User post: What should my Boyfriend wear?

My boyfriend of six years is in a style rut. He really enjoys and feels good wearing clothes that fit him well and make him look good. He's 5'11", kind of a bigger belly, lean legs.

On a recent trip to Payless Shoes, he noticed that 95% of the store was women's shoes and not even a whole aisle is men's. Same goes for clothing sections in most stores. And does double for clearance sections. He wants to explore new style options. But what's out there really for men?

If he were to wear a scarf he would kind of look like a hippie, gay guy. If he were to wear sports stuff, he would just look like...a sports fan; which he isn't. Put a button up collared shirt on him and he looks too preppy.

And I was thinking, yes, it IS harder for guys to develop a really good sense of fashion. Because if they dress well, most women automatically think gay right? Well, that's what he told me, haha.

He really like the way Brad Pitt dresses (minus the recently hideous goatee).
Where are good, affordable places for men to shop in the Midwest? Any style tips you could give him? Thank you all!