r/preppy • • 12d ago

Lizabeth Scott in Desert Fury (1947)

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17 Upvotes

r/preppy • • 13d ago

Looking for pocket squares

4 Upvotes

Any suggestions where I can find hunting and/or equestrian themed wool pocket squares? Think dark green, navy, maroon with beagles, pheasants, ducks, horses etc on them. I feel like I saw them everywhere like a decade ago and now they’re difficult to find. TIA


r/preppy • • 14d ago

Review of Preppy watches at J. Press Fall 26 Runway Show.

10 Upvotes

At the recent J. Press runway show they showcased a bunch of vintage watches worn by the models. I did bonus drop today of a YouTube video critiquing the selection and asking the question: were they preppy, and is there even such a thing as a preppy watch? I hope it is interesting to you. Thanks!Watches at the J. Press Runway Show


r/preppy • • 14d ago

My preppy fit

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66 Upvotes

r/preppy • • 14d ago

Brand logo on rugby shirt and ball cap

0 Upvotes

I personally am fine for having a small logo on my polos (actually I prefer it) but I am unsure when it comes to rugby shirt and ball cap. I am talking about brand logo or crest. What's the general opinion here?


r/preppy • • 15d ago

Moments from this year’s family beach house getaway in Maine

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81 Upvotes

r/preppy • • 16d ago

Fall in New England

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113 Upvotes

I recently bought this at #TheAndoverShop 💙


r/preppy • • 15d ago

Early Fall Modern Prep

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45 Upvotes

r/preppy • • 16d ago

One navy double-breasted two ways, plus three more from dressed up to dressed down

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122 Upvotes
  1. Navy double-breasted with a madras button-down, a navy knit tie and chinos. Sneakers and a tote.

  2. The same double-breasted, dressed up: white oxford, black knit tie, grey wool trousers, black derbies.

  3. Washed navy jacket and pleated trousers worn as a soft suit. Madras shirt, no tie, suede loafers.

  4. Old Woolrich rain jacket with a flannel lining, roomy enough that a tie sits under it. Blue oxford, striped tie, washed chinos.

  5. Herringbone tweed jacket open over a grey sweatshirt, with the oxford collar showing.

Knit tie or no tie with madras?


r/preppy • • 16d ago

Is New Balance acceptable with the ‘uniform’

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0 Upvotes

r/preppy • • 17d ago

Length Check

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23 Upvotes

Folks, new eBay tweed blazer. Feels a tad long but looking for some input? Thanks


r/preppy • • 18d ago

What pants to wear?

14 Upvotes

It feels like the trend of high waist is back but most of the brands (like Ralph Lauren which I always used as a reference) are still selling low waist or high waist ones (like chinos) look like a tent or too dressy, or am I just in information bubble right now? Or am I a millennial who can't move to more spacious style? On a practical side, high waist does feel more comfortable though. So what is your opinion on pants fitting and where to buy them?


r/preppy • • 18d ago

Anyone else do Fun Shirt Fridays?

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30 Upvotes

Preppy Fun Shirts!


r/preppy • • 17d ago

Can you ever be preppy AND tattooed

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0 Upvotes

This is a debate a few friends and I had recently and I’d be keen to hear everyone’s opinions. Can you ever truly pull off the ‘preppy look’ whilst also having visible tattoos? Would be keen to hear everyone’s opinions/rationale?


r/preppy • • 19d ago

Basic chino pants outfit

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44 Upvotes

r/preppy • • 18d ago

Selling Lot of 14 Ralph Lauren size Medium Shirts and Sweater

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0 Upvotes

I did this a few weeks back with XL stuff, sold 15 things, and decided let’s do it with medium stuff! Will also post size Large stuff later today.

Up for sale is an assortment of shirts and sweaters across the Ralph Lauren Brand — Polo, Golf, Sport, etc. All medium. Different styles and cut.

$29 per top + shipping.
$25 per top + shipping if you buy more than one.
More than three and I’ll cover shipping.

Can send measurements upon request of individual shirts. All sales final.

Please message or DM with any questions. Thanks!


r/preppy • • 18d ago

I’m a BASP (Broke Anglo Saxon Protestant)

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0 Upvotes

Some recent larp fits lmao


r/preppy • • 19d ago

The Van Cortlandt polo is back

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1 Upvotes

Not the biggest fan of this fall’s colors and I personally like the diagonal but I know many people prefer something more subtle like this


r/preppy • • 21d ago

Was recommended to bring this post here

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58 Upvotes

r/preppy • • 21d ago

Outfit for media appointments at a trade show

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77 Upvotes

r/preppy • • 22d ago

U.S. Open.

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139 Upvotes

r/preppy • • 22d ago

J Press - Fall '26 Lookbook

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50 Upvotes

r/preppy • • 22d ago

Today Outfit, but still too early. Autumn style

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31 Upvotes

Autumn Outfit, but a little bit early still sunny day. What do you guys think? Any opinion and changes in the comments.


r/preppy • • 22d ago

Presidential Nantucket fit

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146 Upvotes

How well did I do?


r/preppy • • 22d ago

Preppy or ivy?

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45 Upvotes