I suppose a Red Stripe T-shirt is more bro-esque than Guinness, but it's just the idea of "haha dude look beer on my shirt!" that struck me. The shorts are pretty bro. Knowing you're a die-hard sports fan, the hat is explainable.
I've worn jeans with flip flops like once, and it was because I was in a rush to go out to the deli and get something.