1950s-dress-up-boys

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1950's Wool Zip up Front Marching Nutcracker Cardigan Sweater Boys
1950's Wool Zip up Front Marching Nutcracker Cardigan Sweater Boys

$39.99

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Kids Childen Boy Playing Fashion Dressed Up Black & White Vtg 1950's Photo
Kids Childen Boy Playing Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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Cowboy Dress Up Boots Boy Kid Wearing Black & White Vtg 1950's Photo
Cowboy Dress Up Boots Boy Kid Wearing Black & White Vtg 1950's Photo

$4.95

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Happy Boy Child Playing Fashion Dressed Up Black & White Vtg 1950's Photo
Happy Boy Child Playing Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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Kids Girls Boys Dress Up American Flags 35mm Slide 1950s Red Border Kodachrome
Kids Girls Boys Dress Up American Flags 35mm Slide 1950s Red Border Kodachrome

$12.99

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Kids Girls Boys Dress Up 35mm Slide 1950s Red Border Kodachrome
Kids Girls Boys Dress Up 35mm Slide 1950s Red Border Kodachrome

$12.99

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1950s Class Photo School Age Children Boys and Girls Dressed Up Retro MCM Formal
1950s Class Photo School Age Children Boys and Girls Dressed Up Retro MCM Formal

$10.49

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1950's Boy Dressed up Figurine Planter
1950's Boy Dressed up Figurine Planter

$16.00

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Kids Childen Boy Playing Couch Fashion Dressed Up Black & White Vtg 1950's Photo
Kids Childen Boy Playing Couch Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo
Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo

$4.95

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Kids Childen Boy Fashion Dressed Up Black & White Vtg 1950's Photo
Kids Childen Boy Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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Kids Childen Boy Playing Fashion Dressed Up Black & White Vtg 1950's Photo
Kids Childen Boy Playing Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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Vintage 1950’s Quaker Oats Palefaces Pow Wow Pouch Indian Kids Dress Up Kit
Vintage 1950’s Quaker Oats Palefaces Pow Wow Pouch Indian Kids Dress Up Kit

$25.00

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Freeman Rare Wingtip Shoes Sz 9.5 B Mens Leather Black Yellow Dress 47363
Freeman Rare Wingtip Shoes Sz 9.5 B Mens Leather Black Yellow Dress 47363

$199.95

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1950s Girls Poodle Skirt Dress up Kit, Bobby Sock,Chiffon Scarf, 50s Costume ...
1950s Girls Poodle Skirt Dress up Kit, Bobby Sock,Chiffon Scarf, 50s Costume ...

$38.32

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1950s Girls Poodle Skirt Dress up Kit, Bobby Sock,Chiffon Scarf, 50s Costume ...
1950s Girls Poodle Skirt Dress up Kit, Bobby Sock,Chiffon Scarf, 50s Costume ...

$37.65

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VTG 1950s Young Boy In Sailor Costume Photo 3x2 Black White Dress-Up Lawn Smilin
VTG 1950s Young Boy In Sailor Costume Photo 3x2 Black White Dress-Up Lawn Smilin

$3.49

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Bike Bicycle Kids Childen Boy Fashion Dressed Up Black & White Vtg 1950's Photo
Bike Bicycle Kids Childen Boy Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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CarSpotter: 1950s Ford w Mom & Son All Dressed Up; 1962: Vintage SNAPSHOT Photo
CarSpotter: 1950s Ford w Mom & Son All Dressed Up; 1962: Vintage SNAPSHOT Photo

$5.98

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Boys Size 12 Dress Shoes - 1950s 60s Child's Lace Up Oxfords Black Leather NIB
Boys Size 12 Dress Shoes - 1950s 60s Child's Lace Up Oxfords Black Leather NIB

$59.99

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REAR 1950"s Toddler Boys Black & White Oxford Dress Shoe size see measurement
REAR 1950"s Toddler Boys Black & White Oxford Dress Shoe size see measurement

