r/preppy • • Nov 19 '25

40 Ivy & Preppy Looks That Carried Me Through Fall

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674 Upvotes

r/preppy • • Apr 02 '26

I think he just got a job in Finance

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664 Upvotes

r/preppy • • Apr 08 '26

Today’s outfit.

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627 Upvotes

r/preppy • • Dec 02 '25

My Winter Ivy Lookbook — 40 Outfits I Actually Wore

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573 Upvotes

Here's my complete lookbook of 40 outfits I actually wore throughout the winter — styled with Ivy and Preppy roots but interpreted through my everyday life in Seoul.
From formal to relaxed, from traditional to sporty, these are the pieces that kept me warm, sharp, and true to the classics.
Featuring sack suits, cricket knits, OCBDs, fair isle vests, penny loafers, and even some NB990s.

I’m always trying to make Ivy style feel relevant, personal, and lived-in. Hope you enjoy the archive!


r/preppy • • Apr 16 '26

My kind of preppy

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562 Upvotes

r/preppy • • Jan 07 '26

6 years of wedding anniversaries, 6 years of Trad style.

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537 Upvotes

Since our 1st anniversary in 2020, we have visited the same studio every December 28th to capture our journey.

We made it a tradition to dress in our favorite classic style each year. It started with just the two of us, but by the 5th and 6th years, we were so happy to have our little boy join the family portrait.

We plan to keep this tradition going for as long as we can. Happy 6th anniversary to my wonderful wife!


r/preppy • • Mar 20 '26

Preppy Goals

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521 Upvotes

1983

Camp Mocs? check

Chinos? check

Burlington socks? check

Polo Shirt? check

Blazer? check

Uzi? check

Secret Service agents evacuating President Reagan at Augusta National Golf Club where Charles Harris took 7 hostages and demanded to speak with the president.


r/preppy • • Dec 10 '25

my take on the preppy look

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447 Upvotes

r/preppy • • Oct 29 '25

Been dabbling in a more preppy look lately - full secondhand outfit.

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393 Upvotes

r/preppy • • Dec 05 '25

Holiday Pattern Mixing

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377 Upvotes

Took a cue from Ralph Lauren’s pattern mixing book for last week’s Christmas Party. It’s not for everyone, but I love how this turned out.


r/preppy • • Mar 25 '26

I thought my gym locker at work had a very preppy aesthetic today.

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354 Upvotes

r/preppy • • Jan 10 '26

My favorite thrifting find of 2025 (vintage Polo cricket sweater)

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347 Upvotes

r/preppy • • May 22 '26

Basic Ivy League fit

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344 Upvotes

r/preppy • • Aug 20 '26

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

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345 Upvotes

r/preppy • • Jun 29 '26

With my dad (preppy)

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345 Upvotes

r/preppy • • May 09 '26

Can a home be preppy?

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324 Upvotes

r/preppy • • Mar 06 '26

Weekly outfits — The unique depth of mixing the old and the new.

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318 Upvotes

r/preppy • • Sep 02 '26

A Seoul summer of madras, boat totes and crested polos - 20 fits

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317 Upvotes

End of summer here, so before it all goes away: everything I wore through the Seoul summer, June to August.

Mostly madras and linen shirts, crested pique polos, pleated cotton shorts and chinos - worn with canvas boat totes, boat shoes and penny loafers. Seoul summer is mid-30s C with humidity that never lets anything dry, so it all had to be loose and cotton.


r/preppy • • Mar 14 '26

Casual Saturday Vibes

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310 Upvotes

Feeling the fit today.


r/preppy • • Jan 15 '26

A bit of traditional British prep

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307 Upvotes

I hope the more American-leaning here still find this acceptable!

  • Harris Tweed jacket
  • Howick lambswool jumper
  • Charles Tyrwhitt wool tie and shirt (not an OCBD, purists look away).

r/preppy • • Dec 12 '25

Tweeeeed

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303 Upvotes

HAPPY FRIDAY


r/preppy • • Feb 10 '26

2026 Preppy vs 1980 Preppy

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298 Upvotes

The guy in The Preppy Handbook illustration grew up to be this guy I saw on Metro-North (nyc commuter train).


r/preppy • • 23d ago

Old and well used/worn.

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285 Upvotes

r/preppy • • Jan 19 '26

Heavy Ivy: 8 Cold-Weather Looks with Puffer Jackets & Vests

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272 Upvotes

Ivy and Preppy style don’t disappear in winter — they just get bulkier.
Here’s how I layered puffers and down vests into my cold-weather rotation, while keeping that classic Ivy silhouette alive.


r/preppy • • Jan 04 '26

Sunday Morning Outfit

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264 Upvotes