▲ 0 r/preppy

There’s a lot of toxic perfectionism in being Preppy and this subreddit

I am also a big contributor of that problem sorry guys

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u/ThisSeries2814 — 1 day ago
▲ 0 r/preppy

I’m sorry for having ADHD but are The Hardy Boys and Nancy Drew considered Preppy?

u/ThisSeries2814 — 2 days ago
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Define Preppy?

My working definition of Preppy is Wealthy family’s who attended private school in America and plays expensive sports like Polo Rowing, Sailing Tennis, Cricket

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u/ThisSeries2814 — 2 days ago
▲ 0 r/preppy

My fit to go gawk at Preppy clothes at a mall that I live 50 minutes from and then to see my clients after

u/ThisSeries2814 — 2 days ago
▲ 25 r/preppy

My growing sweater collection

I am also very proud of this!, last photo is my dad’s Temple sweater that I inherited when he died, (miss him so much!)

u/ThisSeries2814 — 2 days ago
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Da fit

Just bought my first pair of topsiders super excited to wear these!, also this post is for you @u/ngolds02

u/ThisSeries2814 — 5 days ago
▲ 16 r/Watches

[Rottweiler watch] bought my first watch

I bought my first watch for $45! (Kinda crazy) I am focused on being in the preppy aesthetic so this watch is supposed to give Preppy vibes I want to buy other more known watches that give off that vibe any suggestions would be appreciated ;), This watch is from Chipp Neckwear which is associated with the Iconic Chipp Tailoring from the 1980s, one of the straps broke on the watch immediately which isn’t surprising since it was only 45

u/ThisSeries2814 — 6 days ago
▲ 0 r/preppy

Does this work together?

Just got my first watch from Paul Winston/Chipp Neckwear which is apparently apart of the iconic Tailor Chipp Tailor from 1980s and the only reason I know this is from Matthew Longcore, anyway just bought this cool vintage belt from EBay and absolutely adore it

u/ThisSeries2814 — 6 days ago
▲ 17 r/preppy

Fun Preppy haul

Tommy Bahama Nantucket reds, Tommy Bahama socks, Ll Bean Polo, Brooks Bros Sweater, Brooks Bros long sleeve shirt, Brooks Bros Sweater, Sambas

u/ThisSeries2814 — 9 days ago