See, what it is, is Pentax needs a cooler-looking logo. Maybe if they went back to the early typeface, it'd be more wearable.
I don't really wear stuff with logos on it, anyway. Except maybe to bed or around the house. But I think their merchandising could probably use a little work. The current 'Big bold word PENTAX' just doesn't say much of anything. Apart from the general disinclination these days to show camera logos on straps and the like, it's just not very attractive or appealing even if you wouldn't or don't particularly mind that.
If they did a little design to make things people'd want to wear, even if they have nothing to do with the brand, that's a way to get some visibility. Just get it out there and all.
(I have a theory that Pentax ought to play up the heritage thing, send out cameras with some assortment of 'hippie strap' looking straps for promotions, and suchlike.
Wonder if we couldn't do a little viral stuff with one of those Cafepress pages and the old logo or whatnot.
For the OP, I just wouldn't worry about it. If it's the sort of thing you'd ordinarily wear, why not. If it feels a dorky or anything, it's probably not the best way for you to dress when meeting a lot of new people.