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VTG New Expressions 15/16 Brown Plaid Lined 100% Wool Preppy Academia Made USA
VTG New Expressions 15/16 Brown Plaid Lined 100% Wool Preppy Academia Made USA

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VINTAGE Ralph Lauren Shirt Mens Size 15 Preppy Trendy Small Pony 100% Cotton
VINTAGE Ralph Lauren Shirt Mens Size 15 Preppy Trendy Small Pony 100% Cotton

$20.88

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Crewel Cross Stitch Wood Framed Pink Green Floral 21x15” Preppy Handmade Granny
Crewel Cross Stitch Wood Framed Pink Green Floral 21x15” Preppy Handmade Granny

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SuitSupply Button Shirt 15 White Preppy Outdoors Casual Formal Dress 38 Traveler
SuitSupply Button Shirt 15 White Preppy Outdoors Casual Formal Dress 38 Traveler

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80s Brooks Brothers Makers Oxford Shirt 15 White Made in USA OCBD Preppy Ivy
80s Brooks Brothers Makers Oxford Shirt 15 White Made in USA OCBD Preppy Ivy

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Polo Ralph Lauren Shirt Mens Small Blue Polo Rugby Slim Rowing Club 15 Preppy
Polo Ralph Lauren Shirt Mens Small Blue Polo Rugby Slim Rowing Club 15 Preppy

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VTG Brook Brothers Dress Shirt Mens 15-3 Blue Button Down USA Made Preppy READ
VTG Brook Brothers Dress Shirt Mens 15-3 Blue Button Down USA Made Preppy READ

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Ralph Lauren Shirt Mens 15 32/33 Blue Striped Yarmouth Oxford Pony Preppy VTG
Ralph Lauren Shirt Mens 15 32/33 Blue Striped Yarmouth Oxford Pony Preppy VTG

$16.99

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Brooks Brothers Shirt Men 15 Blue Stripe Regent Supima Cotton Preppy Dress Party
Brooks Brothers Shirt Men 15 Blue Stripe Regent Supima Cotton Preppy Dress Party

$27.99

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Brooks Brothers Shirt Men's 15 Blue Traditional Non Iron All Cotton Preppy Solid
Brooks Brothers Shirt Men's 15 Blue Traditional Non Iron All Cotton Preppy Solid

$10.38

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Ralph Lauren Blue Striped Long Sleeve Button Up Shirt Men’s Sz 15 Preppy
Ralph Lauren Blue Striped Long Sleeve Button Up Shirt Men’s Sz 15 Preppy

$23.00

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Polo Ralph Lauren Shirt Adult 15 32/33 Button Up Oxford Long Sleeve Preppy Mens
Polo Ralph Lauren Shirt Adult 15 32/33 Button Up Oxford Long Sleeve Preppy Mens

$16.99

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Vtg 1976 I'd Rather Be Sailing Needlepoint Art Green Blue 15x15" Preppy Nautical
Vtg 1976 I'd Rather Be Sailing Needlepoint Art Green Blue 15x15" Preppy Nautical

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Brooks Brothers Shirt Mens 15 Blue White Stripes Logo Button Up Casual Preppy
Brooks Brothers Shirt Mens 15 Blue White Stripes Logo Button Up Casual Preppy

$24.85

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Brooks Brothers Shirt Mens Adult 15 White Blue Stripes Button Up Preppy Regent
Brooks Brothers Shirt Mens Adult 15 White Blue Stripes Button Up Preppy Regent

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SuitSupply Button Shirt 15 White Blue Preppy Outdoors Formal Dress 38 Traveler
SuitSupply Button Shirt 15 White Blue Preppy Outdoors Formal Dress 38 Traveler

$31.02

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Brooks Brothers Men's 15 Slim Fit Shirt Non-Iron Button Down Blue Plaid Preppy
Brooks Brothers Men's 15 Slim Fit Shirt Non-Iron Button Down Blue Plaid Preppy

