This is why, if I score some distinctive-looking item of clothing at the annual donation/discard giveaway after Commencement, I wait three years before wearing it on campus. 
I’m not at all ashamed of scavenging good garments for free that nobody else wants, especially since I’m good at mending and alterations so they don’t look like hand-me-downs. But I don’t want to potentially freak out some prior-owner student who still thinks of secondhand clothing as exclusively for “poor people”.
Not me, though. I am very comfortable with my vow from a few years back to acquire only clothing that is either secondhand or made by myself (with a few, and shrinking, exceptions for stuff like underwear and technical gear). Never had a bedbug or moth problem with thrifted garments either, although tbf I am pretty scrupulous about checking and pre-cleaning.
That’s my take too, and why I do it. (Recent brag post about the advantages of overseas thrift stores to avoid the personal and environmental burdens of luggage during long-term travel.)
However, I hear what some folks are saying about not liking the inefficiency of hit-and-miss thrift shopping, or having more specialized requirements that thrift stores aren’t useful for. In those circumstances, thrift shopping is more trouble than it’s worth.
I’m lucky in hitting about the middle of the bell curve in most size and style categories (especially foot-wise: about half the women’s footwear in a thrift shop seems to be in my size), and also in having the abovementioned mending and alteration skills so I don’t have to depend on the serendipity of finding a perfect fit in perfect condition.