In 2000, our friends dressed up with us. We were Jack and Sally from Tim Burton's The Nightmare Before Christmas. My best friend Susie and her then-boyfriend now-husband Chad were a generic Medieval couple, and my then-roommate Nikki was Mimi from the Drew Carey show.
Jon completely made his costume from scratch and I completely made mine from scratch as well. I bought 5 or 6 old shirts from the Goodwill, cut them up, and hand-stitched them together. I bought a blonde wig and dyed it red, leaving the dye in so it got stiff and crusty, because Sally's hair is basically one mass with no individual hairs. Jon made his mask with a balloon, some Celluclay, and some acrylic paint. He bought a black shirt and pants and painted them with white stripes. I bought a white shirt and pants and hand-stitched black sutures into them. All in all, a great result.
Sadly to say, I think Susie and Chad bought their costumes that year. In coming years their costumes got much better, don't worry. And they made them and everything. Nikki bought all of the components of her costume and padded it all up with a couple of pillows. It was a truly frightening costume, I must say.