If your machine will not allow you to rotate the design at 45 degrees, then you should hoop with the point of the handkerchief at the center of the bottom (the side nearest you) of the hoop.

Don't try to hoop the handkerchief. Hoop the stabilizer then baste the handkerchief down at the angle that you need. I think wss would probably be the way to go. But I haven't actually done one.

Tack a piece of scrappy fabric to the sides of the hanky to make it big enough to hoop, then stabilize and embroider as normal. The tacking stitches will pull out very easily afterwards.

You could also hoop the wss and lightly spray with adhesive spray then stick the hanky to the wss. I do this sometimes with wss but only a light coat of adhesive.

hoop up with water soluble or stitch and tear next if you can make a baste stitch around the desgin so that is sews out first on the backing. now yoiu can position the hankerchief in the baste stitch. repeat teh baste stitch to hold the material done and then sew out the design. if you cannot do a baste just around the design then print out the design in actual size again hoop up and have the design to sew in the center of the hoop.
Next position your printed design central and mark with a pen the bottom point where the hankerchief will be placed. use a childs glue stick to position and hold down the fabric in the hoop baste and sew out. hope this will help you
annie in the uk

I think sticky stablizer is the way to go on this one. Hoop your sticky first then score the area to be stitched, 'stick' your hanky to this area with the point of the hanky to the center of the bottom of the hoop and you should be ok....

when I embroider handkerchiefs, I use stickt tear away stabilizer in the hoop and just put the handkerchief on the stabilizer. It works for me,gerry