When it comes to casual wear – especially things like T-shirts and henleys – the proper fit means you can get away with extremes in other departments, namely the overall condition of the material.
Check out how beat up this shirt and jeans are. A work shirt is supposed to be worked in so don’t be afraid of beating the crap out of your clothing. This holds even more true if you’re buying it cheap and know it can be replaced quickly and easily. This guy looks like he just wiped the grease off his hands and joined his buddies at the pool hall. If there’s a hottie there, he’s still good to approach because the fit of the shirt means its rattiness goes from being a con into a pro.
I’ve said it before, and I’ll say it again, and again, and again – Fit. Is. King.