We don't need wholesale change. A blend of modern and retro:
Keep the current colors/template for the white and black jerseys.
Untilt the pinwheel and use it, on its own, as the primary logo. No parallelogram or words. It is iconic enough on its own.
Then, use the retro lower case font and have "blazers" on the white and "portland" on the black.
We can then have 2 alternate jerseys that can be what ever. Maybe do the retro red with the underlined Portland as that was a great jersey.
the other alternate could be some new style entirely, maybe with sleeves for those who like (I personally hate the sleeve look).
That would make for a great lineup and great merchandise. The current merchandise line is just lame and boring and keeps me from spending money, something I'm sure the organization would like to change.