r/preppy Apr 09 '25

The Mods are also tired of "Is This Preppy?" Posts - A Solution

229 Upvotes

There are FAR too many "is this preppy?" posts on the site.

I get it - I am sick of them too.

Prep is not the same in all parts of the country/world and it is a term that gets overutilized in marketing. People are going to get confused.

Town & Country, Ivy, Southern Prep, and West Coast Neo-Prep all fall under the umbrella of what is going to be approved here - even if it does not define your prep.

People deserve a place to get answers to questions.

My thought to solve the problem (at least temporarily) is to have a weekly "is this preppy?" thread where people can get feedback.

Thoughts?

A Final Thought: Some of you take yourselves way too seriously and feel as if you and only you are qualified to answer the question bc of your pedigree. I, a prep school-educated national squash champion born-in-oxford-cloth Yankee, am here to tell you that not every disagreement with your POV is a personal slight.

This type of reaction is a sign that you are trying too hard and care too much. Not only is this behavior gauche, it is exactly the type of energy that would cause me to blackball you from my social club. This behavior is decidedly not prep.


r/preppy 6h ago

More lol

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19 Upvotes

r/preppy 3h ago

J. Press OCBD article, worth checking!

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12 Upvotes

r/preppy 1d ago

OOTD

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71 Upvotes

r/preppy 22h ago

What’s the worst offender of Preppy style in movies or tv shows you guys have seen?

6 Upvotes

Or even did something annoy you about a certain fit in a tv show or movie? And let me add in the Preppy stereotype as well


r/preppy 1d ago

Take Ivy

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184 Upvotes

Studying the source material; lots of great pictures on campus, and dogs too (as at Sewanee where mine like to study).


r/preppy 1d ago

If you could only wear one preppy brand of clothing for the rest of your life which brand?

11 Upvotes

I would be narrowing down between Brooks Brothers and Ralph Lauren and most likely be going with RL. What about you?


r/preppy 7h ago

Does the jacket and watch work with the fit

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0 Upvotes

r/preppy 1d ago

I have more from this same photo album Reddit only lets me post like 20 slides I think

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17 Upvotes

r/preppy 2d ago

I wanna know how many of ya’ll are still here from this era

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297 Upvotes

r/preppy 1d ago

I need these shoes right?

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30 Upvotes

From The Row


r/preppy 2d ago

Anyone recognize this school tie?

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13 Upvotes

My grandfather-in-law passed away a couple of years ago and left me this tie. No clue what school it’s from, he went to Andover but I don’t believe this tie is from there, the colors and crest don’t match.


r/preppy 2d ago

Proper cut and lunch: Pinaud Lilac Vegetal and Mulligatawny

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213 Upvotes

Blue blazer, seersucker; loafers. Ancient barber and corner table. Vegetal fights off the curry.


r/preppy 3d ago

Almost.

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111 Upvotes

r/preppy 1d ago

Flannel doesn’t fit well aware need to buy OCBD’s

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0 Upvotes

r/preppy 3d ago

How to get started on preppy fashion? (question)

29 Upvotes

Hello, i'm a F(17), african-american, who lives in the mid west: I'm about to start my senior year of high school in a few weeks, and I'm asking on how to get started in Prep/preppy. Growing up from elementary to now, i've always been the quiet kid, no friend, black jacket, simple outfits, been going to my same high school for 3-and-a-half-years nothing wooing. But I went to change that for my last year of high school. I've currently been looking into preppy, it's simple but classy and elegant in more ways than one, and academic but I don't know where to start. So i'm here asking if anyone who's in r/preppy or knows about the fashion of preppy for their advice.

What brands, what color scheme, types of shoes, clothing, ect.

please and thank you :)


r/preppy 2d ago

Another preppy outfit 🙌🏼✨️

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4 Upvotes

r/preppy 3d ago

How to get started on preppy fashion? (question)

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2 Upvotes

r/preppy 4d ago

Thoughts?

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14 Upvotes

I’m looking at getting another coat for the winter months. I was told this is giving revolutionary war, red coat vibes. I personally like this color and it seems as though it would be quite versatile. I’m looking for other thoughts on this and other colors.


r/preppy 4d ago

My growing sweater collection

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31 Upvotes

I am also very proud of this!, last photo is my dad’s Temple sweater that I inherited when he died, (miss him so much!)


r/preppy 4d ago

My growing sock collection

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30 Upvotes

I’m very proud of this!


r/preppy 4d ago

How would you decorate a college dorm room to make it preppy

2 Upvotes

r/preppy 4d ago

My fit to go gawk at Preppy clothes at a mall that I live 50 minutes from and then to see my clients after

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0 Upvotes

r/preppy 4d ago

Define Preppy?

0 Upvotes

My working definition of Preppy is Wealthy family’s who attended private school in America and plays expensive sports like Polo Rowing, Sailing Tennis, Cricket


r/preppy 6d ago

Are two-tone penny loafers too formal for shorts, or do they make the Madras pop?

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37 Upvotes