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Old Navy Y2K Babydoll V Neck Sweater Vest Size 2XL Tan Retro Minimal Preppy
Old Navy Y2K Babydoll V Neck Sweater Vest Size 2XL Tan Retro Minimal Preppy

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90s Vtg Cable Knit Cricket Tennis Sweater Sz Med Green Preppy Old Navy Ramie
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Old Navy blue patchwork hand sewn preppy wabi sabi flat front shorts 34
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Old Navy Jeans Mens 36x34 Blue Bootcut Straight Dark Wash Denim Stretch Preppy
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Old Navy Vintage Y2K Single Button Preppy Pleated Blazer Jacket - Beige Wmns S
Old Navy Vintage Y2K Single Button Preppy Pleated Blazer Jacket - Beige Wmns S

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90s Preppy Old Money Beige Plaid Boucle Jacket
90s Preppy Old Money Beige Plaid Boucle Jacket

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Old Navy Sweater Mens Small Gray Chunky Ribbed Fisherman Knit Old Money Preppy
Old Navy Sweater Mens Small Gray Chunky Ribbed Fisherman Knit Old Money Preppy

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Old Navy Overalls Women's 8 Blue Denim Outdoors Workwear Preppy Y2kfashion
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Old Navy Cardigan Sweater Mens Tan Oatmeal Grandpa Preppy Chunk Knit Size Large
Old Navy Cardigan Sweater Mens Tan Oatmeal Grandpa Preppy Chunk Knit Size Large

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Mens NWT Old Navy Polo Shirt Navy Blue White Trim Sz M Classic Fit Casual Preppy
Mens NWT Old Navy Polo Shirt Navy Blue White Trim Sz M Classic Fit Casual Preppy

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Old Navy Gingham Top Women Medium Blue Cottagecore Colonial Preppy Peasant
Old Navy Gingham Top Women Medium Blue Cottagecore Colonial Preppy Peasant

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Polo Ralph Lauren Preppy Cable Knit Sweater Mens S White Crest Golf Old Money
Polo Ralph Lauren Preppy Cable Knit Sweater Mens S White Crest Golf Old Money

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Vintage Brooks Brothers Makers Preppy Old Money Silk Neck Tie Golfer Stripes
Vintage Brooks Brothers Makers Preppy Old Money Silk Neck Tie Golfer Stripes

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Vintage Old Navy Shorts Men 36 Tan Pleated Chino Eclectic Grandpa Dad Preppy Y2K
Vintage Old Navy Shorts Men 36 Tan Pleated Chino Eclectic Grandpa Dad Preppy Y2K

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Old Navy Vintage Polo Sweater Preppy Lambs Wool Angora Blend Size M
Old Navy Vintage Polo Sweater Preppy Lambs Wool Angora Blend Size M

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NEW Womens Button-Up Cardigan Sweater Ivory Soft XL Old Money Classic Preppy AYR
NEW Womens Button-Up Cardigan Sweater Ivory Soft XL Old Money Classic Preppy AYR

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Old Navy Top Women’s Medium M Blue White Gingham Check Seersucker Preppy Spring
Old Navy Top Women’s Medium M Blue White Gingham Check Seersucker Preppy Spring

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Old Navy Red Plaid Blouse XXL Split Neck Seersucker Popover Preppy Colorful NWT
Old Navy Red Plaid Blouse XXL Split Neck Seersucker Popover Preppy Colorful NWT

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Vintage Anne Klein Womens Wool Mohair Long Line Coat Size 10 Preppy Old Money
Vintage Anne Klein Womens Wool Mohair Long Line Coat Size 10 Preppy Old Money

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Old Navy Button Down Shirt Size XXL Striped Lightweight Nautical Preppy Casual
Old Navy Button Down Shirt Size XXL Striped Lightweight Nautical Preppy Casual

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Old Navy Houndstooth Coat Women's Size Medium Preppy Overcoat Classic Neutral
Old Navy Houndstooth Coat Women's Size Medium Preppy Overcoat Classic Neutral

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Old Navy Girls Sz S 6 Polka Dot Lightweight Dress 100% Rayon Preppy
Old Navy Girls Sz S 6 Polka Dot Lightweight Dress 100% Rayon Preppy

