When you hoop a beanie, mark where you want the monogram to be (Purple Pin) then flip the beanie inside out. Pin the beanie to some cut away backing (Yellow Pin) so it doesn’t move while sewing. Don’t stretch the beanie out while hooping. Let it maintain it finished state. If you stretch it out, it will look smashed when you are finished the job.
Black backing would be nice on a black hat. Solvy is absolutely necessary.
The top of the purple pin indicates the top of the logo.