Looking at the picture below, it's easy to see why the perimeter of a polygon inscribed in a circle is an underestimation of the circle's perimeter. This follows from the triangle inequality: Any side (say $AB$) of the polygon is shorter than the circular arc with the same endpoints ($\stackrel{\frown}{AB}$). Summing all these inequalities shows the perimeter of the inscribed polygon is indeed smaller than that of the circle.
I'm wondering if there is proof that the perimeter of a circumscribed polygon always overestimates the perimeter of the circle, which is as simple as that of the inscribed polygon case. Thanks!

Pick a point $F$ on one of the arcs of the circle, let us say it's on arc that faces $C$ in your circumscribed quadrilateral. Construct a line segment $GFH$ with $G$ on $BC$ and $H$ on $CD$, tangent to the circle at $F$. $GFH$,being a straight segment, is shorter than $GC+CH$, so the circumscribed pentagon $ABGHD$ has less perimeter than the quadrilateral $ABCD$. Keep adding sides to the polygon by drawing additional tangents and the polygon perimeters will constitute a strictly monotonic decreasing sequence. So the terms of that sequence must be greater than the limiting value which is the circumference of the circle.