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Old Navy Cardigan NWOT Pink Heather Cable knit sweater preppy open front Size M
Old Navy Cardigan NWOT Pink Heather Cable knit sweater preppy open front Size M

$19.99

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Vintage Ralph Lauren Button Up Top 1x Quiet Luxury Academia Old Money Preppy
Vintage Ralph Lauren Button Up Top 1x Quiet Luxury Academia Old Money Preppy

$13.98

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Vintage Talbots Womens Wool Plaid Blazer Size 8P Three Button Preppy Old Money
Vintage Talbots Womens Wool Plaid Blazer Size 8P Three Button Preppy Old Money

$29.00

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Polo Ralph Lauren Shirt Mens L Blue Striped Seersucker Preppy Old Money 90's
Polo Ralph Lauren Shirt Mens L Blue Striped Seersucker Preppy Old Money 90's

$12.49

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Vintage 80s YSL Wool Herringbone Tweed Blazer Old Money Preppy Equestrian
Vintage 80s YSL Wool Herringbone Tweed Blazer Old Money Preppy Equestrian

$60.00

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Vintage OLD NAVY Camel Cashmere Mock Neck Sweater Women’s Gold Label Size Large
Vintage OLD NAVY Camel Cashmere Mock Neck Sweater Women’s Gold Label Size Large

$25.00

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Bankers Club Tartan Plaid Checkered Women Skirt Blazer 2pc Preppy Old Money
Bankers Club Tartan Plaid Checkered Women Skirt Blazer 2pc Preppy Old Money

$71.42

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Old Navy Pants Size 2 Petite Office Academia Preppy Plaid Windowpane Check Y2K
Old Navy Pants Size 2 Petite Office Academia Preppy Plaid Windowpane Check Y2K

$19.99

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Vtg 100% Linen Blazer Retro Preppy Academia Old Money Office Cottage Plaid
Vtg 100% Linen Blazer Retro Preppy Academia Old Money Office Cottage Plaid

$36.88

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Old Navy Women's Black Watch Plaid Peacoat Size L Old Money Ivy League Preppy
Old Navy Women's Black Watch Plaid Peacoat Size L Old Money Ivy League Preppy

$26.55

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Vintage Handknit boys fisherman sweater preppy ivy old money
Vintage Handknit boys fisherman sweater preppy ivy old money

$12.00

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Navy Blue Tweed Blazer L /XL Cotton Liz Clairborne Old Money Preppy
Navy Blue Tweed Blazer L /XL Cotton Liz Clairborne Old Money Preppy

$13.60

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Lands End Sweater Womens Medium Tennis Preppy Old Money Cable Knit Pickleball
Lands End Sweater Womens Medium Tennis Preppy Old Money Cable Knit Pickleball

$29.99

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Old Navy Gray Charcoal Pants Preppy Black Plaid Straight Classic Zip Men Size 34
Old Navy Gray Charcoal Pants Preppy Black Plaid Straight Classic Zip Men Size 34

$14.00

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Old Navy Blue Dress Midi Stretch Preppy White Polka Dot Classic Womens Size L
Old Navy Blue Dress Midi Stretch Preppy White Polka Dot Classic Womens Size L

$9.00

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NOS Old Navy Mini Skirt Preppy Size 6 Waist 30" NWT
NOS Old Navy Mini Skirt Preppy Size 6 Waist 30" NWT

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Jones NY 6 100% wool blazer Old Money Minimalist y2k cottage core preppy Career
Jones NY 6 100% wool blazer Old Money Minimalist y2k cottage core preppy Career

$26.00

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Lauren Ralph Lauren Pea Coat Women Medium Crest Double Breasted Old Money Preppy
Lauren Ralph Lauren Pea Coat Women Medium Crest Double Breasted Old Money Preppy

$112.48

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Old Navy Jacket Women's Extra Small Black Hooded Outdoors Preppy Normcore
Old Navy Jacket Women's Extra Small Black Hooded Outdoors Preppy Normcore

$12.00

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Old Navy XXL Dress Floral Paisley Preppy Romantic Artsy Cottagecore
Old Navy XXL Dress Floral Paisley Preppy Romantic Artsy Cottagecore

$19.98

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Old Navy Women XS Shaker-Stitch Cardigan Mustard Yellow Y2K Cottage Core Preppy
Old Navy Women XS Shaker-Stitch Cardigan Mustard Yellow Y2K Cottage Core Preppy

