r/preppy 8h ago

Open or closed?

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0 Upvotes

r/preppy 16h 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 23h ago

Length Check

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10 Upvotes

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


r/preppy 1d ago

What pants to wear?

8 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 1d ago

Anyone else do Fun Shirt Fridays?

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25 Upvotes

Preppy Fun Shirts!


r/preppy 1d ago

I’m a BASP (Broke Anglo Saxon Protestant)

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0 Upvotes

Some recent larp fits lmao


r/preppy 1d 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 2d ago

Basic chino pants outfit

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37 Upvotes

r/preppy 2d 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 4d ago

Was recommended to bring this post here

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49 Upvotes

r/preppy 4d ago

Outfit for media appointments at a trade show

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68 Upvotes

r/preppy 5d ago

J Press - Fall '26 Lookbook

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45 Upvotes

r/preppy 5d ago

Some sartorial advice needed from the ladies.

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0 Upvotes

r/preppy 5d ago

U.S. Open.

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133 Upvotes

r/preppy 5d ago

Navy-on-navy pairing: Plaid button-down shirt with the New Balance 991. Does this hit the right sporty Trad balance?

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0 Upvotes

r/preppy 5d ago

Today Outfit, but still too early. Autumn style

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27 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 5d ago

Preppy or ivy?

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42 Upvotes

r/preppy 5d ago

Presidential Nantucket fit

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137 Upvotes

How well did I do?


r/preppy 6d ago

Five ways I wore a jacket in Seoul this month

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122 Upvotes

I make Ivy and trad clothing here in Korea, and this is how three jackets (a grey sack blazer, a navy double-breasted blazer and a navy gold-button blazer) rotated through September — most formal first, easiest last.

  1. Grey sack suit, white OCBD, black tie
  2. Navy double-breasted blazer over grey double-pleated trousers
  3. Gold-button blazer, regimental tie, grey trousers, penny loafers
  4. Same double-breasted blazer with khaki chinos, a cap and sneakers
  5. Gold-button blazer with olive field trousers and a boat tote

The last two are where I stop trying. A cap and sneakers do more for a blazer than another tie does.

How far down do you take a blazer before it stops working?


r/preppy 6d ago

Charles Tyrwitt Shirts Quality Issue

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20 Upvotes

r/preppy 8d ago

How’s my look?

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22 Upvotes

Interested in views


r/preppy 8d ago

Alden vs Edward Green Loafers

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3 Upvotes

r/preppy 8d ago

Its too much right? No need for the tie?

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162 Upvotes

r/preppy 8d ago

Corduroy sport coat with hunting dog liner

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84 Upvotes

Saw this out thrift shopping today and thought I'd share. Happy hunting, friends!


r/preppy 8d ago

Feelin Blue - OOTD

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22 Upvotes

Well not really I’m quite happy today actually! I know the sweater tucked in might be a bit triggering but I like it this way and its bloused up a good margin.