1987, Steven Tyler

Steven Tyler, the fiery frontman of rock’s late ’80s heyday, was known for pushing boundaries with his music and fashion alike. However, even rock legends can have their fashion missteps, as evidenced by this eye-catching ensemble. In this daring outfit, Tyler showcased his chest while donning suspenders and a matching jacket.

While we might be inclined to overlook the revealing top, the real head-scratcher was his choice of pants. His patterned trousers were so snug that they left very little to the imagination, making one wonder how he managed to walk in them!