I don’t know why you call it a funny t-shirt. For me, it looks damn attractive. It is that shade of gray which I normally preserve for some special outings. Cotton jerseys are cotton jerseys after all. You cannot expect the same magic from polyester material. Yes of course when you read the words Upper-Class Trailer Trash, it does invoke a fair share of humor. But I find that stylish and cool. It is a what you call something for the cool guy may be from a software background in the college. These software guys do enjoy a lot of reputation in my college!
If you are still looking for the grey trailer park shirt to match with your denim, go for the product. It is affordable and enjoys a good reputation. The photo on Amazon shows someone wearing the shirt with black jeans, which makes the matter very clear. In my view, these are for classical evening get-togethers, when you have nothing to do but speak your mind out. In case you haven’t noticed, funny people have a unique attire. It may not be something really flashy but there are some subtle indications. T-shirts, in most cases, reveal something about the mind.