I think the upper Aero Hercules and lower SB/AL Spiegel illustrates the point @Sloan1874 was trying to make. One can definitely see the similarity between the two patterns.
I would say the Seabiscuit and the Grizzly because they're really unique. Also the Sunburst.
Cafe Racer and Maxwell. The Highwayman is definitely the most 'useful' to me, though.
For some reason I could never get on with the Mandarin style collar on a classic cafe racer design. I had one (not an Aero) years ago, and sold it for that reason. Course, I love to wear a leather jacket with collar and tie - and waistcoat, if I can - a la Howard Hughes; I think a collared jacket is just better suited to going with a tie.
Even still, every so often I see a classic cafe racer, more cut like the Aero Board Racer, and I do wonder... Possibly one of those styles I'd buy on the right used deal, but won't gravitate towards 'new'.
I don't wear leather jackets with a shirt and tie unless it's a long one over a suit (black Stockman) and it's raining six-nil. For me, a cafe racer is best worn with a plain long sleeve t-shirt (nothing collared). I also think that mine worked best when I had lost weight and had a thinner neck and face. More 'roomy' cuts definitely work better than a cafe racer when I am more 'generous' of face.
If I had to limit myself to one Aero jacket, it would be the highwayman with the bootlegger a close second in CXL horse of course.
My current is the Barnstormer. No idea when I'd ever wear it, but I honestly think about it during both my waking and sleeping hours. Now that they make it with the detachable belt, even better.