| 90% of people here asking “Is this old money???” | 332 | TryHelping | | | | |
| Madras Season | 67 | mirdochegalwa | | | | |
| Columbia University poster, 1902 | 55 | Skeleturtle | | | | |
| Carmina Horsebit Loafers: High Quality, Low Price, works with all kinds of styles | 52 | Lord_Halvy44 | | | | |
| Every house needs a library | 51 | lovelesschristine | | | | |
| Bill Clinton shakes hands with John F. Kennedy, 1963. | 49 | Arkhamman367 | | | | |
| Ehi, my dawgs, rate my fit | 44 | Longjumping-Agent-51 | | | | |
| What Does Preppy Style Mean Now? | with Lisa Birnbach | 24 | sakura_drop | | | | |
| How to find old school preppy content? | 22 | RoboticAmerican | | | | |
| Recommendations for Summer Rain Jacket | 3 | MammothSurvey | | | | |
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