+1  A: 

You can have transparent labels in .NET.
Check out this article on CodeProject on How to Use Transparent Images and Labels in Windows Forms

As for you drawing problem Calibri doesn't have a native font size of 10. You can verify this in Control Panel->Fonts. The smallest native font size is 12 (on my machine at least). Change you from size to 12 and you will see it's much better.

When you don't use native font sizes somewhere under the hood Windows/.NET/GDI+ will attempt to scale the font for you. This scaling is most likely causing your problem.

ParmesanCodice
Thanks for the info, but Calibri looks fine in Word at 10 pt and still ugly in my app at 12 pt. As a truetype font, it should be able to render at any size without being ugly, like in my mockup.
Coxy
Yeah I understand your frustration. We had a similar problem with Courier New (also a true type font) in a rich text box. Did you try it at size 12? Also remember it's highly possible that Word/Photo Shop/etc are more "cleaver" at resizing fonts...
ParmesanCodice
Yeah, I did try at size 12 pt in my app. I think it must be a ClearType problem.
Coxy