original-preppy-clothes

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Vintage 90s Ivy Club Classics Plaid Pinafore Dress Midi Grunge Preppy Overall L
Vintage 90s Ivy Club Classics Plaid Pinafore Dress Midi Grunge Preppy Overall L

$39.88

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Vintage Laura Ashley White Cotton Dress Sailor Collar Nautical Preppy Pockets
Vintage Laura Ashley White Cotton Dress Sailor Collar Nautical Preppy Pockets

$112.10

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Abercrombie Authentic Originals Rugby Cloth Shirt Womens S Stripe Preppy Cropped
Abercrombie Authentic Originals Rugby Cloth Shirt Womens S Stripe Preppy Cropped

$17.97

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Vtg 80s 90s Preppy Polka Dot Femme Cage Back Uptown Girl Collared Midi Dress S/M
Vtg 80s 90s Preppy Polka Dot Femme Cage Back Uptown Girl Collared Midi Dress S/M

$65.00

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Vtg 90s Red Pretty Woman Preppy Huge Polka Dot Rayon Swing Trad Wife Dress M/L
Vtg 90s Red Pretty Woman Preppy Huge Polka Dot Rayon Swing Trad Wife Dress M/L

$75.00

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Vtg 80s Preppy New Wave Split Puff Slv Pastel Hipster Full Skirt Shirt Dress S/M
Vtg 80s Preppy New Wave Split Puff Slv Pastel Hipster Full Skirt Shirt Dress S/M

$85.00

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Vintage Styleworks Corduroy Shirt Dress Womens 10 Blue Cotton Cottagecore Preppy
Vintage Styleworks Corduroy Shirt Dress Womens 10 Blue Cotton Cottagecore Preppy

$23.98

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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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Vtg 90s Preppy Mall Grunge Plaid EXPO Wiggle Stretch Crinkle Empire Dress S/M
Vtg 90s Preppy Mall Grunge Plaid EXPO Wiggle Stretch Crinkle Empire Dress S/M

$75.00

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Vtg 80s Preppy New Wave Secretary Office Colorblock Puff Sleeve Wiggle Dress M
Vtg 80s Preppy New Wave Secretary Office Colorblock Puff Sleeve Wiggle Dress M

$75.00

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Vtg 80s Granny Floral Preppy Garden Party Trad Wife Full Skirt Belted Dress M/L
Vtg 80s Granny Floral Preppy Garden Party Trad Wife Full Skirt Belted Dress M/L

$95.00

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Vintage 90s Erika floral midi dress size PM peasant cottagecore preppy modest
Vintage 90s Erika floral midi dress size PM peasant cottagecore preppy modest

$30.00

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Vintage Preppy One Step Up Hand Knit White Cardigan Large
Vintage Preppy One Step Up Hand Knit White Cardigan Large

$50.00

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Vtg 1970s Whimsicals Tennis Mini Dress Colorful Preppy Old Money Palm Royale S
Vtg 1970s Whimsicals Tennis Mini Dress Colorful Preppy Old Money Palm Royale S

$78.00

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Women's Vintage Sailor Skirt and Top, Preppy, Handcrafted
Women's Vintage Sailor Skirt and Top, Preppy, Handcrafted

$15.00

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Robbie Sport USA Vtg 80s Acrylic Preppy Grandma Sweater Womens Medium
Robbie Sport USA Vtg 80s Acrylic Preppy Grandma Sweater Womens Medium

$12.32

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Collars & Co Original Dress Collar Polo Shirt Mens M Blue Checked Golf Preppy
Collars & Co Original Dress Collar Polo Shirt Mens M Blue Checked Golf Preppy

$28.88

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Vintage Reyn Spooner Corduroy Jumper Dress
Vintage Reyn Spooner Corduroy Jumper Dress

$50.00

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Vintage Jockey Cable Knit Ivory Preppy V-Neck Sweater Size Mens Large
Vintage Jockey Cable Knit Ivory Preppy V-Neck Sweater Size Mens Large

$25.00

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Preppy vintage boy’s tennis v-neck knit sweater, long-sleeved navy blue
Preppy vintage boy’s tennis v-neck knit sweater, long-sleeved navy blue

$23.00

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Vintage 80s Red Knit Sweater Size Large Preppy Colorblock Irish Cotton Crewneck
Vintage 80s Red Knit Sweater Size Large Preppy Colorblock Irish Cotton Crewneck