$21.99

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Y2K 2000s Old Navy Henley Top Women Green Cute Preppy Long Sleeve Sz M
Y2K 2000s Old Navy Henley Top Women Green Cute Preppy Long Sleeve Sz M

$15.00

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Northern Isles Cardigan Sweater Womens XL Blue Plaid Hand Embroidered Old Preppy
Northern Isles Cardigan Sweater Womens XL Blue Plaid Hand Embroidered Old Preppy

$24.95

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Ralph Lauren Purple Label Vintage Wool Suit Set Preppy Old Money Preppy Classic
Ralph Lauren Purple Label Vintage Wool Suit Set Preppy Old Money Preppy Classic

$150.00

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J. Crew Jacket Womens 6 Parke Tan Linen Blend Blazer Preppy Office Old Money
J. Crew Jacket Womens 6 Parke Tan Linen Blend Blazer Preppy Office Old Money

$44.88

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Vintage Shetland Wool UNISEX Sweater Soft Warm Preppy Old Money Quiet Luxury -L
Vintage Shetland Wool UNISEX Sweater Soft Warm Preppy Old Money Quiet Luxury -L

$17.88

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Old Navy Womens Top Medium Pink Striped Casual Cotton Preppy Button Front Shirt
Old Navy Womens Top Medium Pink Striped Casual Cotton Preppy Button Front Shirt

$9.99

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Talbots Womens Aberdeen Blazer Petite Size 14P Blue Career Old Money Preppy
Talbots Womens Aberdeen Blazer Petite Size 14P Blue Career Old Money Preppy

$35.88

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Old Navy Top M Mustard Eyelet Boho Cottagecore Peasant Preppy Coastal Linen Blnd
Old Navy Top M Mustard Eyelet Boho Cottagecore Peasant Preppy Coastal Linen Blnd

$11.98

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VTG Blue Cropped Cardigan Chunky Gold Button Preppy Old Money Nautical Sweater
VTG Blue Cropped Cardigan Chunky Gold Button Preppy Old Money Nautical Sweater

$17.99

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Lauren Ralph Lauren Combed Cotton Blazer in Black Sz Large, Old Money Preppy
Lauren Ralph Lauren Combed Cotton Blazer in Black Sz Large, Old Money Preppy

$80.00

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Old Navy Button Down Shirt Men's Size XXL Blue White Striped Vintage Fit Preppy
Old Navy Button Down Shirt Men's Size XXL Blue White Striped Vintage Fit Preppy

$19.99

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VTG Tommy Hilfiger Sweater Womens XL Cable Knit V-Neck Tennis Preppy Old Money
VTG Tommy Hilfiger Sweater Womens XL Cable Knit V-Neck Tennis Preppy Old Money

$34.95

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Old Navy The Boyfriend Button Down Top Size Medium Red Plaid Flannel Preppy
Old Navy The Boyfriend Button Down Top Size Medium Red Plaid Flannel Preppy

$16.19

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Chicos Womens Multi Color Tweed Jacket Size XL 3 Rainbow Old Money Preppy
Chicos Womens Multi Color Tweed Jacket Size XL 3 Rainbow Old Money Preppy

$28.88

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Gap Plaid Mini Skirt Womens 8 Pink Wool Blend Academia Old Money Preppy Coquette
Gap Plaid Mini Skirt Womens 8 Pink Wool Blend Academia Old Money Preppy Coquette

$14.95

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Old Navy Short Adult 40 Blue White Chino Floral Outdoors Preppy Casual Mens
Old Navy Short Adult 40 Blue White Chino Floral Outdoors Preppy Casual Mens

$3.24

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Old Navy Dress L Yellow Gingham Seersucker Babydoll Puff Milkmaid Cottagecore
Old Navy Dress L Yellow Gingham Seersucker Babydoll Puff Milkmaid Cottagecore

$19.98

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Old Navy Dress Womens M Green Linen Blend Sleeveless Button Front Pockets Preppy
Old Navy Dress Womens M Green Linen Blend Sleeveless Button Front Pockets Preppy

$13.29

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Old School Clothing Co. Shirt Adult Large Blue White Plaid Preppy Casual Mens
Old School Clothing Co. Shirt Adult Large Blue White Plaid Preppy Casual Mens

