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I had a flashback to a summer trip (in high school?) to camp in Cape Cod. Dad and I went to church, and gosh it seemed like just about everybody (members and manyy visitors) were wearing LaCoste polo shirts… in a rainbow of colors.
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And what’s wrong with this look??? 
I work at an all-boys school. I see about 500 boys dressed just like this every day. This is standard every day once the weather gets warm.
Of course, being boys, they have to get competitive about this. Some will scour thrift stores to find an original 1970’s madras blazer - and then pair it with (un)matching madras shorts. It is quite a look.
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I thought that was standard boarding school attire, but it most definitely was not, at his school anyway. Most of the boys couldn’t be bothered to find something clean and unwrinkled to pair with their flip-flops and hoodies. Even in the snow. Until graduation, there wasn’t a tie or jacket in sight. When a tee shirt became too offensive, they simply bought another one from the school store. Problem solved.
Nor mine
And shorts. 
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Of course. And, as we’ve mentioned several times on the prep forum, the ingenuity of boys running in the rain with their laptops over their heads as makeshift umbrellas because their actual umbrellas remained in their rooms for use as light sabres. And the wrinkled clothing never saw an iron because the only one in the dorm was used as a panini press.
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Wait, didn’t you go to UMich? I know a lot of UMich grads, but none wore preppy clothes. Jeans, tees, sweatshirts … no twin sets or pearls. Did you feel like a southerner (maybe easterner?) out of water?
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Fun thread. I read The Official Preppy Handbook when it came out, when I was 10, and I loved it. Got the joke but also genuinely appreciated the style and the ethos of casual prosperity. I’ve been partial to button-downs, khakis and camp moccasins ever since, somewhat distinctive for a Black kid from NYC. My wife, who grew up on Cape Cod, leans preppy in a lot of her dressing but isn’t strict about it. Our 24-year-old daughter and 21-year-old son also mix in the occasional bit of preppy style, especially our son, who joins me in playing golf and tennis.
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My folks and 2 sisters went to U of MI but aren’t preppy. Oh well! They are very aware of appearances & clothes especially tho.
When I was at Michigan, the Annie Hall look was in. The Martha Cook and Stockwell girls, though, were prepped to the nines. I didn’t have any money, so it was jeans and Michigan tees and sweats for me. I fit right in with the Downriver rats. My refinement came later when we Yuppies were all dressing for success and pursuing:
Good times.
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The preppy look started hitting my small midwestern university in the mid/late '70’s when I was a student. The guy I was dating at the time was practically a poster boy for the look. Clear memories of both the Preppy handbook and Dress for Success ( H and I owned a copy and I owned a copy of the Women’s Dress for Success book which came out a few years later).
During S’s HS years (around 2012/2013) the preppy “Nantucket Reds” were a fad at his HS. S wore a lot of Vineyard Vines in those days and was voted “preppiest”. Now he cringes at the very idea of wearing a polo.
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I can assure you that back in the day people did, in fact, dress this way at the Ivies (and in affluent towns throughout New England).
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Old money Yankees (i.e. frugal folk) still dress this way although the Nantucket reds and khakis are often threadbare.
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In literally the same clothes they bought in 1980.
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Where I grew up in the south preppy was definitely not in. It was big hair, lots of makeup, high heels and tight jeans when I was in HS
I had a pair of madras shorts in the late 80’s that I adored!
My sister bartended at a bar in Providence that was listed in the preppy handbook as a place absolutely to not be seen
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My brothers went to hs in Towson, MD, one of the top 20 towns listed in the Preppy Handbook. One brother constantly wore 3 button down shirts - at the same time. He’s take them off over his head and dump them , all together, in the laundry. Drove my mother crazy. She claimed the middle shirt wasn’t dirty as it didn’t touch skin or the outside world so he should wear it again before putting it in the laundry.
We’d get the LLBean catalog and my mother would tell us to mark what we wanted for Christmas with our names on the items. Well, of course we started marking the ugliest stuff and putting siblings’ names on them. My mother would say “I can’t believe Robby likes this, but if it is what he wants…” (cord pants with lobsters embroidered on them, a lavender sweater) It took her a while to figure out what we were all doing and that her Christmas shopping plans were ruined.
The first college my daughter looked at was Presbyterian college in SC (2013). We toured and then she had an appointment with admissions. The girl (a recent grad) was sitting there in a twin set with pearls like it was 1954. It was 195 degrees that day (I swear). We were all sweaty and gross but Miss Twin Set was cool as a cucumber in full make up and the two sweaters. Gee, not the school for us.
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Meanwhile, my frat boy son dresses like a slavic f boy most of the time (including rhinestone/studded belt). He loves buying resale clothes.
Meanwhile, I like splashes of loud color or obnoxious prints when I have to get into college professor presentation mode.
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He’s just One Wild and Crazy Guy
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Bonus points are issued only if he adopted the look before Heated Rivalry. Now it’s mainstream.
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I think I still have my 1980 copy of The Preppy Handbook. My wealthy NJ suburb hs (class of 1980) was pretty preppy as was my small liberal arts college. I still lean toward preppy as my preferred look.
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