The biggest point of disagreement: can you dress up an oversized tee? Regular-fit loyalists say no—it's inherently casual. Oversized fans argue it's all about how you style it. They'll point to streetwear icons who wear oversized tees with tailored trousers and dress shoes.

The truth is, it depends on the tee. A graphic tee with bold colors and a loud print is casual no matter the fit. But a solid-colored oversized tee with a subtle chest print can pass as smart-casual if you pair it with the right pieces.

The other clash is comfort. Regular-fit folks say oversized tees are too baggy, they get in the way, and they make you look smaller than you are. Oversized fans say regular tees are too restrictive and clingy. Neither is wrong—it's personal preference.