There were more than a few Outlaw 356's at the recent Porsche Treffen at the Phoenix Club in Anaheim. Sorry I didn't get any pictures. There may be some on the web somewhere.
Most all had the 5 1/2's in the front too because I think they are supposed to emulate early sportsman road racers. That would make a major difference in the overall look. You could keep it low in the front but drop the back a little too. A little more towards handling than drag racing.
They don't usually use any bumpers at all either. You might get away with the big curved t-bars from the era, but I don't think the Cal-look T-Bars will pull it off as well.
A tuck-a-way exhaust with twin exhausts out the stock openings would be most like a Porsche. For a major effect you could fill the stock pee shooter holes and move them out to the fenders

A lot of them ran glass packs on tuned exhausts in the early 60's too.
Some of them carried the fitted luggage in the rear compartment, but you may forgo that as far as whats cool to me

Of couse you can outfit the interior like any sports or GT car, which a VW is anyway

Some had too much stuff, like fog lights, big rally badges across the hood (bonnet), Mobil oil Pegasus stickers on the front quarters etc.
It's okay to go with a satin paint job as well it seems, there was one very attractive pre-A with a semi-flat but fresh paint job that had a real clean uncluttered look.
I think if you keep it simple and purposeful, it can be pulled off.