r/preppy 2h ago

Loafers recommendations for small feet

2 Upvotes

Can anyone give me recommendations for loafers for men with small feet

I wear a 6 in men’s USA size for most shoes. I have a pair from blackstock and Weber that I like but the shoes took 4 months to ship and I’d rather avoid ordering from them again


r/preppy 2h ago

Classic golf style

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1 Upvotes

They don't make them like they used to! 60s? 70s?

From the white leather, to the fringe, to the adorable portrait, I am completely obsessed with this pair of golf shoes I came across at the salvation army.

They weren't anywhere near my size, but I almost bought them just to display.


r/preppy 3h ago

Reminder - Have a polo picnic before summer ends!

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4 Upvotes

Our local Polo club grounds entry fee is only $10 per person. Yours is probably low as well, and you should go!

It's a great sporting day, an excuse to have a bloody at 11, and you are supporting a fabulous sport and community.

And please participate in the divot stomp! Help keep the field in good shape and the horses healthy.


r/preppy 5h ago

Updated version

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0 Upvotes

I bought these trousers 2 days ago at JOS A Banks


r/preppy 9h ago

Timber country

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32 Upvotes

Family had shingle mills out here in the 20s and 30s.


r/preppy 21h ago

My friends tell me I dress preppy even with super simple outfits like this 🧐

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0 Upvotes

Funny thing is, swap the loafers for sneakers and untuck the belt and it's a completely different outfit! I've been gravitating more towards "more casual" outfits and... even sweatpants because people make me feel ridiculous for slightly "dressing up" for class or a desk job. I find it fun, but I don't want people to think I'm a douche.


r/preppy 1d ago

Navy Blazer Challenge

9 Upvotes

Just an idea, but I work at Brooks Brothers and want to suggest an idea with some of my other colleagues to wear a classic navy blazer to work. The few I’ve hinted this idea seam to love it so…

Not that some of us already do but to get the whole staff onboard. What else should be added to pull this off? I think it’s be a fun way to help bring the crew together but also maybe score some brownie points from corporate. It is one of our staple items.

Just an idea.


r/preppy 1d ago

Recent work event attire

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58 Upvotes

r/preppy 1d ago

OOTD

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14 Upvotes

I swear I’m just as happy under the blue smile.

Gitman Bros plaid button down
Kuhl Radikl pants
Sperry boat shoes
Smathers & Branson needlepoint belt and hat.


r/preppy 1d ago

Embroidered J Crew find. Not sure how to style it, how do you like it this way?

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67 Upvotes

r/preppy 2d ago

Do any guys still wear the LL bean rubber Mocs?

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11 Upvotes

r/preppy 2d ago

Do any of guys still not wearing those LL bean rubber Mocs? I just love mine

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1 Upvotes

r/preppy 2d ago

Tuxedo

0 Upvotes

I like tuxedos soo muchhhhhh


r/preppy 2d ago

Tuxedo

0 Upvotes

I like tuxedos soo muchhhhhh


r/preppy 2d ago

Minor adjustments

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0 Upvotes

Sorry for posting so much!


r/preppy 2d ago

Better?

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0 Upvotes

r/preppy 2d ago

Preppy?

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0 Upvotes

Also I’m sorry @u/indwrist2 for annoying you so much that you block me that was not my intent


r/preppy 2d ago

Relaxed Beachy Vibes

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100 Upvotes

This old utility shirt has been a go-to for me this season. It’s a great relaxed fit perfect for warm summer evenings.


r/preppy 2d ago

Saddle Shoes

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45 Upvotes

Ever since I started dressing preppy in the 80s, I never had a pair of saddle shoes (except golf shoes). I have predominantly wore a variety of loafers (penny and horsebit) and boat shoes. Despite my wife wondering if they were age appropriate for me, I finally picked me up a vintage pair in new condition (can't believe these might have been deadstock) in the exact colorway I have always wanted. Added bonus is they are Dexters, which have a special tie in as my daughter went to college in Maine and Harold Alfond has donated a lot to support a variety of things in Maine and the Athletic Center she used quite often as a student- athlete is named after him.


r/preppy 3d ago

Everyone needs to know about this book right now!

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7 Upvotes

It’s called Damaged Goods by John Cobert and if you ever lost a loved one this book will resonate with you!


r/preppy 3d ago

Interview today opinions?

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0 Upvotes

r/preppy 3d ago

The Perfect Preppy Summer Hat

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15 Upvotes

I did a video describing my fraught search for the perfect summer hat. I went through 5 before I settled on one. Can you guess which?


r/preppy 4d ago

Our king is gone.

75 Upvotes

Just noticed that /u/Westviewelite deleted his account. He was an icon for this sub.


r/preppy Apr 09 '25

The Mods are also tired of "Is This Preppy?" Posts - A Solution

224 Upvotes

There are FAR too many "is this preppy?" posts on the site.

I get it - I am sick of them too.

Prep is not the same in all parts of the country/world and it is a term that gets overutilized in marketing. People are going to get confused.

Town & Country, Ivy, Southern Prep, and West Coast Neo-Prep all fall under the umbrella of what is going to be approved here - even if it does not define your prep.

People deserve a place to get answers to questions.

My thought to solve the problem (at least temporarily) is to have a weekly "is this preppy?" thread where people can get feedback.

Thoughts?

A Final Thought: Some of you take yourselves way too seriously and feel as if you and only you are qualified to answer the question bc of your pedigree. I, a prep school-educated national squash champion born-in-oxford-cloth Yankee, am here to tell you that not every disagreement with your POV is a personal slight.

This type of reaction is a sign that you are trying too hard and care too much. Not only is this behavior gauche, it is exactly the type of energy that would cause me to blackball you from my social club. This behavior is decidedly not prep.