You can easily trace a photo in Silhouette Studio. Cleversomeday has a great tutorial on how to do this as part of her Tracing Without Tears series. I then used my Silhouette Cameo to cut out the stencil onto freezer paper, ironed it on the shirt and painted with cheap acrylic black paint.
The pattern for this fun slouchy beanie is now available in my Ravelry store! I named this hat the Elena, after my new niece. Get it here.
Font: Cheddar Jack
Font: LW Favorite