$20.00

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1950s Cute Boy Dress up Private School Suit Hollywood Los Angeles 8x10
1950s Cute Boy Dress up Private School Suit Hollywood Los Angeles 8x10

$14.84

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Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo
Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo

$4.95

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Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo
Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo

$4.95

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35MM Found Photo Slide Kodachrome Red Border Boys Dressed Up Attitude 1950s
35MM Found Photo Slide Kodachrome Red Border Boys Dressed Up Attitude 1950s

$8.00

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Bikes Bicycle Kids Childen Boy Fashion Dressed Up Black & White Vtg 1950's Photo
Bikes Bicycle Kids Childen Boy Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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Happy Baby Child Playing Fashion Dressed Up Black & White Vtg 1950's Photo
Happy Baby Child Playing Fashion Dressed Up Black & White Vtg 1950's Photo

$4.95

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1950 s Vintage Photo young child Boy all dressed up Sailor Uniform front porch
1950 s Vintage Photo young child Boy all dressed up Sailor Uniform front porch

$5.49

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Framed Children Breaking Out Photo 1950s Dressed Up Kids Portrait Snapshot A3689
Framed Children Breaking Out Photo 1950s Dressed Up Kids Portrait Snapshot A3689

$29.95

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1950s Girls Poodle Skirt Dress up Kit, Bobby Sock,Chiffon Scarf, 50s Costume ...
1950s Girls Poodle Skirt Dress up Kit, Bobby Sock,Chiffon Scarf, 50s Costume ...

$38.32

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Vtg 1950s Young Baby Boy Dressed Up Outside B&W Portrait Photo Photograph
Vtg 1950s Young Baby Boy Dressed Up Outside B&W Portrait Photo Photograph

$23.10

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Man's Oxfords Calvin Klein Brodie Oxford
Man's Oxfords Calvin Klein Brodie Oxford

$129.99

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Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo
Fashion Dressed Up Kids Childen Boy Girl Black & White Vtg 1950's Photo

$4.95

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1950s Dad With boys Dressed up Vintage Snapshot Photo Los Angeles
1950s Dad With boys Dressed up Vintage Snapshot Photo Los Angeles

$12.47

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4pc Vintage 1930's -1950’s Photos Family Lady Nurse Boys Dressed Up
4pc Vintage 1930's -1950’s Photos Family Lady Nurse Boys Dressed Up

$14.99

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Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy Family Retro Tv 1950s
Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy Family Retro Tv 1950s

$11.00

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Vintage 1950's Photograph Boy Dressed Up as Cowboy with Cute Baby in the Park
Vintage 1950's Photograph Boy Dressed Up as Cowboy with Cute Baby in the Park

$19.97

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Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy 1950s
Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy 1950s

$11.00

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Boy's Grease T-Birds Infant Costume 6-9 Months
Boy's Grease T-Birds Infant Costume 6-9 Months

$15.00

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2 Vintage 1950's Photos of Boy Girl Nice Prom Dress Before & After Dance 💃
2 Vintage 1950's Photos of Boy Girl Nice Prom Dress Before & After Dance 💃

$9.90

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Kid Little Boy & Grandma Play Dress-Up Vintage 1950s Photo
Kid Little Boy & Grandma Play Dress-Up Vintage 1950s Photo

$10.99

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Boys Dress Shoes - Size 8.5 1950s 60s Child's Lace Up Oxfords - Authentic NIB
Boys Dress Shoes - Size 8.5 1950s 60s Child's Lace Up Oxfords - Authentic NIB

$59.99

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Vintage Santa Christmas Magnetic Dress Up Santa On Vacation Outfits 22 Pieces
Vintage Santa Christmas Magnetic Dress Up Santa On Vacation Outfits 22 Pieces

$24.99

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1950s (?) Photo - Cute Little Boy Dressed Up in a Cowboy Costume Halloween?
1950s (?) Photo - Cute Little Boy Dressed Up in a Cowboy Costume Halloween?