$5.99

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Charles Tyrwhitt Shirt Men's 15/5 33 White Pink Blue Preppy Micro Oxford Gingham
Charles Tyrwhitt Shirt Men's 15/5 33 White Pink Blue Preppy Micro Oxford Gingham

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Ralph Lauren Shirt Mens 15 32/33 Classic Fit Blue White Black Plaid Pony Preppy
Ralph Lauren Shirt Mens 15 32/33 Classic Fit Blue White Black Plaid Pony Preppy

$14.99

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Tallia Men Shirt Medium 15 1/2 Red Blue Classic Paisley Button Up Casual Preppy
Tallia Men Shirt Medium 15 1/2 Red Blue Classic Paisley Button Up Casual Preppy

$11.93

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Vintage Brooks Brothers Makers Button Up Shirt 15 - 35 Blue White Preppy Dress
Vintage Brooks Brothers Makers Button Up Shirt 15 - 35 Blue White Preppy Dress

$31.02

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LL Bean Green Plaid Oxford 15-34 OCBD Button Down Ivy Preppy USA
LL Bean Green Plaid Oxford 15-34 OCBD Button Down Ivy Preppy USA

$14.00

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Vintage Brooks Brothers Shirt Mens 15-34 Blue Slim Fit Classiccore Preppy Casual
Vintage Brooks Brothers Shirt Mens 15-34 Blue Slim Fit Classiccore Preppy Casual

$49.79

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Brooks Brothers Shirt Mens 15 1/2 x 32 Blue Plaid Button Up Office Preppy Down
Brooks Brothers Shirt Mens 15 1/2 x 32 Blue Plaid Button Up Office Preppy Down

$8.99

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David Donahue Long Sleeve Dress Shirt Men's 15 Plaid Preppy Cotton
David Donahue Long Sleeve Dress Shirt Men's 15 Plaid Preppy Cotton

$25.00

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Psycho Bunny Shirt Mens 15 Pink Button Up Preppy Casual Lightweight Logo
Psycho Bunny Shirt Mens 15 Pink Button Up Preppy Casual Lightweight Logo

$34.85

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Charles Tyrwhitt Shirt Mens 15 33 Blue Stripe Long Sleeve Button Up Preppy
Charles Tyrwhitt Shirt Mens 15 33 Blue Stripe Long Sleeve Button Up Preppy

$19.64

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Vtg 90s Puritan Sailor Collar Modest Preppy Holiday Plaid Tea Corduroy Dress S
Vtg 90s Puritan Sailor Collar Modest Preppy Holiday Plaid Tea Corduroy Dress S

$55.00

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Ralph Lauren Mens 15 Medium Plaid Fit Classic Fit L/S Button Down Preppy
Ralph Lauren Mens 15 Medium Plaid Fit Classic Fit L/S Button Down Preppy

$21.11

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MIASTO OVAL ROUND READING GLASSES COLOR GREEN~MEDIUM~RX QTY MADE IN TAIWAN+3.00
MIASTO OVAL ROUND READING GLASSES COLOR GREEN~MEDIUM~RX QTY MADE IN TAIWAN+3.00

$29.95

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Preppy Retro Flowers iPhone Case For iPhone 15 Plus 14 Pro Max 12 13 Mini 11
Preppy Retro Flowers iPhone Case For iPhone 15 Plus 14 Pro Max 12 13 Mini 11

$24.99

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Polo by Ralph Lauren Sailboat Stretch Legging, Size XS, P 15 Preppy Luxury
Polo by Ralph Lauren Sailboat Stretch Legging, Size XS, P 15 Preppy Luxury

$35.00

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Chaps Ralph Lauren Dress Shirt Mens 15 32/33 Button Down Preppy Retro Flaws*
Chaps Ralph Lauren Dress Shirt Mens 15 32/33 Button Down Preppy Retro Flaws*

