I'd loosen up your spacing now, it's still a bit hard to read.
On the 1-2 one, make the phrase in two straight lines, stacked, with only "The Class Of" in the script.
Then make the pennant be the dash.
I graduated in 1980 when Pink Floyd's "The Wall" (we don't need no education) was the big hit.
The father of one of my fellow students was a brick layer by trade.
That kid and his buddies literally built a brick wall in front of the main door to the school overnight before the last day of senior year. It set up nicely by morning. The principal was not pleased.