$9.98

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1950s BOY INDIAN COSTUME PLAINSMAN BY BLUE JEAN CORP. SIZE 5, UNWORN
1950s BOY INDIAN COSTUME PLAINSMAN BY BLUE JEAN CORP. SIZE 5, UNWORN

$60.00

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Class Nerd 50's Retro Plaid Sock Hop Prom Fancy Dress Up Halloween Child Costume
Class Nerd 50's Retro Plaid Sock Hop Prom Fancy Dress Up Halloween Child Costume

$34.85

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Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy Play Doctor 1950s
Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy Play Doctor 1950s

$11.00

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Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy Mom Guitar 1950s
Vintage Found Photo Christmas Day Boy Dressed Up As Cowboy Mom Guitar 1950s

$11.00

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Vintage 1950s Color Photo BOY DRESSED UP IN HIS BEST SUIT SITTING ON BLUE CHAIR
Vintage 1950s Color Photo BOY DRESSED UP IN HIS BEST SUIT SITTING ON BLUE CHAIR

$6.99

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1950s Native American Indian Western Halloween costume 2pc Vintage Boys Size-6
1950s Native American Indian Western Halloween costume 2pc Vintage Boys Size-6

$59.99

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Boy’s Sweater 1950’s Novelty Zip up Front Dog & Doghouse Cardigan XS
Boy’s Sweater 1950’s Novelty Zip up Front Dog & Doghouse Cardigan XS

$40.50

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1950s Young Teen Boy Dressed Up Bow Cute Vintage Photo
1950s Young Teen Boy Dressed Up Bow Cute Vintage Photo

$19.99

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1950's Colorized - Very Odd - Two Boys Dressed in Girls Outfits w/ A Baby Photo
1950's Colorized - Very Odd - Two Boys Dressed in Girls Outfits w/ A Baby Photo

$19.88

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Photo Merry Christmas Card "hi there" Dressed Up Happy Boy & Girl Names 1950s ?
Photo Merry Christmas Card "hi there" Dressed Up Happy Boy & Girl Names 1950s ?

$4.88

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Vintage 1950s Color Photo of Boy & Pretty Teenage Girl In Prom Dress Ball Gown
Vintage 1950s Color Photo of Boy & Pretty Teenage Girl In Prom Dress Ball Gown

$9.90

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3193 Butterick Vintage SEWING Pattern Toddler Girls Boys Costumes Halloween Bear
3193 Butterick Vintage SEWING Pattern Toddler Girls Boys Costumes Halloween Bear

$5.59

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Girl Boy Dressed Up Bow Tie Umbrella 1950s 35mm Slide Red Border Kodachrome
Girl Boy Dressed Up Bow Tie Umbrella 1950s 35mm Slide Red Border Kodachrome

$17.99

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1950s Boy & Girl Dressed Up Like Their Parents - Vintage Red Border 35mm Slide
1950s Boy & Girl Dressed Up Like Their Parents - Vintage Red Border 35mm Slide

$12.45

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1950 s Vintage Photo young children Fancy Party Invite all dressed up 1954
1950 s Vintage Photo young children Fancy Party Invite all dressed up 1954

$5.49

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Vintage snapshot boy indian costume tomahawk headdress feathers dress up
Vintage snapshot boy indian costume tomahawk headdress feathers dress up

$4.99

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Vintage Photo 1950s Children Party Mid Century Fancy Dresses Toddler Baby 1958
Vintage Photo 1950s Children Party Mid Century Fancy Dresses Toddler Baby 1958

$9.95

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Christmas Ornament Boy in Indian Costume 1950s Style Barefoot Headdress Arrows
Christmas Ornament Boy in Indian Costume 1950s Style Barefoot Headdress Arrows

$16.00

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Merry Christmas Big Boy Card , Dressed up Panda Bear 1950's
Merry Christmas Big Boy Card , Dressed up Panda Bear 1950's

