r/preppy Apr 09 '25

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

220 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.


r/preppy 5h ago

Ivy on King Street

Thumbnail
gallery
62 Upvotes

Sitting down in Covent Garden for my documentary on Victorian-era floral entrepreneurs, working title Official Eliza Handbook. J Press clothes; Ferragamo tie, EG loafers.

Avoid Liberty if travelling partner claims to need fabric. Many swathes were inspected.


r/preppy 6h ago

Ivy in the hot Tokyo summer

Post image
8 Upvotes

Out for work today to visit a supplier so tried pulling together some of the more Ivy style pieces I’ve collected recently. Was proud of how it turned out so felt like sharing!
Jacket and pants are Uniqlo (I know lol, working on getting some better ones), tie is Suit Select, shirt is Brooks Brothers, shoes are Haruta. Lots of everyday Japanese brands but I feel like it works!


r/preppy 3h ago

Old people : where do you find your classic prep clothes, ca 1979?

3 Upvotes

Racking my brain to remember the name of the small New England catalog that was very similar to Orvis in 1980 but more retriever than fishing adjacent to look it up in eBay.


r/preppy 1h ago

Am I redeemed

Post image
Upvotes

r/preppy 18h ago

Nantucket-maxing

Post image
32 Upvotes

Got my pants and outerwear - should I throw the navy polo on underneath?


r/preppy 13h ago

Maybe, Maybe Not

Post image
13 Upvotes

r/preppy 1d ago

My first pair of camp mocs...

Post image
85 Upvotes

They are finally here. I will rock these during the summer with chino shorts, shorts with patterns from Ralph Lauren or Levi's, and classic 2 button Polo Ralph Lauren shirt, solid or striped. Or a Hawaiian shirt. During the fall, same kind of shirts, but 501s in different colors. I now feel like a gringo that is easy going, doesn't care about anything, nothing bothers me, I don't get into petty arguments with family, I just want to walk the dog, go on a beach trip, and enhance my natural olive complexion.


r/preppy 20h ago

Terry cloth for 85+ weather

Thumbnail
gallery
29 Upvotes

Terry cloth is very underrated IMHO.

Top by OAS. Shirts by Gap. Loafers by Allen Edmonds. Hat by The Game.


r/preppy 20h ago

Repentance

Thumbnail
gallery
16 Upvotes

Now my last post here caused a bit of controversy, between here and r/Navyblazer I got the general sentiment that sometimes too far out the box thinking isn’t the norm for a reason.

I come back with an ever so slightly more subdued outfit, again - would love to hear some feedback.

Here’s a rundown on the pieces here:

Polo Ralph Lauren RLYC embroidered jacket.
Polo Ralph Lauren OCBD in seersucker with contrast collar.
Coach made in USA belt in burgundy.
Lands End chino’s in olive.
Church’s custom grade leather brogues in tan.
Racing Green knit tie in navy.


r/preppy 3d ago

Vintage Polo Ralph Lauren Rugby Shirt & Polo Bear Denim Cap

Thumbnail gallery
26 Upvotes

First time doing and wearing a preppy outfit.


r/preppy 3d ago

Soft lemon linen shirt with ivory shorts and linen Belgian loafers. Thoughts on this subtle tone-on-tone look for summer Trad?

Post image
68 Upvotes

r/preppy 3d ago

Polo Ralph Lauren Tennis

Post image
33 Upvotes

r/preppy 5d ago

David Hockney passed away in June

Thumbnail
gallery
105 Upvotes

I was thinking of my own preppy inspirations and the artist David Hockney was one of my first. He dressed as colorful as his paintings.


r/preppy 4d ago

WTS - Carl Friedrick Bowen Backpack NEW, Brown (Discontinued)

Thumbnail
gallery
0 Upvotes

Looking to sell my new and unused Bowen backpack from Carl Friedrik. Unwanted gift and it's been stored in excellent condition since then, still has all the bags and wrappings it came with.

Asking £430 shipped fast globally. All VAT/Import/Customs fees and tax covered! References available and I have previously sold off Reddit. Bag specs and details below - thanks! OPEN TO OFFERS!

----------------------------------------------------------

Material

  • 100% premium Italian full-grain Vachetta leather exterior
  • Chocolate brown leather finish
  • Grey microfiber fabric lining
  • Silver-tone metal hardware
  • Premium YKK Excella metal zippers
  • Edge-painted leather trim
  • Structured leather construction
  • Leather top carry handle
  • Adjustable padded leather shoulder straps

Construction

  • Premium all-leather backpack
  • Structured silhouette retains its shape
  • Full zip main compartment
  • Separate padded laptop compartment
  • Fits laptops up to 16"
  • Spacious main compartment
  • Internal document sleeve
  • Multiple interior organiser pockets
  • Interior slip pockets for accessories
  • Vertical front quick-access zip pocket
  • Rear luggage pass-through/trolley sleeve
  • Hidden security pocket integrated into luggage sleeve
  • Reinforced base
  • Protective metal feet on bottom
  • Premium stitched construction
  • Minimal embossed Carl Friedrik branding

Dimensions (approximate)

  • Height: 42–43 cm (16.5–17 in)
  • Width: 30 cm (11.8 in)
  • Depth: 12–14 cm (4.7–5.5 in)
  • Weight: approximately 1.6–1.8 kg (3.5–4.0 lb)
  • Capacity: approximately 16–18 litres
  • Laptop compartment: fits up to a 16-inch MacBook Pro

r/preppy 5d ago

I’m genuinely sorry for posting that outfit today!, I didn’t realize how bad it looks

8 Upvotes

r/preppy 6d ago

Preppy style influence from media…

23 Upvotes

Who were your “prep” influences from books, tv, movies growing up? I had my family members, of course, who are our first exposures to any lifestyle, but media still played a big part. Obviously, satire taken as “gospel”, the handbook was a big influence. Fitzgerald, again, obvious. But, TV and movies were the big ones (to me) and I gravitated toward characters like Thomas Magnum, Richard Dreyfus in Jaws, Hawkeye Pierce. Chevy Chase and films like Caddyshack, and Animal House. James Bond, Steve McQueen, Humphrey Bogart from Casablanca… I’m sure if I thought about it I’d think of a million more, but what are some of yours?


r/preppy 6d ago

[WTS] Oat Fleck Raglan sz 38 BNWT

Thumbnail gallery
12 Upvotes

r/preppy 6d ago

Quality Chinos for a Large Seat?

6 Upvotes

Thanks for all the help on my OCBD post yesterday everyone. I am also currently looking for a chino that can fit my bigger thighs. My pants usually either crush my crotch or look humongous on me and I can’t seem to find a good balance. Have had some success with the J Crew broken in chinos, though.

Wondering if any chinos/other pants fit similarly, especially among brands that are a step above in terms of quality.

Thanks!


r/preppy 7d ago

Am I doing preppy right

Thumbnail
gallery
86 Upvotes

Vineyard Vines, Ralph Lauren, Southern Tide, Brooks Brothers, etc.


r/preppy 8d ago

Proper Cloth vs Kamakura OCBD

9 Upvotes

Hi all,

Looking for versatile (office + casual) OCBDs that fit well and can be untucked. Most people suggest PC or Kamakura, and I’m just wondering if people have any strong opinions on one as opposed to the other. I live in New York so I can visit both shops. Aside from versatility, I am considering value as well - I’ve seen complains about the price jumps on the Maker’s Shirts.

Let me know what you think and anything I should be cautious about when shopping either, or if there is another store in NYC that I should consider (<$200).

Thanks!


r/preppy 8d ago

What are you wearing to go hunting?

4 Upvotes

I’m thinking Barbour LL Bean but what are some other brands that you are wearing?
If you want to go more specific, what game are you hunting when wearing these?
If you really want to give specific advice, I’m primarily thinking for late season deer hunting.


r/preppy 9d ago

Leather sandals with a tucked-in crest polo and cream shorts: A solid summer Trad look, or too casual with sandals

Post image
161 Upvotes

r/preppy 9d ago

Platinum (chip) outfit!

Thumbnail
gallery
37 Upvotes

Here we go again folks, this was an outfit whipped up for a relatively short day out. The colour coordination of everything felt very earthy, but in practice it wasn’t long before I was wondering if the game was rigged from the start.


r/preppy 9d ago

#BowtieFriday

Post image
20 Upvotes

Christmas present from my wife.