An Age Divide in People's Opinions About Butches' Clothing Choices?

A few weeks ago I wrote this article recounting my pseudo-gender-conforming job search.  Shortly thereafter, a butch superstar six or seven years ahead of me in my field reached out about the article, and we ended up having coffee and chatting about her experiences.  Not only was she even more awesome than I’d hoped, but she had interesting theories about butch clothing selection that are way too interesting not to share.

Said superstar proposed the following:

• There's a big divide around age 50 or so.  The divide isn't due to age, but to generation (that is, 45-year-olds will not suddenly change their minds in 5 years).  People, including lesbians, 50 and older tend to believe that butchy lesbians should wear gender conforming clothing (not heels and lipstick, but at least women’s suits and a pair of earrings).  By "should," I'm not talking about a moral imperative, but about a strategic decision.  People 50 and younger, on the other hand, think butchy lesbians should wear men's clothing, if they so desire, and believe that nothing bad is likely to come of it.
  
• People who are liable to discriminate against me because I look like a big ol' dyke won't be less likely to discriminate against me just because I've a small effort at gender conformity.
• If I "look like a lesbian" and I'm wearing men's clothing, I will at least be recognizable as a type—a butch dyke they can put in a particular box.  They'll like me or they won't, but at least they'll know where to file me.  If I'm wearing, say, a string of pearls but still "look like a [butch] lesbian," it's a little harder to stick me in a box, and the inability to stick others in boxes makes people uncomfortable. 
  

The bottom line is that Superstar says to go for a men's suit next time—at least, it worked for her.  So maybe I will.  Or maybe I'll go back and forth, since I like both men's and women's suits that are relatively gender-neutral in appearance (e.g., no cutesy buttons for women's suits, no mega-structured shoulders for men's suits).  But I do like wearing ties, which tend to look better with men's suits.  Superstar had no major opinion on ties, since she doesn't wear them herself, but since they are THE quintessential "men's" professional clothing item, maybe a tie would be more likely to be looked on unfavorably by prospective hirers.

What do you think about Superstar’s theories?  Let's unscientifically test one of them!  Click here to take a SUPER-quick 2-question quiz.  I'll post the results this weekend.