The picture on the left represents my clothing style best. Hair is currently on the longer side since I wanted to try growing it out but am not sure what to do. Any advice is welcome
you may get additional insight in fashion-discussionHair💈✂ however shampooing less and conditioning more often can yield more waves, especially if you're also using a texturizer or mousse (while your hair is damp)
a better idea is to show the example pictures to a hairstylist and ask how to achieve that on your head - they might suggest adding layers for movement or some other styling/care method
everything zeometer said, and also learning out to properly treat your hair, i.e learning how to dry it properly, sleeping with a bonnet. right now your hair still looks too short to acheive the look you are going for, but imo you could rock that look, or even even longer hair then that could look very cool, think hipster man bun, around that length.