Misty Water Colored Memories ...
 

The preferred pant color with the "in crowd" was black (kind of like the more modern belt versus no belt debates), even though IAABO allowed us to wear black or blue pants. I did wear blue pants once when I forgot to pack my black officials pants in my bag, and happened to have worn blue pants to my day job that day. The blue pants actually looked better with the gray jersey with blue piping than the black pants. But I wanted to be one of the "cool" guys.

I Cry About It Every Night ...
 

I had the same problem. I wanted to be like one of the "cool" guys and use a Smitty, but I kept on breaking the little loop.

Best loop replacement is a small black rubber grommet sewn on with heavy black thread. The elasticity of the rubber keeps the smitty from breaking the threads.

There were two different length smittys. A shorter one for zippered shirts since the point of attachment was higher (at the top of the zipper) and a longer one meant to reach the the loop at the bottom of the V. Sounds like you have the shorter one (or you have a really long neck).

Uh-oh.....

Actually, that sounds relatively new. I still wear my Springfield YMCA sweater that was given to me by Dr. Naismith to games. I also carry an extra peach basket in my buggy.

They come in different lengths.