Every man deserves the right to dress and present himself to the world at large (and Instagram) as he see fits. You can't rely on Debbie or your Aunt Tilly forever, my dude. They don't cook your dinner every night and pack your lunch every day, do they?
Dressing is like cooking: Pay a little attention to technique, start out with the right stuff, and then don't overthink it. If you get the fit right, it's wildly easy to step your style game. Shirt that fits, nice shoes, a little pop of color, maybe a tie or a jacket. Finito! Read on and take charge.