/r/malefashionadvice might help you out some. I've been lurking there for a while, and for so many people it's not that they're ugly -- they're just used to wearing ill-fitting clothes that do not suit their body and face type.
I also lurk there. I will say they're a little too picky sometimes on what is and is not acceptable fashion, but they're great for teaching what good-fitting clothing looks like, as well as matching up clothes to create a style. Especially for someone who is not overweight, clothes with a proper fit can make a dramatic, huge difference in appearance.
Every time I look at that subreddit, I feel like a slob for what I wear.
Also, get a good hair cut. Pop for an appointment where you consult with a high end stylist. A good stylist really does know what they're doing. After that, once the style has been determined, you can have a less expensive haircutter simply maintain that style.
Speaking of stereotyping, the idea of taking fashion advice from <i>reddit</i> cracks me up. I'm sure it's probably fine and has some good things, but... you know, reddit.