$24.98

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Vintage Lacoste Dress 70s Red Navy Blue Stripes Preppy Trim Button Front S/M
Vintage Lacoste Dress 70s Red Navy Blue Stripes Preppy Trim Button Front S/M

$90.00

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Collars & Co Original Dress Collar Polo Shirt Mens M Purple Golf Stretch Preppy
Collars & Co Original Dress Collar Polo Shirt Mens M Purple Golf Stretch Preppy

$28.88

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Vtg 90s British Preppy Holiday Plaid Velvet Peter Pan Cottage Riding Dress M/L
Vtg 90s British Preppy Holiday Plaid Velvet Peter Pan Cottage Riding Dress M/L

$65.00

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Vintage Polo Ralph Lauren Steiff Bear “The Preppy Bear” From 1991
Vintage Polo Ralph Lauren Steiff Bear “The Preppy Bear” From 1991

$685.00

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Vintage 90s Pink Pretty Woman Preppy Polka Dot Uptown Girl Strappy Midi Dress M
Vintage 90s Pink Pretty Woman Preppy Polka Dot Uptown Girl Strappy Midi Dress M

$125.00

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Vintage Scooter Mod Micro Mini Dress Knit Go Go Disco Uniform Preppy Short Frock
Vintage Scooter Mod Micro Mini Dress Knit Go Go Disco Uniform Preppy Short Frock

$51.30

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Vtg 60s-Style Preppy Sheath Dress-Lilly P Look-by Jessica Howard-Fully Lined-6
Vtg 60s-Style Preppy Sheath Dress-Lilly P Look-by Jessica Howard-Fully Lined-6

$14.99

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Vintage 16 Linen Pink Plaid Maxi Dress Ruffle Preppy Cottagecore Quiet Luxury
Vintage 16 Linen Pink Plaid Maxi Dress Ruffle Preppy Cottagecore Quiet Luxury

$57.80

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Vintage Size 6 Dress Mini 90s Academia Bow Sailorcore Twee Preppy Country Club
Vintage Size 6 Dress Mini 90s Academia Bow Sailorcore Twee Preppy Country Club

$38.00

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Vtg 80s Victorian Collar Preppy Floral Wallpaper Cottagecore Day Casual Dress S
Vtg 80s Victorian Collar Preppy Floral Wallpaper Cottagecore Day Casual Dress S

$65.00

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50s Vintage Mr Mort Button Dress Black Nautical Preppy Short Sleeve Knee Length
50s Vintage Mr Mort Button Dress Black Nautical Preppy Short Sleeve Knee Length

$80.00

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Vtg 60s Preppy Mod Plaid Wool Peter Pan 2 pc Boxy Jacket Skirt Dress Suit S/M
Vtg 60s Preppy Mod Plaid Wool Peter Pan 2 pc Boxy Jacket Skirt Dress Suit S/M

$95.00

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Vintage 60s Preppy Mod Academia Knee length Collared Dress by Maggi Stover
Vintage 60s Preppy Mod Academia Knee length Collared Dress by Maggi Stover

$117.00

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VTG Y2K Preppy Babydoll Dress Gray Cropped Cardigan Modest Maxi Skirt 1990’s L
VTG Y2K Preppy Babydoll Dress Gray Cropped Cardigan Modest Maxi Skirt 1990’s L

$20.96

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80s Vintage Laura Ashley Corduroy Dress Floral Cottage Preppy Puff Sleeve
80s Vintage Laura Ashley Corduroy Dress Floral Cottage Preppy Puff Sleeve

$125.00

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NWOT Lands End forest green cotton turtleneck dress XL vintage 90s preppy
NWOT Lands End forest green cotton turtleneck dress XL vintage 90s preppy

$36.88

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Vintage 1970’s 1980’s A-line Sleeveless Popover Dress Size Medium Preppy
Vintage 1970’s 1980’s A-line Sleeveless Popover Dress Size Medium Preppy

$20.00

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VNT 90s Gap Authentic Fit Striped Dress Shirt 100% Cotton Med Blue White Preppy
VNT 90s Gap Authentic Fit Striped Dress Shirt 100% Cotton Med Blue White Preppy

$16.00

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Vintage Quillmark PREPPY Notebook 1980s Green Prep Gator Journal Ivy Style Trad
Vintage Quillmark PREPPY Notebook 1980s Green Prep Gator Journal Ivy Style Trad

$62.99

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Preppy Plaid Riding Princess Mermaid Peter Pan Midi Dress S
Preppy Plaid Riding Princess Mermaid Peter Pan Midi Dress S

