Looking nice man!
Yeah, you got it. Not really a ton of options when dealing with a hat: Push the brim up or have the model tilt the chin up to help light get under, but that changes the whole mood. You could use a disk reflector/bead board/show card on the ground to bounce light back up under, but with a tight space setup like the one here, you might not have the angle to do so. If you had another light you could shoot it into the wall behind the camera and it would act as a soft fill to just lift the shadows under the brim while leaving your softbox to set the mood. But yeah, lowering the light is the quickest and most effective.
You can also see that black felt, black velvet anything like that absolutely absorbs light like a blackhole. You did great with the hat/hair light on camera left to show the shape of the hat. That and the leather band showing up from the key light does justice to the hat.
It works better with an umbrella/softlighter, but you can try a little trick with the softbox. Instead of pointing the light directly at her face there, rotate the light a little to the left. It will feel like the middle of the softbox is aimed at a point just in front of her nose. It'll help "wrap" the light around her face a little and illuminate the other side. If your softbox is rectangular, you can rotate it so the long axis is horizontal and it'll help wrap as well. Full body that won't work, but since it's a tight portrait, it should be fine. Give it a shot, if you have questions, lemme know.
You should get a model and start shooting a real person - it definitely ups the stakes as you're now watching the hair, the makeup, the posing and trying to effectively communicate with the model while capturing the moments.
Looking good man, keep it up.