[FrankD]

My favorite lens for glamour is the 70-200 IS f2.8 but that's out of your reach.

So this would be my $1000,00 set:

28-75 f2.8 Tamron
135mm f2.8 Soft focus Canon
85mm 1.8 Canon

The problem with 28-75 and below 100mm is that if you want to get nice DOF or in other words only your model sharp and the rest in beautiful bokeh you need long lenses.