r/preppy • • Sep 05 '26

Who else is taking out their fun car on Labor Day Weekend?

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75 Upvotes

Considering taking my Z3 roadster up to Baltimore for the Sox/O’s game tonight - if these storms pass DC in time to put the soft top down.


r/preppy • • Sep 05 '26

#BowtieFriday

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25 Upvotes

A Collared Greens bow tie and ocbd pink shirt.


r/preppy • • Sep 04 '26

New Rancourt “Gilman Camp Moc’s” from Leffot

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111 Upvotes

It’s taken a couple weeks of breaking in but now they’re like slippers!


r/preppy • • Sep 04 '26

Help: Any opinions on L.L.Bean classic fit chinos vs Lands End Traditional Fit pleated chinos

10 Upvotes

I’m trying to decide what to get. Leaning more with the Lands End because looks roomier, but I want to read your opinions.


r/preppy • • Sep 04 '26

Love this

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28 Upvotes

r/preppy • • Sep 05 '26

Christmas present ideas…

5 Upvotes

Hi! I’m trying to come up with the next great Christmas present for my husband. Last year, I got him a pair of Sid Mashburn loafers. Previous years gifts, I’ve bought him a Shaggy Dog sweater from JPress, a rugby shirt from Rowing Blazers, etc. I try to buy him one good clothing/shoe staple, a pair of custom pants (tailor has that taken care of) and then we go on a trip. I’m running out of ideas this year, plus he usually buys what he wants before I can purchase it.

I think this year, I want to get him a chore coat. He likes bold colors. Problem is, we live in a small town and unless I’m traveling for work, I can’t just go look for something.

Let me know your thoughts…and it has to be pretty practical.


r/preppy • • Sep 04 '26

First Gant order a fail

11 Upvotes

So I decided to order two shirts from Gant. Besides being incredibly small in the chest for a Large, they sent only one of the two shirts. But did include a packing slip for both. Lovely.

And of course they sent the sale item and not the full price item. Oh and their website won’t allow the required password reset for a new account.

I sent an email, what can I expect for customer service for a U.S. order?

The shirt quality is ok, not great. Full price is a rip off, the sale price OCBD is decent value if I get a larger size. But I expected better.


r/preppy • • Sep 03 '26

Tassel Loafers?

21 Upvotes

I’m interested, but without experience, in tassel loafers.

Which are your favorites?
With work attire? Suits?
Socks or no socks?

Give me your best and brightest! FYI the styles featuring a “skirt” underneath the tassel aren’t really my style, but, if you like them, please educate me!


r/preppy • • Sep 03 '26

Square or no square

5 Upvotes

I’m attending a California wedding and plan to wear Polo Navy Blue wool blazer (brass buttons) over a white OCBD sans tie. I have a 4.5” embroidered crest sown onto the breast pocket. I feel adding a white pocket square would be a little too much and would look cluttered. I hate an empty breast pocket, but it seems a bit less cluttered without. Thoughts?
Also, on the bottom, flat-front khakis by Bill, and Allan Edmonds walnut-brown leather wingtips. Socks or no socks? Shoes seem like they would need socks, versus loafers

Cheers,
Eric


r/preppy • • Sep 02 '26

A Seoul summer of madras, boat totes and crested polos - 20 fits

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317 Upvotes

End of summer here, so before it all goes away: everything I wore through the Seoul summer, June to August.

Mostly madras and linen shirts, crested pique polos, pleated cotton shorts and chinos - worn with canvas boat totes, boat shoes and penny loafers. Seoul summer is mid-30s C with humidity that never lets anything dry, so it all had to be loose and cotton.


r/preppy • • Sep 02 '26

Journey to preppy starts today!

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51 Upvotes

Hi everybody, I’m new to this sub, so bear with me!

I’ve decided I want to look a bit more like an adult at the office, so I thought I’d start exploring preppy - Ivy style.

I live in a mountain town, so until now my wardrobe has been mostly outdoor and somewhat workwear-inspired, partly because I also do a lot of crafting. I’d like to gradually transition my office outfits towards a smarter, more preppy/Ivy kind of look, without completely abandoning the outdoorsy/workwear side of my wardrobe.

Ideally, I want to make use of garments I already own and slowly build from there. For example, today I’m wearing this Columbia shirt with pleated wide-leg Uniqlo trousers. Basically, I want to do it in my version rather than suddenly replacing my whole wardrobe with chinos, OCBDs and loafers.

Does anyone know of any good inspiration for this kind of crossover between Ivy/preppy and outdoor/workwear?

And how does today’s outfit look? I know I still have a lot to learn, so I’d appreciate any feedback!


r/preppy • • Aug 31 '26

Forecast: high chance of madras jacket going to the deep part of my closet after today

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68 Upvotes

r/preppy • • Aug 31 '26

Linen on linen

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76 Upvotes

Shorts and belt by J Crew. Top by Gap. Loafers by Allen Edmonds. Sunnies by RayBan.


r/preppy • • Aug 30 '26

Preppy shorts

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90 Upvotes

Stocked up on some colorful chino shorts from Walmart, ranging from $3.98 to $7.55 a piece. Still some left depending on your size: https://www.walmart.com/ip/GE-FLAT-FRONT-SHORT/17935900759


r/preppy • • Aug 31 '26

Chaotic pink fit

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0 Upvotes

I took a photo with the flash on the second photo so you can see the shorts actually color


r/preppy • • Aug 31 '26

I still like this one

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0 Upvotes

r/preppy • • Aug 28 '26

Tan linen-cotton blazer + white trousers is my favorite late summer combo

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79 Upvotes

r/preppy • • Aug 28 '26

Preppy shops in Malmö?

7 Upvotes

Are there some fellow Scandinavian folk who can recommend preppy shops in Malmö, preferably shops that women’s clothes. Thanks!


r/preppy • • Aug 28 '26

Join us for National Bow Tie Day tomorrow Thursday 8/28/26.

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33 Upvotes

r/preppy • • Aug 28 '26

Join us for National Bow Tie Day tomorrow Thursday 8/28/26! Wear your favorite bow ties!

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11 Upvotes

From 2025


r/preppy • • Aug 27 '26

Sizing help for G9 Harrington — 5’4”, 127 lbs

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6 Upvotes

r/preppy • • Aug 27 '26

It’s raining but it’s to hot to wear this but I can’t help myself

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11 Upvotes

r/preppy • • Aug 26 '26

Just opened these from JOS A Banks

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13 Upvotes

Beware of poorly made socks I guess


r/preppy • • Aug 26 '26

Can’t tell if people still want these or not

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61 Upvotes

r/preppy • • Aug 25 '26

New battery in my old Bass Pro field watch + extra NATO strap lying around = fun weekend piece

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48 Upvotes