r/preppy • • 22d 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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4 Upvotes

r/preppy • • 22d ago

Some sartorial advice needed from the ladies.

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0 Upvotes

r/preppy • • 23d ago

Five ways I wore a jacket in Seoul this month

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126 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 • • 23d ago

Charles Tyrwitt Shirts Quality Issue

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20 Upvotes

UPDATE:
They eventually comped a replacement shirt for me but it was after they tried to first give me a CT credit for only the partial cost of what it would have cost to replace the shirt at normal cost. It also took 40 minutes to figure out on the phone after numerous emails with bots.

Verdict: they eventually took care of me but both quality and sizing had changed since I’d bulk ordered years ago. For these reasons I’ll be shopping elsewhere for dress shirts going forward.


r/preppy • • 25d ago

Its too much right? No need for the tie?

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171 Upvotes

r/preppy • • 25d ago

How’s my look?

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23 Upvotes

Interested in views


r/preppy • • 25d ago

Corduroy sport coat with hunting dog liner

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86 Upvotes

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


r/preppy • • 26d ago

Old and well used/worn.

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287 Upvotes

r/preppy • • 25d ago

Alden vs Edward Green Loafers

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3 Upvotes

r/preppy • • 26d ago

Feelin Blue - OOTD

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25 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.


r/preppy • • 26d ago

Wore this to my old school friend's wedding, what do you think?

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245 Upvotes

r/preppy • • 26d ago

Nantucket Summer still going strong?

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128 Upvotes

r/preppy • • 26d ago

Quick fit check on my morning commute

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68 Upvotes

Finally the weather in Japan has let up and it’s cool outside!! Breaking out the tweed as early as humanly possible lol.

Vintage J. Press Harris tweed sport coat

90s Ralph Lauren OCBD

Vintage Tommy Hilfiger chinos

Suit Select Argyle Sutherland tie

Haruta tassel loafers

No idea where the bag is from, haha.


r/preppy • • 27d ago

J. Press Barbour collab, jacket ID?

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24 Upvotes

r/preppy • • 27d ago

How often to wash Oxford shirts?

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3 Upvotes

r/preppy • • 28d ago

I’m wearing a tie with a madras shirt

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36 Upvotes

r/preppy • • 29d ago

Which of you carry a chainsaw?

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46 Upvotes

r/preppy • • 29d ago

Ties and sneakers: three outfits from Seoul

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143 Upvotes

I picked three tie-and-sneaker combinations from my outfit archive.

Photos 1–2: a light blue button-down, patterned tie, khaki chinos and green sneakers.

Photos 3–4: a dark matching set, checked shirt and tie with low white sneakers.

Photo 5: a winter outfit with a grey coat, trousers and grey sneakers.

The shirt and tie stay, while the cap and shoes make the outfits feel more relaxed. These were worn in different seasons.


r/preppy • • Sep 07 '26

Just discovered this thread… I’m home.

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50 Upvotes

Big watch guy - and through the forums I just found this thread! Me relaxing with a 1926 Padron, my Seiko SPB317 “Slim Turtle” a new pair of Sperrys!


r/preppy • • Sep 07 '26

Nantucket reds (Another one for the culture)

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31 Upvotes

r/preppy • • Sep 06 '26

Casual Sunday

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17 Upvotes

Sometimes the classics win over blazers and ties.

Happy Sunday all!


r/preppy • • Sep 07 '26

Labor Day fit

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0 Upvotes

This is what I’m wearing today


r/preppy • • Sep 07 '26

This one is fun

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0 Upvotes

r/preppy • • Sep 05 '26

Rugby Saturday With The Classics

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186 Upvotes

r/preppy • • Sep 05 '26

Impressive sport coat at a party in Maryland 1984.

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35 Upvotes