$11.80

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Polo Ralph Lauren Shirt Men 15 33 Pastel Pink Casual Button Down Preppy Pony
Polo Ralph Lauren Shirt Men 15 33 Pastel Pink Casual Button Down Preppy Pony

$25.88

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Banana Republic Dress Shirt Men 15 15.5 Medium - French Cuff Gray Striped Preppy
Banana Republic Dress Shirt Men 15 15.5 Medium - French Cuff Gray Striped Preppy

$17.99

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Ralph Lauren Shirt Men 15 Blue Button Up Flesh Pony Classic Fit Preppy Medium
Ralph Lauren Shirt Men 15 Blue Button Up Flesh Pony Classic Fit Preppy Medium

$18.99

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Ralph Lauren Shirt Mens 15 Medium Blue Check Classic Fit Career Casual Preppy
Ralph Lauren Shirt Mens 15 Medium Blue Check Classic Fit Career Casual Preppy

$12.50

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Preppy #One Men Hawaiian Long Sleeved Button Front Shirt M Multicolor 15-15 1/2
Preppy #One Men Hawaiian Long Sleeved Button Front Shirt M Multicolor 15-15 1/2

$9.99

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J Crew Shirt Mens 15 Blue White Stripes Preppy Casual Button Up Pocket
J Crew Shirt Mens 15 Blue White Stripes Preppy Casual Button Up Pocket

$22.85

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SuitSupply Button Shirt 15 Blue White Preppy Outdoor Casual Formal Prep 38 Mens
SuitSupply Button Shirt 15 Blue White Preppy Outdoor Casual Formal Prep 38 Mens

$36.62

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Green Ombre LOOPY iPhone 15 Pro Max Phone Case EUC Preppy Trendy
Green Ombre LOOPY iPhone 15 Pro Max Phone Case EUC Preppy Trendy

$23.00

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ETON Shirt Mens 15 / 38 Black Button Up Long Sleeve French Cuff Adult Preppy
ETON Shirt Mens 15 / 38 Black Button Up Long Sleeve French Cuff Adult Preppy

$17.99

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Buttoned Down Slim Shirt Men’s Size 15 36 Purple Check Preppy Supima Cotton
Buttoned Down Slim Shirt Men’s Size 15 36 Purple Check Preppy Supima Cotton

$15.68

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Ralph Lauren Shirt Mens 15 32/33 Plaid Yarmouth Button Down Preppy Pony Logo
Ralph Lauren Shirt Mens 15 32/33 Plaid Yarmouth Button Down Preppy Pony Logo

$13.39

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Manhattan VTG 100% Cotton Dress Shirt Made In USA 15" 32/33 Preppy Dark Achedmia
Manhattan VTG 100% Cotton Dress Shirt Made In USA 15" 32/33 Preppy Dark Achedmia

$17.00

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Polo Ralph Lauren Dress Shirt Mens 15 38 Blue Striped Classic Preppy Formal
Polo Ralph Lauren Dress Shirt Mens 15 38 Blue Striped Classic Preppy Formal

$16.99

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Brooks Brothers Shirt Mens 15 1/2 33 The Original Polo OCBD Oxford Cloth Button
Brooks Brothers Shirt Mens 15 1/2 33 The Original Polo OCBD Oxford Cloth Button

$21.88

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Polo Ralph Lauren Shirt Mens Adult 15 1/2 Yellow Stripes Button Up Casual Preppy
Polo Ralph Lauren Shirt Mens Adult 15 1/2 Yellow Stripes Button Up Casual Preppy

$24.85

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VINTAGE Ralph Lauren Shirt Men 15 Blue Button Down Flesh Pony Preppy Medium
VINTAGE Ralph Lauren Shirt Men 15 Blue Button Down Flesh Pony Preppy Medium

