Wearing your clothes the wrong way was popular throughout the entire 90s decade.
First, there was the Kris Kross thing of wearing an entire backwards outfit.
That was truly stupid. Nuff said. The backwards baseball hat is still a viable option in my opinion, but there's good reason to wear your jeans, buttoned shirts and overalls in the prescribed manner.
Next up we saw overalls with one strap down. If I say one strap up, would that make this post more optimistic? This was also the time to wear your backpack over one shoulder only. If you wore it over both shoulders, you were a lame-wad.
Finally, towards the end of the decade, there was this phenomenon called "looking like a huge moron by wearing a visor upside down and/or backwards". I dislike it so much I won't even include a photo. So terrible!