I made a duplicate of a vest my office gave out, embroidered logo and all, dressed a small bear to look like my boss, and made a golf bag out of a toilet paper roll and some vinyl. I did the clubs with a Dremel. He got the bear for Christmas, and his wife kept wanting to know where I got the golf bag. (He collects bears)
The other weirdie was a drool bib. The boss used to eye the college students who walked by, and I threatened him with a drool bib. I cartooned his face, digitized and embroidered it. That was another Xmas present. He loved both.