Digital Art Why do I keep creating these unbelievably weird and strange things

Someone please tell me how to make a stroke border anti-aliased if possible, or simply an easier method of achieving such a border without all of the messy shenanigans? It is my biggest pet peeve (along with Patchouli needing to blend into the background more so).
Comments and critique please. I do not do this often so I must sharpen my skills.