It's basically walking. Confidently. And in a proud manner. Most often accompanied by EXPLOSIONS happening behind as if it won't hurt you. Check out Bad Blood anf every Power Rangers episode. Those two videos define "Walking like a boss". Optional: Wearing eyeglasses. This is another form of being a "T H U G". A walk that make people STARE at you and you embrace the moment by walking continuously...LIKE A BOSS!