$13.99

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Manhattan VTG 100% Cotton Dress Shirt Made In USA 15" 32/33 Preppy Dark Achedmia
Manhattan VTG 100% Cotton Dress Shirt Made In USA 15" 32/33 Preppy Dark Achedmia

$20.00

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Brooks Brothers Shirt Mens 15 - 32 Blue Striped Button Down Traditional Preppy
Brooks Brothers Shirt Mens 15 - 32 Blue Striped Button Down Traditional Preppy

$18.88

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Tommy Hilfiger Patchwork Madras Two Handle Bag 15" Inch Wide Retro Preppy
Tommy Hilfiger Patchwork Madras Two Handle Bag 15" Inch Wide Retro Preppy

$24.99

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J Crew Flex Oxford Shirt Mens Medium 15-15.5 Green Long Sleeve Button Up Preppy
J Crew Flex Oxford Shirt Mens Medium 15-15.5 Green Long Sleeve Button Up Preppy

$22.05

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Ledbury Shirtmakers Blue Plaid Tailored Fit Button Down Shirt Size S 15 Preppy
Ledbury Shirtmakers Blue Plaid Tailored Fit Button Down Shirt Size S 15 Preppy

$14.16

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Brooks Brothers Shirt Mens 15 33 Button Down Long Sleeve Cotton Preppy Lot of 2
Brooks Brothers Shirt Mens 15 33 Button Down Long Sleeve Cotton Preppy Lot of 2

$41.00

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Brooks Brothers Shirt Mens 15 Light Yellow Madison Button Up Preppy Modern NEW
Brooks Brothers Shirt Mens 15 Light Yellow Madison Button Up Preppy Modern NEW

$26.55

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Brooks Brothers Shirt Mens 15 1/2 White Black Plaid Button Up Casual Preppy
Brooks Brothers Shirt Mens 15 1/2 White Black Plaid Button Up Casual Preppy

$24.85

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Brooks Brothers Shirt Men 15 33 Pink Casual Button Down Milano Preppy Plaid
Brooks Brothers Shirt Men 15 33 Pink Casual Button Down Milano Preppy Plaid

$29.88

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Turnbull & Asser Shirt Mens 15 White Blue French Cuff Cotton England Preppy
Turnbull & Asser Shirt Mens 15 White Blue French Cuff Cotton England Preppy

$42.00

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Polo Ralph Lauren Shirt Men's XL Polo Blue Custom Fit Big Pony Preppy RL15
Polo Ralph Lauren Shirt Men's XL Polo Blue Custom Fit Big Pony Preppy RL15

$29.99

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Vintage Gitman Bros Shirt Mens 15 33 Blue Button Preppy Cotton USA Classic A2
Vintage Gitman Bros Shirt Mens 15 33 Blue Button Preppy Cotton USA Classic A2

$21.00

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Ermenegildo Zegna Shirt Mens 40-15 3/4 Blue Striped Trofeo Preppy Work Business
Ermenegildo Zegna Shirt Mens 40-15 3/4 Blue Striped Trofeo Preppy Work Business

$48.88

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TEST. PATRICIA NASH Satchel Heritage
TEST. PATRICIA NASH Satchel Heritage

$26.99

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Brooks Brothers Regent Shirt Mens Medium 15 Blue Geometric Dress Casual Preppy
Brooks Brothers Regent Shirt Mens Medium 15 Blue Geometric Dress Casual Preppy

$14.98

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Tommy Hilfiger Shirt Mens Medium 15-15.5 Blue Classic Preppy Business Basic
Tommy Hilfiger Shirt Mens Medium 15-15.5 Blue Classic Preppy Business Basic

$9.84

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Eton Contemporary Dress Shirt Mens 15 (38) Geometric Limited Edition Gold Preppy
Eton Contemporary Dress Shirt Mens 15 (38) Geometric Limited Edition Gold Preppy

$74.95

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Ralph Lauren Polo Shirt Mens 15 32 33 Green Gingham Classic Fit Purple Pony VTG
Ralph Lauren Polo Shirt Mens 15 32 33 Green Gingham Classic Fit Purple Pony VTG

$18.00

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Bonobos Shirt Men 15 1/2 34 Blue Button Up Slim Fit Wrinkle Free Casual Preppy
Bonobos Shirt Men 15 1/2 34 Blue Button Up Slim Fit Wrinkle Free Casual Preppy

$13.30

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Vintage Gap Corduroy Pants Size 15/16 Beige Preppy Eighties Retro Baggy Pleated
Vintage Gap Corduroy Pants Size 15/16 Beige Preppy Eighties Retro Baggy Pleated

$34.85

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Tommy Hilfiger Madras Plaid Canvas Tote Bag Purse Red Blue Preppy Flannel
Tommy Hilfiger Madras Plaid Canvas Tote Bag Purse Red Blue Preppy Flannel

$16.99

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Brooks Brothers Shirt Mens 15 Red Blue Plaid Button Up Casual Preppy Regent
Brooks Brothers Shirt Mens 15 Red Blue Plaid Button Up Casual Preppy Regent

$24.85

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Ralph Lauren Shirt Mens Adult 15 1/2 White Blue Plaid Button Up Yarmouth Preppy
Ralph Lauren Shirt Mens Adult 15 1/2 White Blue Plaid Button Up Yarmouth Preppy

$24.85

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Canali Shirt Mens 38 15 Blue Plaid Made In Italy Cotton Long Sleeve Dress Preppy
Canali Shirt Mens 38 15 Blue Plaid Made In Italy Cotton Long Sleeve Dress Preppy

$18.00

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Retro Preppy Striped Polo XS/S 15x24 Orange
Retro Preppy Striped Polo XS/S 15x24 Orange

$28.79

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Ledbury Dress Shirt Mens 15 1/2 Colorful Check Check Button Up Preppy Classic
Ledbury Dress Shirt Mens 15 1/2 Colorful Check Check Button Up Preppy Classic

$22.97

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Ralph Lauren Shirt Men Size 15 Blue Cotton Long Sleeve Button Up Preppy Office.
Ralph Lauren Shirt Men Size 15 Blue Cotton Long Sleeve Button Up Preppy Office.

$15.99

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Vintage Anchor Blue Plaid Lightweight Casual Preppy Beach Casual Shorts 15 USA
Vintage Anchor Blue Plaid Lightweight Casual Preppy Beach Casual Shorts 15 USA

$11.11

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Brooks Brothers Shirt Mens 15 1/2 Blue Pink Stripes Button Up Casual Preppy
Brooks Brothers Shirt Mens 15 1/2 Blue Pink Stripes Button Up Casual Preppy

$24.85

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Brooks Brothers Shirt Mens 15-34 Blue Button Up Long Sleeve Stripe Cotton
Brooks Brothers Shirt Mens 15-34 Blue Button Up Long Sleeve Stripe Cotton

$19.99

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No Boundaries Dress Youth Girls XL 15-17 Cream Cottagecore Floral Preppy Top
No Boundaries Dress Youth Girls XL 15-17 Cream Cottagecore Floral Preppy Top

$6.52

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Polo Ralph Lauren Shirt Mens 15-32 Yellow Oxford Yarmouth Color Pony Preppy
Polo Ralph Lauren Shirt Mens 15-32 Yellow Oxford Yarmouth Color Pony Preppy

$17.99

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David Donahue Shirt Men 15 32-32 Lavender Purple Check Button Up Preppy Casual
David Donahue Shirt Men 15 32-32 Lavender Purple Check Button Up Preppy Casual

$19.88

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Burberrys of London Mens Dress Shirt Size 15-32/33 Blue preppy business casual
Burberrys of London Mens Dress Shirt Size 15-32/33 Blue preppy business casual