$14.14

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Ralph Lauren Layered Sweater Twofer Women XL Grey Preppy Old Money
Ralph Lauren Layered Sweater Twofer Women XL Grey Preppy Old Money

$24.95

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VTG Y2K 90s Old Navy Blue Striped Rugby Long Sleeve Polo Shirt Preppy XXL
VTG Y2K 90s Old Navy Blue Striped Rugby Long Sleeve Polo Shirt Preppy XXL

$22.50

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Old Navy Blazer Womens XXL Brown Plaid Taylor Relaxed Suit Jacket Preppy NWT
Old Navy Blazer Womens XXL Brown Plaid Taylor Relaxed Suit Jacket Preppy NWT

$25.98

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Old Navy Girls Sz M 8 Blouse Shirt Red Geometric Print 3/4 Sleeve Preppy V-Neck
Old Navy Girls Sz M 8 Blouse Shirt Red Geometric Print 3/4 Sleeve Preppy V-Neck

$4.25

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Oversized Academia Vest Top Small Old Money Fall Office Siren Preppy Clean Girl
Oversized Academia Vest Top Small Old Money Fall Office Siren Preppy Clean Girl

$17.97

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Old Navy Rugby Shirt Men XL Beige Navy Long Sleeve Preppy Outdoors Heavy Cotton
Old Navy Rugby Shirt Men XL Beige Navy Long Sleeve Preppy Outdoors Heavy Cotton

$20.23

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Ann Taylor Plaid Pencil Skirt Button Details Size 4 Acadamia Old Money Preppy
Ann Taylor Plaid Pencil Skirt Button Details Size 4 Acadamia Old Money Preppy

$14.50

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J.Crew Emilie Sweater Women’s XS Lady Jacket Cream Gold Buttons Old Money Preppy
J.Crew Emilie Sweater Women’s XS Lady Jacket Cream Gold Buttons Old Money Preppy

$46.50

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Womens Checked Shorts Size 16 Navy Blue Gingham Preppy Academia Old Navy NWT XL
Womens Checked Shorts Size 16 Navy Blue Gingham Preppy Academia Old Navy NWT XL

$17.00

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VINTAGE Old Navy Green Pullover Sweater Size Large Mens Casual Preppy Y2K
VINTAGE Old Navy Green Pullover Sweater Size Large Mens Casual Preppy Y2K

$19.00

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VTG 10 Old Money Preppy Safari British Khaki 100% Cotton Tan Maxi Wrap Skirt
VTG 10 Old Money Preppy Safari British Khaki 100% Cotton Tan Maxi Wrap Skirt

$17.00

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Ralph Lauren Paisley Blouse L Black White Shirt Old Money Capsule Preppy Classic
Ralph Lauren Paisley Blouse L Black White Shirt Old Money Capsule Preppy Classic

$33.97

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Old Navy Shirt Womens Small Green Button Up Tencel Preppy Casual Outdoors Ladies
Old Navy Shirt Womens Small Green Button Up Tencel Preppy Casual Outdoors Ladies

$14.14

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Old Navy Textured Houndstooth Plaid Blazer Womens Sz M Timeless Preppy City Law
Old Navy Textured Houndstooth Plaid Blazer Womens Sz M Timeless Preppy City Law

$19.99

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Ralph Lauren Wool Blend Longer length Coat Sz 16 Gray Classic Old Money Preppy
Ralph Lauren Wool Blend Longer length Coat Sz 16 Gray Classic Old Money Preppy

$59.97

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Old Navy The Classic Fit Oxford Shirt Men's Medium Slim Fit Striped Preppy Geek
Old Navy The Classic Fit Oxford Shirt Men's Medium Slim Fit Striped Preppy Geek

$16.99

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Preppy Double Breasted Trending White Cropped Trench Coat Old Navy Size Large
Preppy Double Breasted Trending White Cropped Trench Coat Old Navy Size Large

$30.40

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Old Navy Top Womens 2XL Blue White Stripe Button Up Pocket Designer Preppy
Old Navy Top Womens 2XL Blue White Stripe Button Up Pocket Designer Preppy

$14.42

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Old Navy Mini Skirt Tartan Plaid Wool Blend Preppy Grunge Academia Indie Size 0
Old Navy Mini Skirt Tartan Plaid Wool Blend Preppy Grunge Academia Indie Size 0

$14.99

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Lauren Ralph Lauren Womens Cable Knit Sweater Size Large White Old Money Preppy
Lauren Ralph Lauren Womens Cable Knit Sweater Size Large White Old Money Preppy

$23.88

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Old Navy Blouse Women's XS Pink Button Down Long Sleeve Collared Preppy
Old Navy Blouse Women's XS Pink Button Down Long Sleeve Collared Preppy

$5.59

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Old Navy Jeans Mens 36x36 Blue Denim Straight Leg Classiccore Preppy Casual
Old Navy Jeans Mens 36x36 Blue Denim Straight Leg Classiccore Preppy Casual

$18.22

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Old Navy Men's Crew Neck Pullover Chunky Knit Sweater Tan Brown Preppy Large
Old Navy Men's Crew Neck Pullover Chunky Knit Sweater Tan Brown Preppy Large

$9.00

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Old Navy Blazer Jacket XXL / 2X Linen Navy Blue Nautical Oversized Preppy Lagen
Old Navy Blazer Jacket XXL / 2X Linen Navy Blue Nautical Oversized Preppy Lagen

$24.30

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Preppy Western Old Money Classic Chic Navy Silk Long Skirt 8 Lauren Ralph Lauren
Preppy Western Old Money Classic Chic Navy Silk Long Skirt 8 Lauren Ralph Lauren

$59.99

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Old Navy Boys Sz 2T Flannel Plaid Button Up Shirt 100% Cotton Preppy
Old Navy Boys Sz 2T Flannel Plaid Button Up Shirt 100% Cotton Preppy

$7.65

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Old Navy "Preppy Bison" all over print button down Youth Large (10-12)
Old Navy "Preppy Bison" all over print button down Youth Large (10-12)

$8.88

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COS Khaki Slacks Pants Preppy Academia Work Office Old Money Wardrobe Staple 30R
COS Khaki Slacks Pants Preppy Academia Work Office Old Money Wardrobe Staple 30R

$18.88

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Old Navy Coat Womens Medium Green Button Front Classiccore Preppy Jacket
Old Navy Coat Womens Medium Green Button Front Classiccore Preppy Jacket

$22.50

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Old Navy Sweaters Womens 2X Plus Fisherman cable Knit Long Sleeve Casual Preppy
Old Navy Sweaters Womens 2X Plus Fisherman cable Knit Long Sleeve Casual Preppy

$16.39

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Old Navy Men 30x30 Pants Cream Chino Tapere Button Fly 100% Linen Coastal Preppy
Old Navy Men 30x30 Pants Cream Chino Tapere Button Fly 100% Linen Coastal Preppy

$17.64

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60s Knee Length Mini Midi Skirt Brown Preppy Old Money VTG 1960s
60s Knee Length Mini Midi Skirt Brown Preppy Old Money VTG 1960s

$13.92

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Old Navy Sweater Mens Large Blue Striped Crew Neck Preppy Classiccore Sailor
Old Navy Sweater Mens Large Blue Striped Crew Neck Preppy Classiccore Sailor

$13.11

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Old Navy Linen Blend Button Up Shirt Large Tan Khaki Long Sleeve Preppy Mens
Old Navy Linen Blend Button Up Shirt Large Tan Khaki Long Sleeve Preppy Mens

$18.03

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60s Velvet Bow Vintage Maxi Shift Evening Cocktail Party Dress Old Money Preppy
60s Velvet Bow Vintage Maxi Shift Evening Cocktail Party Dress Old Money Preppy

$35.00

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Old Navy Butter Yellow Knit Preppy Casual Bright Pullover Sweater Women's Size S
Old Navy Butter Yellow Knit Preppy Casual Bright Pullover Sweater Women's Size S

$12.00

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Vintage 90s Polo Ralph Lauren Shirts Mens 36 Plaid Pleated Preppy Old Money USA
Vintage 90s Polo Ralph Lauren Shirts Mens 36 Plaid Pleated Preppy Old Money USA

$27.48

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Vintage Sweater Mens XL Beige V Neck Ribbed Collar Preppy Minimalist Old Money
Vintage Sweater Mens XL Beige V Neck Ribbed Collar Preppy Minimalist Old Money

$29.95

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