Now, back to the subject at hand:
Now, were you to see me, dressed the way I am, with the haircut I have, you could come to a number of conclusions:
He is yeshivish
He is a modern person
Now, those may be two very extreme viewpoints, but you can see how my definition of Yeshivish, may be somewhat different than yours.
In closing, Subjective opinions are just that. They are not fact, but who does the saying, coupled with what that person has shown his or her hashkofoh to be on prior topics, should give you an idea of what yardstick was used to make the statement that was made.
And for the record, I WORE A BASEBALL CAP AND 3 BUTTON POLO yesterday, but changed from head to before going to maariv (so there!)