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Madewell Colorblock Vista Button Front Shift Shirtdress XS
$35
XS
Peter Millar Mens Crown Soft Cotton Silk Blend 1/4 Zip Sweater Black Size XL
$59
$168
XL
J Crew Sweater Mens L Burnt Orange Lambswool Blend Crewneck Pullover Preppy
$25
L
Peter Millar Plaid Button Down Shirt Size Large Preppy Ivy League Country Club
$15
L
J. Crew Shirt Mens M Blue Gray Secret Wash Slim Fit Plaid Button Down Preppy Ivy
$27
M
Vtg 90's Ralph Lauren Mens Yarmouth 100% Cotton Oxford Shirt 15-33 Blue Preppy
$25
Neck 15
Weatherproof Vintage Green Plaid Mens XL Shirt Washable Linen Preppy Gorpcore
$18
XL
Brooks Brothers Blue Bermuda Shorts Cotton Preppy Chino Sz 35 Preppy Ivy League
$24
Waist 35
Lands End Traditional Fit Navy Red Plaid Shorts Size 38 Preppy Ivy League Golf
$15
Waist 38
Ralph Lauren Navy Striped Button Down Shirt Classic Fit SZ L Prep Ivy League
$20
16 1/2 34/35
Brooks Brothers Makers Men's Silk Tie Blue Gold Repp Stripe Preppy Academia
$27
OS
American Eagle Outfitters Dark Brown Crewneck Sweater Size S/P
$10
S
Ralph Lauren Men's Multicolor Plaid Button Down Shirt SZ XL Preppy Ivy League
$21
XL
Harvard University Cropped Hoodie Women's Burgundy Sweatshirt Women's XS/S
$13
S
Harvard Cropped Sweatshirt Gray Crewneck Ivy League Graphic Size S
$30
$59
S
Princeton University Hoodie Under Armour Women All Day Hoody Black Fleece Small
$20
S
Vintage Harvard Shirt Mens XL Gray Spell Out Ivy League College
$25
XL
Polo Ralph Lauren Navy Braided Stretch Belt Brown Leather Old Money Preppy EUC
$45
$999
OS
Polo Ralph Lauren Blue & Navy Striped 1/4 Zip Sweater Size L (14–16)
$38
L
VTG Womens Plaid Blazer Sz M English Countryside Preppy Ivy League Heritage
$23
M
Brooks Brothers Regent Fit XXL Blue Stripe Watermelon Embroidered Button Down
$33
XXL
Vintage Princeton Tigers Crest Graphic Tee Brown Medium 90s Ivy League College
$20
M
Polo Ralph Lauren Long Sleeve Polo Shirt Flesh Pony Classic Fit Navy Blue Mens L
$27
$222
L
Ralph Lauren Shirt Mens M Green Red Blaire Tartan Plaid Button Down Preppy Ivy
$35
M
Vintage Sears Roebuck Gray Knit Varsity Cardigan Sweater Size L
$40
L
Ralph Lauren Navy and Green Plaid Shirt Classic Refined Preppy Ivy League SZ XXL
$21
XXL
Ralph Lauren Mint Green Casual Button-Down Shirt Preppy Y2K Ivy-League Size M
$17
M
Polo Ralph Lauren Baby Rugby Shirt 12M Navy Yellow Stripe Crest Logo Preppy
$18
$79
9-12M
Moschino Blazer Cheap and Chic Navy Gold Button Wool Preppy Academia Size 12
$162
US 12
Pendleton Wool Midi Skirt Size 8 Pockets USA Minimalist Careerchic Deadstock New
$42
$94
US 8
Yale University T Shirt Retro Bulldog Blue Short Sleeve Tie Dye Womens Size M
$19
M
Polo Ralph Lauren Mens Medium Brown 1/4 Zip Pullover Sweater Estate Rib Knit
$30
M
Banana Republic Merino Wool V Neck Quiet Luxury Minimalist Office Pullover Small
$35
S
Brooks Brothers Cardigan Argyle Merino Wool Preppy Ivy League Preppy Mens Large
$50
L
Harvard University Cambridge Bookstore Woman's XL Maroon Tshirt NWOT Ivy
$17
XL
Polo Ralph Lauren Pink Pima Cotton Chino Shorts Classic Fit Preppy 32 Ivy League
$25
Waist 32
Lauren Ralph Lauren Sport Coat Blazer Men's 46 L Brown Preppy Jacket
$39
46L
Ted Baker London 'Get Knotted' 100% Silk Orange/Navy Striped Made in the USA Tie
$30
$999
OS
Brooks Brothers Brooks English White Buck Oxford Shoe EU 40 Women's 9 England
$125
$599
US 9
Vintage 90s Yale University Champion Reverse Weave Crewneck Sweatshirt Large
$275
L
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