$9.09

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Vintage 80s Candy Red Preppy Linen Huge Button Colorblock Volup Dress L/XL Tall
Vintage 80s Candy Red Preppy Linen Huge Button Colorblock Volup Dress L/XL Tall

$95.00

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NWT Collars & Co Men's Medium Original Dress Collar Polo Shirt Thin Blue Check
NWT Collars & Co Men's Medium Original Dress Collar Polo Shirt Thin Blue Check

$43.21

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Cabbage Patch Kids Doll, VTG 1986 Curly Blonde Hair Preppie Girl Blue Eyes HM#9
Cabbage Patch Kids Doll, VTG 1986 Curly Blonde Hair Preppie Girl Blue Eyes HM#9

$30.00

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Vintage 80s Preppy Flamingo Pink Ringer Full Skirt Shirtwaist Wrap Tea Dress M/L
Vintage 80s Preppy Flamingo Pink Ringer Full Skirt Shirtwaist Wrap Tea Dress M/L

$55.00

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Vtg 70s Preppy Pussy Bow Sheer Bishop Powder Blue Secretary Shirtwaist Dress L
Vtg 70s Preppy Pussy Bow Sheer Bishop Powder Blue Secretary Shirtwaist Dress L

$125.00

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Vintage 80s 90s Madras Plaid Cotton India Preppy Boho Cottage Jumper Dress S/M
Vintage 80s 90s Madras Plaid Cotton India Preppy Boho Cottage Jumper Dress S/M

$48.00

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Vintage 90s Rampage Preppy Punk Dress Tight Plaid Mini Grunge Flannel Look S
Vintage 90s Rampage Preppy Punk Dress Tight Plaid Mini Grunge Flannel Look S

$65.00

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Vintage Genny Versace Linen Dress French Preppy Old Money 90s Quiet Luxury
Vintage Genny Versace Linen Dress French Preppy Old Money 90s Quiet Luxury

$55.00

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Vintage Dress 6 Medium Brown Plaid A-Line Pleated Mod Preppy Librarian Academia
Vintage Dress 6 Medium Brown Plaid A-Line Pleated Mod Preppy Librarian Academia

$34.00

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Vintage Lanz Original Red Rose Print Dress Preppy Navy Blue Pockets Midi Size 8
Vintage Lanz Original Red Rose Print Dress Preppy Navy Blue Pockets Midi Size 8

$56.05

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Vintage Leslie Fay Knit Sweater Dress Red Preppy 80s 90s Teacher Christmas sz L
Vintage Leslie Fay Knit Sweater Dress Red Preppy 80s 90s Teacher Christmas sz L

$22.32

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Vtg 90s Preppy Punk Reality Bites Tieback Babydoll Floral Rayon Midi Dress S/M
Vtg 90s Preppy Punk Reality Bites Tieback Babydoll Floral Rayon Midi Dress S/M

$65.00

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1981 Jordache Preppy Fashions Outfit -Blouse and Skirt
1981 Jordache Preppy Fashions Outfit -Blouse and Skirt

$14.00

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Vintage KONO 1980s Floral Drop Waist Cottagecore Dress Pleated Size 7/8 Preppy
Vintage KONO 1980s Floral Drop Waist Cottagecore Dress Pleated Size 7/8 Preppy

$26.00

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Vintage 90s R&K Originals Dress Women 8 Black Yellow Floral Back Tie Sleeveless
Vintage 90s R&K Originals Dress Women 8 Black Yellow Floral Back Tie Sleeveless

$24.98

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Vtg Nautical Sailboat Sundress 80s Preppy Black Striped Nautical Boat Sun Dress
Vtg Nautical Sailboat Sundress 80s Preppy Black Striped Nautical Boat Sun Dress

$55.10

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Vintage 80s Sears Preppy Geek Chevron Sundress Striped Casual T-Shirt Dress S/M
Vintage 80s Sears Preppy Geek Chevron Sundress Striped Casual T-Shirt Dress S/M

$95.00

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Vtg 90s Pretty Woman Preppy Polka Dot Uptown Girl Midi Rayon Swing Dress XS/S
Vtg 90s Pretty Woman Preppy Polka Dot Uptown Girl Midi Rayon Swing Dress XS/S

$75.00

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Vtg 90s Girly Preppy Punk Babydoll Floral Kinderwhore Rayon Pocket Dress L/XL
Vtg 90s Girly Preppy Punk Babydoll Floral Kinderwhore Rayon Pocket Dress L/XL

$45.00

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Vintage 80's Gingham Dress - Size Small
Vintage 80's Gingham Dress - Size Small

$25.00

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Vtg Pastel Plaid Green Velvet Set Party Dress Bolero Size 12 Whimsigoth Preppy
Vtg Pastel Plaid Green Velvet Set Party Dress Bolero Size 12 Whimsigoth Preppy

$22.00

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Vintage 70s Navy Blue + White Polka Dot Preppy Button Down Long Sleeve Dress M
Vintage 70s Navy Blue + White Polka Dot Preppy Button Down Long Sleeve Dress M

$36.00

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1970s Vintage Red White Blue Gingham Preppy Sleeveless Mini Dress Size ~Small
1970s Vintage Red White Blue Gingham Preppy Sleeveless Mini Dress Size ~Small

$35.00

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Vintage R & K Originals Dress Womens 14 Brown Shirtdress Office Weekend Academia
Vintage R & K Originals Dress Womens 14 Brown Shirtdress Office Weekend Academia

$23.62

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Womens Lauren Original Clothing Supply Plaid Pastel Rain Jacket Sz M NWOT
Womens Lauren Original Clothing Supply Plaid Pastel Rain Jacket Sz M NWOT

$26.99

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Vintage Schrader Secretary Dress Size 12 Pleated Paisley 1980s Preppy
Vintage Schrader Secretary Dress Size 12 Pleated Paisley 1980s Preppy

$20.70

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Doll Clothes Playmates Toys Ever Girl Fashion Preppy Outfit Shoes Purse NOS 2005
Doll Clothes Playmates Toys Ever Girl Fashion Preppy Outfit Shoes Purse NOS 2005

$16.95

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Vintage 90s Preppy Punk Hipster Grannycore Rayon Midi Floral Romantic Dress S/M
Vintage 90s Preppy Punk Hipster Grannycore Rayon Midi Floral Romantic Dress S/M

$65.00

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True VTG 1960s 1970s Polyester Preppy Maxi Dress Big Collar Mid-century Plaid 12
True VTG 1960s 1970s Polyester Preppy Maxi Dress Big Collar Mid-century Plaid 12

$64.95

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Vtg Susanna Dress Womens 8 Plaid Secretary Peplum Belted Preppy Classic Modest
Vtg Susanna Dress Womens 8 Plaid Secretary Peplum Belted Preppy Classic Modest

$69.97

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Vintage 80s Nautical Preppy Mini Dress by Brooks Brothers
Vintage 80s Nautical Preppy Mini Dress by Brooks Brothers

$50.00

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Vtg 80s Uptown Girl Preppy Shirtwaist Lemon Huge Polka Dot Volup Midi Dress L/XL
Vtg 80s Uptown Girl Preppy Shirtwaist Lemon Huge Polka Dot Volup Midi Dress L/XL

$95.00

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Vintage 70s Vested Gentress Preppy Kitsch Novelty Print Snail Shift Sun Dress S
Vintage 70s Vested Gentress Preppy Kitsch Novelty Print Snail Shift Sun Dress S

$75.00

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Vtg 70s Preppy Pussy Bow Pop Art Garden Party 2pc Puff Sleeve Peplum Top Dress M
Vtg 70s Preppy Pussy Bow Pop Art Garden Party 2pc Puff Sleeve Peplum Top Dress M

$125.00

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Vintage Jeffrey & Dara Black Wrap Dress Animal Print Trim sz 8 Preppy
Vintage Jeffrey & Dara Black Wrap Dress Animal Print Trim sz 8 Preppy

$37.00

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Vintage Shetland Wool V-Neck Sweater L Soft Preppy Rugby Blue Green Gold Stripes
Vintage Shetland Wool V-Neck Sweater L Soft Preppy Rugby Blue Green Gold Stripes

$16.88

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Barbie Clone Preppy Fashion Striped Top Lilac Pleated Skirt Shoes Backpack
Barbie Clone Preppy Fashion Striped Top Lilac Pleated Skirt Shoes Backpack

$10.99

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Original Penguin 16.5 34/35 Blue Longsleeve Heritage Slim Fit Preppy *butto
Original Penguin 16.5 34/35 Blue Longsleeve Heritage Slim Fit Preppy *butto

$17.99

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LANDS END Original Oxford No Iron Shirt Mens M 15.5 Pinpoint Preppy 100% Cotton
LANDS END Original Oxford No Iron Shirt Mens M 15.5 Pinpoint Preppy 100% Cotton

$12.85

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Vintage 1970s Christmas Plaid Preppy Farah Mens Dress Trousers Red Navy 32 x 29
Vintage 1970s Christmas Plaid Preppy Farah Mens Dress Trousers Red Navy 32 x 29

$48.00

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Vintage 1980s Preppy Plaid Vest Holiday Riding Dress S/M
Vintage 1980s Preppy Plaid Vest Holiday Riding Dress S/M

$45.00

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J. Crew Original Beachwear Gingham Drop Waist V Neck Tunic Dress Size XS
J. Crew Original Beachwear Gingham Drop Waist V Neck Tunic Dress Size XS

$19.99

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NWT 1950s USA Brooks Brothers Makers 16 34 Sanforized off white OCBD shirt
NWT 1950s USA Brooks Brothers Makers 16 34 Sanforized off white OCBD shirt

$299.67

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An Original Penguin Polo Shirt Men’s Short Sleeve White Logo Golf Preppy Medium
An Original Penguin Polo Shirt Men’s Short Sleeve White Logo Golf Preppy Medium

$24.99

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J Crew Factory Original Schoolboy Blue Wool Blend Preppy Blazer Jacket Womens 14
J Crew Factory Original Schoolboy Blue Wool Blend Preppy Blazer Jacket Womens 14

$39.99

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Vintage Yellow Stripe Sunny Dress Sz 8 Preppy Summer
Vintage Yellow Stripe Sunny Dress Sz 8 Preppy Summer

$24.99

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Vintage Laura Ashley Corduroy Dress Drop Waist Green Holiday Party Boho Preppy 6
Vintage Laura Ashley Corduroy Dress Drop Waist Green Holiday Party Boho Preppy 6

$104.50

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Vtg 90s Corset Back Pretty Woman Preppy Polka Dot Uptown Girl Rayon Slip Dress M
Vtg 90s Corset Back Pretty Woman Preppy Polka Dot Uptown Girl Rayon Slip Dress M

$65.00

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Vintage 70s Preppy Mini Dress Pink Plaid Argyle patterned Collared Dress Sears
Vintage 70s Preppy Mini Dress Pink Plaid Argyle patterned Collared Dress Sears

$72.00

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Preppy Classic Vtg 90s Liz Claiborne Thick Heavy Dress Cardigan Sweater Coat S
Preppy Classic Vtg 90s Liz Claiborne Thick Heavy Dress Cardigan Sweater Coat S

$39.98

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Vintage Plaid Sleeveless Girls' Dress with Pockets - Size 8 - School Preppy
Vintage Plaid Sleeveless Girls' Dress with Pockets - Size 8 - School Preppy

$24.95

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Vtg 80s Mall Rat Volup Button Back Jumper TShirt Drop Waist Preppy Dress XL/XXL
Vtg 80s Mall Rat Volup Button Back Jumper TShirt Drop Waist Preppy Dress XL/XXL

$125.00

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Teddy Bear Plush with Glasses Woodland Forest Preppy Stuffed Animal
Teddy Bear Plush with Glasses Woodland Forest Preppy Stuffed Animal

$19.79

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Vtg 80s Romantic English Rose Preppy Garden Party Trad Wife Full Skirt Dress M/L
Vtg 80s Romantic English Rose Preppy Garden Party Trad Wife Full Skirt Dress M/L

$125.00

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vintage 1980s Moody Floral Sheath Pleated wrap Dress dark academia preppy
vintage 1980s Moody Floral Sheath Pleated wrap Dress dark academia preppy

$17.00

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LACOSTE Pants 48 X 32 Khaki Preppy Casual Golf Office VTG Made In Peru
LACOSTE Pants 48 X 32 Khaki Preppy Casual Golf Office VTG Made In Peru

$23.99

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Vintage 90s Limited Houndstooth Dress Preppy Tailored Collegiate Office Size 14
Vintage 90s Limited Houndstooth Dress Preppy Tailored Collegiate Office Size 14

$44.00

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80s 90s vintage floral dress preppy twee straps buttons abstract flower art
80s 90s vintage floral dress preppy twee straps buttons abstract flower art

$55.00

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50s vintage polkadot tea dress pleated ruffle cotton Medium preppy twee pattern
50s vintage polkadot tea dress pleated ruffle cotton Medium preppy twee pattern

$80.00

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