$1.99

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Vintage Children's Clothing New Old Stock Little Boys Blazer & Shirt w/Bow Tie
Vintage Children's Clothing New Old Stock Little Boys Blazer & Shirt w/Bow Tie

$19.99

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Vintage Snapshot Photo Two Cute Boys Kids Dressed Up with Pony Horse Saddle
Vintage Snapshot Photo Two Cute Boys Kids Dressed Up with Pony Horse Saddle

$12.00

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VTG 1950s Color Photo PRETTY MUM ADORABLE YOUNG BOY & GIRL DRESSED FOR EASTER
VTG 1950s Color Photo PRETTY MUM ADORABLE YOUNG BOY & GIRL DRESSED FOR EASTER

$6.99

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Boy Dressed Up Father Navy Uniform 1950s Slide Red Border Kodachrome Americana
Boy Dressed Up Father Navy Uniform 1950s Slide Red Border Kodachrome Americana

$14.99

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Simplicity 1769 Girls Boys Cape Costumes Sewing Pattern Sz 3-8
Simplicity 1769 Girls Boys Cape Costumes Sewing Pattern Sz 3-8

$3.99

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5 Vintage 1950s High School Dance Girl Boy Gown Dress B & W Photos Photographs
5 Vintage 1950s High School Dance Girl Boy Gown Dress B & W Photos Photographs

$8.46

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1959 Press Photo Cute 1950s Boys Dressed as Aviators at Airport South Florida
1959 Press Photo Cute 1950s Boys Dressed as Aviators at Airport South Florida

$23.99

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Grease T-Birds Infant Costume 6-9 Months Preowned
Grease T-Birds Infant Costume 6-9 Months Preowned

$24.95

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Vintage 1950's PETER PAN Walt Disney Costume Pattern Advance 709 Complete
Vintage 1950's PETER PAN Walt Disney Costume Pattern Advance 709 Complete

$12.35

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VINTAGE 5X7” B&W PHOTO Soldier With Little boy Dressed Like A Soldier 1950’s
VINTAGE 5X7” B&W PHOTO Soldier With Little boy Dressed Like A Soldier 1950’s

$9.00

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VINTAGE 1957 GEO Z LEFTON BOY FIGURINE 050 Playing Dress Up Helmet D7
VINTAGE 1957 GEO Z LEFTON BOY FIGURINE 050 Playing Dress Up Helmet D7

$14.95

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5 Vintage 1950s High School Dance Girl Boy Gown Dress B & W Photo Photograph
5 Vintage 1950s High School Dance Girl Boy Gown Dress B & W Photo Photograph

$8.49

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1950's Vintage Carlson Dolls Sleepy Eye Boy W/Bow Tag +3 Native American Dolls
1950's Vintage Carlson Dolls Sleepy Eye Boy W/Bow Tag +3 Native American Dolls

$18.80

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Vintage Boy Figurines Playing Dress-up Glossy Ceramic Porcelain Winking 3"
Vintage Boy Figurines Playing Dress-up Glossy Ceramic Porcelain Winking 3"

$50.28

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Big Boys Alfi Oxfords- Cat&Jack Black
Big Boys Alfi Oxfords- Cat&Jack Black

$18.74

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Big Boys Alfi Oxfords- Cat & Jack Black Size 2
Big Boys Alfi Oxfords- Cat & Jack Black Size 2

$19.49

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OLD VINTAGE PHOTO PRETTY LITTLE GIRL IN SPANISH DRESS WITH FAN 1950's
OLD VINTAGE PHOTO PRETTY LITTLE GIRL IN SPANISH DRESS WITH FAN 1950's

$16.99

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🐻 Big Boys Alfi Oxfords- Cat & Jack Black Size 4
🐻 Big Boys Alfi Oxfords- Cat & Jack Black Size 4

$21.99

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Well Dressed Couple Gloves Purse 1950’s Photograph Picture Black & White
Well Dressed Couple Gloves Purse 1950’s Photograph Picture Black & White

