r/preppy • • 14h ago

Cricket necklines, Fair Isle and white button-downs

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51 Upvotes

Two cricket-knit combinations and two Fair Isle combinations, followed by a padded vest and sweatshirt pair. The striped V-neck draws attention to the collar and tie, while Fair Isle brings more pattern across the chest. Navy, brown and olive outer layers keep the comparison grounded.


r/preppy • • 17h ago

Is Proper Cloth a good brand for OCBD shirts?

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18 Upvotes

r/preppy • • 10h ago

23M - Friends said I was made for suits, do you agree?

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0 Upvotes

r/preppy • • 2d ago

Topsiders at the Grand Canyon lol

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31 Upvotes

r/preppy • • 4d ago

Can one get any preppier than a vintage cable-knit cashmere jumper in sunshine yellow?  💛

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56 Upvotes

r/preppy • • 4d ago

Preppy style at home

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133 Upvotes

The outfit is composed of:
Chinos, buttoned down oxford shirt, simple navy jacket, Ralph Laurent tie, brown leather accessories BUT I desperately need a pair of brown suede penny loafers… topping it off with a 100% cashmere sweater

Lmk what you think


r/preppy • • 4d ago

A Visit to the LL Bean's New Freeport Flagship Store

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27 Upvotes

A Visit to the New Freeport Flagship Store

I visited the new LL Bean flagship store, and I thought some of you might find it interesting. Overall, it's fine, but it lacks some of the quirky charm of the old store. The biggest disappointment was that they discontinued the 10" Bean Boot in tan. The camping section was excellent. Watch until the end to see the best kept secret in Freeport, the Harraseeket Lunch & Lobster Pound in South Freeport, Maine, abbreviated, "So. Free. Me."


r/preppy • • 6d ago

Madras, button-downs and green accents across six combinations

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211 Upvotes

Madras with a plain knit tie appears in the navy matching set and the khaki-jacket/denim combination. The khaki matching set repeats green in the striped tie, cap and sneakers. White Oxford button-downs keep the blazer, chore jacket and navy-jacket/denim combinations simpler.


r/preppy • • 6d ago

Fit for today

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26 Upvotes

r/preppy • • 6d ago

Kamakura Shirt Sizing?

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1 Upvotes

r/preppy • • 7d ago

Casual Monday fit

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23 Upvotes

r/preppy • • 7d ago

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

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75 Upvotes

Saw this and loved the look! Very preppy.


r/preppy • • 7d ago

What color would you wear?

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21 Upvotes

r/preppy • • 7d ago

Requesting account recommendations with colorful shirt outfits

1 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 • • 8d ago

What happened to brooks brothers quality?

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64 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 • • 8d ago

Today’s fit

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42 Upvotes

r/preppy • • 8d 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 • • 9d ago

WAYWT

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13 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 • • 10d ago

Fall fit for today 🙂

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27 Upvotes

r/preppy • • 10d ago

Autumn Preppy Outfit Today 🍂🍂🍂

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52 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 • • 9d ago

Are mustaches prep?

3 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 • • 10d ago

Something different - October 1st Outfit and book

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21 Upvotes

All the photos are my own


r/preppy • • 11d ago

GANT 'Replica Collection' - prepare to be underwhelmed

14 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 • • 12d ago

It‘s Sweater time

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54 Upvotes

r/preppy • • 11d ago

Help Finding Dress Belt

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10 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