the belt to the fourth hole (I guess after initial settling and stretching of the clothes and belt). A better fit might be a new strap with a new hole that measures between the distance of the third and fourth holes.
In a previous post to this thread, Cary Grant mentioned that he has a Tumi belt and the strap hasn't shown much wear. If this is the case then what characteristics of leather belt straps will make the strap less susceptible to creasing (or showing creasing).
You're taking me seriously! I didn't really mean for you to follow that advice. It was tongue in cheek, actually.
Now, as for dealing with your problem seriously. I find that to be somewhat of an issue, but I choose to ignore it. There is very little likelihood that anyone but you will notice, really, as has been said above. If, however, it bothers you all that much, you might try looking for the style of buckle that runs the end of the belt underneath, with a knob to insert in the holes. That is not going to make a crease. They're called "sliders," and here's a sterling silver one by Tiffany that has a nice retro look: