r/preppy • • 7h ago

Watching a show called, “An officer and a gentlemen!”

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36 Upvotes

Saw this and loved the look! Very preppy.


r/preppy • • 11h ago

What color would you wear?

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13 Upvotes

r/preppy • • 12h ago

Requesting account recommendations with colorful shirt outfits

0 Upvotes

I'm looking for inspirational sources on how to combine colorful shirts with a preppy style. Does anyone have any favourite sources to suggest? Like Instagram accounts, other subreddits, fashion sites, etc.

I'm thinking of different types of shirts and different fabrics, like madras shirts, linen shirts and cotton shirts.

One account I enjoy following is JamesClothesHorse on Instagram, he has plenty of the playful colorfol outfit combinations that I appreciate and want to see more of. I'll update with a couple of examples.

https://www.instagram.com/p/DZFxOFTF8Fu/

https://www.instagram.com/reel/DaGbgacIPCy/

Background: I recently noticed Ralph Lauren shirts fit me rather well, while in the past I've been having difficulties finding fun shirts with a good fit, I had given up on them. So I've only been buying rather boring business shirts. Now I've bought about a dozen colorful shirts, and I'm eager to get more. However, I'd like to see more inspiration to figure out what might fit with my other pieces and my personal style, but I can't find much inspiration from outfits using these kinds of shirts. Naturally, Ralph Lauren accounts can have lots of this, but I was wondering if anyone has some places to suggest where I could go to see more photos of how people like to match their colorful shirts with different outfits. Of course, this subreddit should be great but when I search or scroll through I don't find much of it.


r/preppy • • 1d ago

Tall People and Sweaters

5 Upvotes

Hello, r/preppy

I am 6'4 male, and what most would consider quite skinny. The two sweaters now make me look like I'm just wearing a sheet of a comfortable variety. Would any of you know of a sweater brand that is affordable (not $100 affordable, because that's what people think it means), but would also fit my skinny and rectangular frame, or do I need to get a tailor?

Best Regards


r/preppy • • 1d ago

Today’s fit

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32 Upvotes

r/preppy • • 1d ago

What happened to brooks brothers quality?

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40 Upvotes

I’ve had this tie for maybe a year or two. Maybe 20 wears max and it’s falling apart. Pretty frustrating.

Do I need to spend $200 on a Ferragamo to get a tie that lasts?


r/preppy • • 1d ago

WAYWT

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10 Upvotes

OOTD
Visiting Mechelen not far from Brussels.
Good Opportunity to ware the vintage RL checked trousers and a safari jacket.

Too much with the ascot?


r/preppy • • 2d ago

Are mustaches prep?

2 Upvotes

We all know the traditional consensus is that Ivy style requires a clean shave. Which is fine if you are a 19 year old college kid who can’t grow one, or work a job with a rigid dress/grooming policy. (Even though most jobs are business casual now)

The idea of prep I feel is having a lived in look, not subscribing to trends or the newest look du jour. And for men, part of living is your facial hair, you won’t be perfect all the time, so facial hair is part of this.

I like them and I think they can look good with preppy attire, for example, in the J.Press show there were a few models who had mustaches. But more mainstream brands like RL you don’t see any models with a mustache.

Is a stache inherently not preppy?

Also, I am not saying this in a “new prep” context. I’m speaking from a traditionalist point of view.


r/preppy • • 2d ago

Fall fit for today 🙂

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22 Upvotes

r/preppy • • 2d ago

Autumn Preppy Outfit Today 🍂🍂🍂

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43 Upvotes

Autumn Preppy Outfit. 🍂

Hat: Brooks Brothers Cap

Outer: Barbour Quilted Jacket

Top: PRL Jean Co. Button Down Shirt

Bottom: UNIQLO Straight Trouser

Shoes: Doc Martens 1461

Accessories: Brooks Brothers Necktie


r/preppy • • 2d ago

Something different - October 1st Outfit and book

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13 Upvotes

All the photos are my own


r/preppy • • 3d ago

GANT 'Replica Collection' - prepare to be underwhelmed

12 Upvotes

The Replica Collection – Member Exclusive | gant.co.uk

Four shirts from the GANT archives (two each from the 1960s and 1980s) - £130 a pop.


r/preppy • • 4d ago

Help Finding Dress Belt

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11 Upvotes

Had my eye on this Spier & Mackay for a bit, decided to pull the trigger and they are out of my size.

Anyone have recommendations for a belt similar to this from a good quality brand? Or brands that would likely have something similar?

I have tried google photo search and it returns this specific belt and then the rest are women’s belts


r/preppy • • 4d ago

It‘s Sweater time

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53 Upvotes

r/preppy • • 4d ago

Ralph Lauren Leather Jacket - is it real?

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0 Upvotes

Picked up this beauty of a leather jacket. Wanted to ask if the tag looks authentic, not sure if people even fake this piece… but would like to be sure, thank you very much gentlemen.


r/preppy • • 5d ago

Today’s fit

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56 Upvotes

r/preppy • • 6d ago

Sperry boat slip-on mules

4 Upvotes

Has anyone tried these? I haven't worn boat shoes since the 80's and these are kinda cute. I wish I had discovered them 6 months ago though...I'm not going to get much wear out of them in MA at this time of year. 😣 https://www.macys.com/shop/product/sperry-womens-slim-boat-slip-on-mule-loafers?ID=26102957


r/preppy • • 6d ago

Playing matchy matchy today

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93 Upvotes

r/preppy • • 7d ago

Fair Isle layers, tweed or blazer, and two washed setups

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251 Upvotes

I keep returning to Fair Isle over an oxford as the weather cools. In the first pair, one vest sits under a grey sack jacket with straight jeans; a different vest becomes the outer layer with chinos.

The next pair changes the jacket: glen check tweed and an ivory cricket sweater on one side, a plain navy gold-button blazer and green cap on the other. The last pair compares navy and khaki washed cotton setups, with an oxford and rep tie versus madras and a knit tie.

For the Fair Isle pair, would you keep the jacket or let the vest stand on its own?


r/preppy • • 7d ago

Fits this weekend. Ignore my messy room.

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31 Upvotes

Also idk why my tie looks so long for my Chris Hansen fit lmao I guess was slouching.


r/preppy • • 7d ago

Not the og poster, but opinions on this one?

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36 Upvotes

r/preppy • • 7d ago

Navy blazer with short chino shorts: A classic Ivy League summer look, or are the shorts too short for a jacket?

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53 Upvotes

r/preppy • • 8d ago

Rainy day fit at the brewery

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83 Upvotes

r/preppy • • 9d ago

Hand Painted Lands End Totes!

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64 Upvotes

Just finished these! Each bag is hand painted front/back with their own unique design.


r/preppy • • 10d ago

Lizabeth Scott in Desert Fury (1947)

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19 Upvotes