Could I pull it off?

So I'm 23 years old, and I'm sort of stuck when it comes to fashion. I'm a massage therapist, my work clothes are just yoga pants and a polo, so I don't have to worry about business suits.

I've been told I dress really well, but I'm going to need some new clothes soon, and I think I want to upgrade from t-shirts to collars. On the other hand, part of me feels that casual dress clothes on a 23 year old wouldn't look quite right. I'm at the point where I'm obviously not a teenager anymore, but still not quite an adult...

link

So what would you think if you saw a suspiciously well dressed young guy walking down the street? Should I wait another year or two before hanging up the jeans and tee's?
Updates:
+1 y
After a lot of googling (and some helpful tips here), I realize that that link is a bit over the top lol. I think I've got a better idea of what I should be looking for.
Could I pull it off?
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