And why “Plaid”?
When I see the name “The Plaid Horse” I picture a red plaid stuffed horse from the 1950s, that looked sort of like this one except with a plaid body. You sat on it to watch TV.
It’s a magazine (and website) but I have no idea why it’s called that.
I’d always assumed it was a reference to the fact that plaid is so often associated with the preppy world. It’s not “official,” but if you Google preppy, I can almost guarantee the book/website will have something plaid, and lots of people from that background showed hunter/jumper way back in the day.
Now the magazine/website has changed and it’s more general stuff geared to ammies and juniors, but with an emphasis on showing hunter-jumpers, still.
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Did you know that the authors of the Official Preppy Handbook put out another book a few years ago? It’s a sequel called True Prep and was meant for all the then-young preps who are now adults dealing with nannies, second homes, jobs, etc. It’s just as funny as the first one!
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I’d read Lisa Birnbach’s college book. And there were rumors that she was the inspiration behind the family profiled in the novel The Nanny Diaries. But didn’t know there was a sequel to her handbook!
I suppose madras and monogramming will never come back, thank goodness! I was never preppy or aspired to be, but I did have a plaid skirt (worn with combat boots and fishnets in the 90s).
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Oh, it never went away, at least for people who’ve grown up wearing that sort of clothing! 
I have two madras shirts and three pairs of shorts in my closet right now, and I see monograms on dress shirts all the time, as well as on things like tote bags. I love it all!!!
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I sell apparel decorating machines (embroidery, printers, etc) People start businesses with monogramming as their main profit revenue. Monogramming will never go out of fashion.
And you know who are the biggest customers of monogramming? Equestrians !! LOL
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We had the Official Preppy Handbook at my library back in the '80s and I remember there was some talk about the differences between true preppies and yuppies. But the SE US is a long way in every way from New England and its prep schools. Back in the '60s, when we wore madras shirts and skirts and shorts I’d never even heard the words “preppy” or “yuppie.” But I did love the madras show coats with rust or canary breeches.
The other thing I picture when I see “The Plaid Horse” online is a horse covered in Baker Plaid with his rider hung all over with matching cases, or the other plaid blankets and bags and things I’ve seen in Dover’s catalog (or maybe it was State Line).
So, thank you all for the references to preppy plaids! I just don’t think of a plaid horse as a sleek shiny hunter but as a fat and fluffy cushion for toddlers to ride on when watching – well, whatever toddlers watch nowadays.
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I don’t know if it is still an affiliate, but they also did The Paisley Pony. Maybe the creator just likes fabric pattern names?
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I feel like that website started out as a sort of fashion blog for horses, reviewing saddle pads and such. Then grew into something more substantial, when many such blog sites just faded out. So kudos to them for growing and expanding.
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It’s a magazine that’s distributed at hunter/jumper shows and now has a digital presence as well. No idea where the name came from. Piper Klemm took over in the mid 2010s, I think?
Their Plaid Horse Adult Amateur Lounge on FB is really great - fun, helpful, supportive.
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Ha! Well, at very least, that confirms my free association of all things preppy, plaid, and horse!
@rockonxox Isn’t paisley also a preppy-associated fabric, along the lines of Lilly Pulitzer wrap dresses?
As the child of relatively recent immigrants, reading The Preppy Handbook was like reading a field guide to a strange and exotic way of life.
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It was for me, too, and my most recent immigrant-ancestors came over ca 1890-ish. 
Back when I was growing up, paisley was about as far as one could get from preppy style. It was hippie or quasi-hippie fabric, or little-old-lady fabric.
I love it.
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Ah prep. I was a young adult when “prep” was being marketed to high school kids in the 1980s and it made no sense back then on the Canadian West Coast when I had never seen a pair of chinos. The Gap arrived late here. When I first encountered it in London I thought it was a British company.
Much later as an adult I ended up in grad school on the US East Coast and saw the general style in its natural habitat. Simple t shirts shirts chinos and jeans on the daily with the potential to really scrub up well for special events… Merging in a lot of ways with the perennial dressed down chino look of rich techies.
That said there’s a whole subgenre of very young “fashion influencers” on Youtube, none of them WASP, earnestly referring to the Preppie Handbook to define “the Old Money Aesthetic.” Main takeaway: wealthy people aren’t generally running around in head to toe logos and diamonds in daily life. I suppose this is news to a lot of kids that only have TV and red carpet videos as reference points, and have been marketed" “luxury glam” by corporations like the Kardashians.
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Yes, I sort of think of it as the Vineyard Vines aesthetic (a “traditional preppy” company that is relatively new, but sells the image, versus the decaying L.L. Bean and Brooks Brothers wardrobe celebrated in the handbook).
This is what I meant by paisley being a preppy pattern. Hideous, yet a classic prep brand. Which I guess is part of the point–only someone with money can get away with it… https://www.lillypulitzer.com/kristen-swing-dress/002262.html?dwvar_002262_color=4411IX
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Paisley brings to mind 1970 hippies looks and grandmas old couch - muted and warmer tones. I don’t think I’ve ever associated paisley with being a preppy pattern. Now that you mention it though… Talbots has a ton of bright colored paisley and I would peg them as being quite preppy.
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Without evidence I thought that the Plaid Horse referred to Baker plaid. Many years ago, a Baker plaid horse blanket was the height of rich equine fashion.
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I love your imagery of a fashion “in its natural habitat.”
I’m also interested that you call these trousers chinos. Yes, I have seen them called that in books.
Where I live we call them khakis*. Because they invariably are.
Khakis with a short a, not “cockies” as in Britain.
Way back in history chinos were always khaki colored, but khaki is a color and can refer to anything with that color (ie: khaki skirt, khaki blouse, khaki trousers, etc). Chinos today are in many many different color options. Chino is the style, khaki is the color.