$12.41

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Vintage 1940's-1950's Photo of a Boy Dressed Up as a Cowboy with Wagon
Vintage 1940's-1950's Photo of a Boy Dressed Up as a Cowboy with Wagon

$5.00

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Lot of 2 Vintage 1950s Photos FINE LOOKING DRESSED UP FAMILY DAD MOM CUTE BOY
Lot of 2 Vintage 1950s Photos FINE LOOKING DRESSED UP FAMILY DAD MOM CUTE BOY

$7.99

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Khaki Shirt for Boys -1950'S Vintage Small Coneset brand new never worn
Khaki Shirt for Boys -1950'S Vintage Small Coneset brand new never worn

$15.00

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1940s Photo Adorable Alter Boys full dress Church 5x7 original
1940s Photo Adorable Alter Boys full dress Church 5x7 original

$4.00

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Butterick 6248 Penguin, Cat, Monkey & Caped Devil Sz 34" Chest COSTUME PATTERN
Butterick 6248 Penguin, Cat, Monkey & Caped Devil Sz 34" Chest COSTUME PATTERN

$24.95

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1950s Butterick 6246 Men Costume Pattern Santa, Doctor, Painter Chest: 30 Uncut
1950s Butterick 6246 Men Costume Pattern Santa, Doctor, Painter Chest: 30 Uncut

$38.65

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🐻 Big Boys Alfi Oxfords- Cat&Jack Black Size 13
🐻 Big Boys Alfi Oxfords- Cat&Jack Black Size 13

$21.99

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Lot of 16 Vintage 1940-50's B&W Dress Up Little Cowboys Original Snapshots Dogs
Lot of 16 Vintage 1940-50's B&W Dress Up Little Cowboys Original Snapshots Dogs

$44.99

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Boys Adidas Jumper Track Bomber Jacket Fleece Lining Snaps / Zip Up
Boys Adidas Jumper Track Bomber Jacket Fleece Lining Snaps / Zip Up

$34.99

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🐻 Big Boys Alfi Oxfords- Cat&Jack Black Size 1
🐻 Big Boys Alfi Oxfords- Cat&Jack Black Size 1

$21.99

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1950s Pretty Young Girl Pigtails Long Hair Dress USSR Vintage Photo Portrait
1950s Pretty Young Girl Pigtails Long Hair Dress USSR Vintage Photo Portrait

$5.99

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Vintage Trimfoot Co. New White/beige Size 9 Lace Up Boy Dress Shoes
Vintage Trimfoot Co. New White/beige Size 9 Lace Up Boy Dress Shoes

$32.97

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Vtg 1956 McCall's #2115 Pattern Boy's Sz 4 Pirate, Turk, Genie, Bullfighter
Vtg 1956 McCall's #2115 Pattern Boy's Sz 4 Pirate, Turk, Genie, Bullfighter

$9.99

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McCall's 5439 "1950's Style" Poodle Skirt & Top Pattern Sz 7-8-10 UC
McCall's 5439 "1950's Style" Poodle Skirt & Top Pattern Sz 7-8-10 UC

$3.99

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vintage made 1950s hong kong 13in doll with handcrafted crochet suit and tie.
vintage made 1950s hong kong 13in doll with handcrafted crochet suit and tie.

$16.44

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Vtg 1950s Proud Dressed Up Sitting Smiling Baby Boy B&W Portrait Photo Postcard
Vtg 1950s Proud Dressed Up Sitting Smiling Baby Boy B&W Portrait Photo Postcard

$25.10

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Chiffon A Line Lace Decorated Mother Of The Bride Groom Dress With Ruffles Dress
Chiffon A Line Lace Decorated Mother Of The Bride Groom Dress With Ruffles Dress

$153.43

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Smart Fit Boys Exotic Oxford Black Size 11.5 youth
Smart Fit Boys Exotic Oxford Black Size 11.5 youth

$19.99

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