$24.50

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Ralph Lauren Button Up Collar Shirt Long Sleeve Pony Logo Yarmouth Gray Size 15
Ralph Lauren Button Up Collar Shirt Long Sleeve Pony Logo Yarmouth Gray Size 15

$7.20

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Brooks Brothers Shirt 15-32 Pink White Check Cotton Button Down
Brooks Brothers Shirt 15-32 Pink White Check Cotton Button Down

$20.00

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Ralph Lauren Shirt Mens 15 32/33 Multicolor Plaid Button Down Classic Preppy
Ralph Lauren Shirt Mens 15 32/33 Multicolor Plaid Button Down Classic Preppy

$19.83

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Brooks Brothers Shirt Mens Medium 15 Pink Supima Oxford Button Up Made In USA
Brooks Brothers Shirt Mens Medium 15 Pink Supima Oxford Button Up Made In USA

$32.79

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Maurices Distressed Stretch Jeans Womens Preppy Grunge Embroidered Pockets 15/16
Maurices Distressed Stretch Jeans Womens Preppy Grunge Embroidered Pockets 15/16

$14.97

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Polo Ralph Lauren Button Up Shirt ANDREW Long Yellow Plaid Preppy Mens 15 1/2 M
Polo Ralph Lauren Button Up Shirt ANDREW Long Yellow Plaid Preppy Mens 15 1/2 M

$13.67

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Brooks Brothers Shirt 15 1/2-32 Blue Stripe Classic Preppy Office Business
Brooks Brothers Shirt 15 1/2-32 Blue Stripe Classic Preppy Office Business

$14.88

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Bonobos Shirt Mens 15 Purple Tailored Business Casual Office Preppy Stretch
Bonobos Shirt Mens 15 Purple Tailored Business Casual Office Preppy Stretch

$21.84

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Brooks Brothers Button Up Shirt Adult Medium 15 Blue Casual Preppy USA Mens
Brooks Brothers Button Up Shirt Adult Medium 15 Blue Casual Preppy USA Mens

$7.00

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Suitsupply Shirt Mens 40-15 3/4 Two Ply Cotton Preppy Workwear Office Casual
Suitsupply Shirt Mens 40-15 3/4 Two Ply Cotton Preppy Workwear Office Casual

$18.30

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Banana Republic Shirt Men Medium 15/15.5 Purple Striped Slim Fit Preppy Adult
Banana Republic Shirt Men Medium 15/15.5 Purple Striped Slim Fit Preppy Adult

$11.33

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Ralph Lauren Shirt Men Button Classic Fit Green Purple Striped Preppy Coastal 15
Ralph Lauren Shirt Men Button Classic Fit Green Purple Striped Preppy Coastal 15

$13.39

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Polo Ralph Lauren Long Sleeve Button Shirt Men's Size 15 Pink Flesh Pony Striped
Polo Ralph Lauren Long Sleeve Button Shirt Men's Size 15 Pink Flesh Pony Striped

$14.41

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Ralph Lauren Shirt Pink Button Down Flesh Pony Logo Men 15 Classic Fit Preppy
Ralph Lauren Shirt Pink Button Down Flesh Pony Logo Men 15 Classic Fit Preppy

$20.00

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Psycho Bunny Shirt Mens 15 32/33 Gray Stretch Lycr Formal Business Casual Preppy
Psycho Bunny Shirt Mens 15 32/33 Gray Stretch Lycr Formal Business Casual Preppy

$12.93

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NEW Vintage 80's Wool Blazer and Skirt Suit Set in Dark Charcoal Gray Pinstripe
NEW Vintage 80's Wool Blazer and Skirt Suit Set in Dark Charcoal Gray Pinstripe

$85.00

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White High Open Collar Highlighted Navy Blue Piping 100% Cotton Men Preppy Shirt
White High Open Collar Highlighted Navy Blue Piping 100% Cotton Men Preppy Shirt

$130.50

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