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$29.99
VTG Dockers Pants Mens 33x30 Pleated Chino Old Money Succession Ivy Prep 90s
$29.99
VTG Pants Mens 31x33 Pleated Chino Old Money Succession Ivy Prep 90s Baggy
$39.99
Polo Ralph Lauren Pants Mens 32x32 Wool Trousers Old Money Baggy Pleat College
$45.00
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$30.00
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Merino Wool Men's 2X 52 Chest Big & Tall V Neck Pullover Academia Old Money Navy
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Vintage Sweater Mens Large Pullover Car Embroidery 90s USA Old Money V-Neck Golf
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$34.99
The Territory Ahead Pants Mens 34x34 Gray Back East Wool Herringbone Old Money
$33.88
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$24.99
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$150.00
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$38.00
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$31.90
J Crew Dress Pants Mens 33x29 Red Slim Fit Wool Classic Workwear Old Money
$35.99
Michael Gerald Sweater Men L Black Cardigan Button Grandpa Old Money Vtg 90s Y2K
$24.44
Yves Saint Laurent Shirt Mens 16 1/2 Button Up Dress Long Sleeve Old Money Y2K
$12.99
Cremieux Premium Shirt. Old Paisley Money - Size Large
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Tommy Hilfiger Men's 38 X 30 Tartan Trousers Wool Old Money Ivy League Pants
$29.95
Ralph Lauren Pants Mens 40X32 Flat Front Herringbone Trousers Tailor Fit Preppy
$37.82
TAYLOR STITCH Men’s The Merino Henley in Heather Black Long Sleeve sz 42 LARGE
$25.00
Vtg 90s Nautica Men's XL Black Long-Sleeve Button Down Shirt Red Logo Pocket USA
$22.95
Gap Button Up Shawl Cardigan Sweater Mens Small Preppy Casual Old Money Normcore
$42.99
Incotex Super 120s 100% Wool Gray Dress Pants Pleated Front Italy Luxury 34 x 30
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$45.00
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$50.00
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$50.00
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Turnball Asser Pants Men 40X32 Navy Blue Wool England Cuffed Old Money Preppy
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Lauren Ralph Lauren Mens Wool Dress Pants Size 34X32 Gray Plaid Office Old Money
$33.95
Ralph Lauren 16.5 36/37 long sleeve button shirt classic fit stretch houndstooth
$19.88
Christian Dior Button Up Shirt Men's L White Made in USA Luxury Old Money Classy
$14.39
Banana Republic Sweater Mens L Gray Italian Merino Wool Baruffa 1/2 Zip Office
$38.24
Eton of Sweden Shirt Mens 51 20 Blue Classiccore Old Money Preppy Business Dress
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Haggar Pants Mens 36x30 Freedom Dress Pant Pleated NWT Old Money Business
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VTG Pants Mens 36x30 Wide Wale Corduroy Pleated Old Money Succession Prep 90s
$19.99
Ralph Lauren Knit Button Up Shirt Mens 16 Flesh Pony Collared Jamaica
$55.00
Armani Collezioni Mens 36 (measures 34x30) Dress Pants Cuffed Pleated Stripes
$32.00
NEW Old Navy Ultimate Tech Athletic Green Pants Tag 33x30 measured Size 33x30
$31.77
J McLaughlin Blue Old Money Preppy Cotton Yachty Dress Shirt Mens Medium
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$18.99
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$16.00
Hugo Boss Shirt XXL Premium ButtonUp Old Money Preppy Softboy Grandadcore#20536
$35.99
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$40.00
Vintage pleated dress pants black wool blend watch pocket 33x30 old money style
$19.99
Theory Shirt Mens XL Button Up Gingham Check Preppy Old Money Quiet Luxury
$27.88
Tchibo German Wool Cozy Grandpa Grunge Dark Academia Preppy Old Money Sweater M
$24.95
Robert Graham Shirt Mens Large Blue Striped Old Money Wall Street Casual Office
$70.00
EMPORIO ARMANI Gray Wool Old Money Mock Jumper US Size 36 Large Made in Italy
$19.99
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$15.99 to $19.99
Old School T Shirt Lucky 13 Retro Vintage Poker Card Casino Clothing Classic Tee
$169.00
Polo Ralph Lauren Olive Heather Cashmere Cable Knit Sweater Old Money Luxury
$21.50
Land's End Traditional Fit Sailcloth Chino Pants Kelly Green Old Money Preppy 34
$18.74
Bonobos Chino Pants Mens 34 Green Khaki Old Money Career Preppy Dark Academia
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