I hadn’t realized that you are related to Steve Bannon 
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Yes to being “fashion minded” for years now (shoes, outfits, hair). He may call it more of a grunge look, I call it the more current trend name. 
I was just coming on here to day, look at Baltimore for people who are still dressing preppy (even if they are not Ivy Leaguers or even that wealthy). It’s the preppiest city I have seen - and the fact that a huge percent of folks send their kids to private prep schools is part of that.
In Baltimore when you ask “Where did you go to school?” They are actually asking where did you go to HIGH SCHOOL, not college.
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In HI, people also often refer to where they went to HS, even though they may have college & professional degrees. It’s funny to me, but many of the friendships I have are from where I attended middle school. D and S both have close friends still that were in HS with them. My siblings do as well. I haven’t kept in touch with those I went to college or grad school—S & D are doing a better job of keeping in touch with their college buddies.
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Could it be that both Baltimore and the state of Hawaii have a high percentage of students in private schools, so that may be a more interesting aspect of someone (or at least their parents’ preferences and choices)?
Calvert Hall
Baltimore was one of the only major cities that didn’t have busing in the '70s because almost everyone was in private school. And you go where your father went (girls go where their sisters or aunts went).
Except Luigi Mangione. He went to Gilman because his grandfather became filthy rich.
But what did they WEAR? Isn’t that what we’re talking about?
Both of the more prestigious private schools in our state started dress codes. Boys HAD to wear collared shirts or hoodies. S opted for hoodies because he wasn’t a fan of collars. Girls also had a bunch of rules and you always had to wear footwear — sometimes D would end up in my way too big sports shoes when she got in the car barefoot! Haha! My kids definitely didn’t go for preppy.
At least back in the day, footwear was optional at the lower school of one of the top private schools there, with slippahs common in the upper school.
Living in a region with five seasons- summer, fall, winter, mud, and spring, it is hilarious to me that a kid would consider footwear optional! Pavements too hot in the summer. Too many leaves and pine needles in the fall (yes, they fall off), snow or slush or ice in the winter, mud season is its own hell, and spring has various invasive lantern flies, poison ivy growing in the cracks of the sidewalk or by the side of every street.
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I wore my cute madras blazer today (lunch out in an airconditioned restaurant), and got several nice compliments on it.
All I need now is a new pair of Bass Weejuns.
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Oh my brothers had to wear button down shirts (just one at a time), ties, and jackets to school. The preppy clothes were just for looking good on weekends. They played on sports teams and had to wear jackets and ties to games too and then put on their uniforms when they got there.
Taylor Swift sparked a run on these a few years ago. 
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One of my most prized possessions from my preppy era was the ubiquitous Bermuda bag with changeable covers. From Papagallo of course.
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Whale pants—still see guys wearing them.
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Frat boys been wearing this stuff in the South since the 80s at least. I live in a college town and the frat boys today and all along have been interchangeable with the frat boys of the 80s. The sorority girls change their trends, but the boys are always always always khaki short, topsiders, button downs. Madras was never a big thing for boys in this area even in the 80s. When I was in school preppy was very much a thing and I knew girls who had madras shorts, but usually in more pastel colors. And always add-a-bead necklaces and the purses with the wooden handles and boat shoes.
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The more faded the Nantucket Reds, the better!!
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I’m finding all the discussion of preppy clothing during college interesting. My college the style was more granola. Birkenstocks, cotton smocked blouses and those surfer hooded jackets that came from Mexico.
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