Preppy clothing

Thread for a side discussion starting in Is Prestige Still about Ivies and Rankings? - #335 by neela1

Based on June 2026 | Princeton Alumni Weekly and these images:

My wardrobe has never NOT looked like that. As @skieurope knows, I’m still wearing a twinset, pearls, and knot earrings. From the previous thread, it’s clear our son thinks I look ridiculous.

I miss Pappagallo, but thank heaven for Talbot’s.

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The following contain some images from the 1980 Preppy Handbook by Lisa Birnbach.

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I want to see who is bold enough to wear the madras blazer, button down and shorts all at the same time. :blush:

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Like imsaid on the

Like I said in the other thread. This blazer is one of my favorites!

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Show us the rest of the outfit, @thumper1! :rofl:

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Here seem to be two retailers where you can buy all of the pieces.

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I have khaki shorts and pants, and navy shorts and pants. The blazer has every imaginable color, but looks best with a hot pink or teal green tee shirt top.

No button down collars in my closet.

But if needed, I could make myself look like a page out of the Official Preppy Handbook…complete with a flip hairstyle.

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Here’s one of my favorite pics of our son. I thought he dressed like that at school every day. Sadly, no. He said it was a crew tradition to dress “ridiculously preppy” the day before the Head of the Charles regatta. At least the lobster tie got some wear.

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Oh I forgot…I have a few Vineyard Vines button up shirts in my closet…but they are not solid colors. They would look ridiculous with my madras blazer.

Try us.

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This must be one of those fashion trends which may have taken off overseas but actually no one dresses like that (unironically) in the real Ivy+ schools.

Only because the composition of the students entering the ivys has changed materially over the decades.

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The look is actually quite the rage these days in the East Asian countries. Well, except North Korea.

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I am wearing my vineyard vines quarter zip right now.

And the madras button down in the first picture. I saw an influencer wear one almost exactly like it last week. I really thought about ordering it lol.

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I would wear a madras skirt/skort/dress in a heartbeat and not give a thought to it being preppy - just being something I like (and the fabric is usually summer friendly). But absolutely NO polos for me. :slight_smile:

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Two women from my dorm/floor were models for the Preppy Handbook (maybe calendar?) - one was a high school classmate.

I began college in Fall of 1979 and this is what we wore.

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Fun! Add long socks to this look that match the tie and he’d be wearing the type of outfits my colleagues in Bemuda wear daily to the office.

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My father was a Philips Exeter alum and so I got to go to summer school there when I was in high school. I called home and he asked how it was going and I said I didn’t understand why PEAs mascot was an alligator, bc I had never seen an IZOD shirt and thought the ubiquitous gator was somehow related, lol. My roommate was planning her debutante ball, and at first I thought it was a joke…

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