I would echo the sentiments of those who wear all the gear, all the time. I plan on upgrading my armor, even going so far as to getting chest protection gear to go under my jacket.
That said, I'm thinking that the real spirit of your question, coming from someone as yourself with a Harley background, was: "will I look dorky with my Harley-type gear on a scooter?" If that's what you meant, then I'd say yes. Nothing irks me more than the handful of times I've seen someone with "the pirate outfit" i.e. leather vest with a million club patches, do-rag/beret, streaming fringes/tassels, etc....on a maxi-scooter! It just screams "I would really rather be on a Harley like the rest of these guys I'm riding with, but I just settled on this dang scooter 'cause it's all I could afford [or I can't throw a leg over, etc]". Maybe because I just see scoots & cruisers as polar opposites, that's all.
Yes, there are different gear styles that cater to the type of bike one rides, and I wouldn't dogmatically say you have to stay within a specific one, especially since maxi-scooter riders technically don't have a specific "look" or gear style like Vespa riders, sport-bikers, cruiser riders, sport tourers, and adventure/dual sport types do. I tend to buy good quality, solid, highly protective gear that just so happens to fall in the latter two aforementioned categories' looks, maybe because I personally see maxi-scooters as "touring bikes" more along the lines of a Goldwing, BMW or Concours. But that's just me, since I like that look.
Just wear good gear above all else. Best comment on here, Buffalo said, a scooter is a motorcycle and you can't think you'll look foolish on it with motorbike gear, opting to ride around like "Roman Holiday" lest you end up real hurt.
Anyway, all this is on the supposition that what you were asking about was revolving around "scooter fashion". If it wasn't, then disregard this whole post.:wink