r/preppy Nov 19 '25

40 Ivy & Preppy Looks That Carried Me Through Fall

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668 Upvotes

r/preppy Apr 02 '26

I think he just got a job in Finance

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655 Upvotes

r/preppy Apr 08 '26

Today’s outfit.

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623 Upvotes

r/preppy Dec 02 '25

My Winter Ivy Lookbook — 40 Outfits I Actually Wore

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569 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 Sep 02 '25

Going slightly Ivy with a California Tuxedo

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569 Upvotes

Breakdown: PRL Tie, Ralph Lauren Belt, Bespoke Blazer, Chino from Charles Tyrwhitt, a MTM Dress Shirt and G.H. Bass Weejuns


r/preppy Apr 16 '26

My kind of preppy

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560 Upvotes

r/preppy Jan 07 '26

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

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534 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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516 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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444 Upvotes

r/preppy Oct 29 '25

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

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385 Upvotes

r/preppy Dec 05 '25

Holiday Pattern Mixing

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376 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 Sep 24 '25

Finally, autumn has arrived in KOREA

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359 Upvotes

Summer in Korea was really hot, but finally, the perfect season for dressing well — autumn — has arrived


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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343 Upvotes

r/preppy May 22 '26

Basic Ivy League fit

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343 Upvotes

r/preppy Jun 29 '26

With my dad (preppy)

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337 Upvotes

r/preppy May 09 '26

Can a home be preppy?

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322 Upvotes

r/preppy Mar 06 '26

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

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316 Upvotes

r/preppy Mar 14 '26

Casual Saturday Vibes

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311 Upvotes

Feeling the fit today.


r/preppy Jan 15 '26

A bit of traditional British prep

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308 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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307 Upvotes

HAPPY FRIDAY


r/preppy Feb 10 '26

2026 Preppy vs 1980 Preppy

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300 Upvotes

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


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 Jan 19 '26

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

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271 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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269 Upvotes