Toddler Boys' Button Up Shirts

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Toddler Boys' Button Up Shirts

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Boys Embroidered Beach Button Up Shirt - Amalfi Coast - view 1
Sale Price: $37.17Original Price: $61.9540% OFF

$27.88 WITH CODE PLACE25

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Boys Embroidered Tropical Leaf Linen-Blend Button Up Shirt - Amalfi Coast - view 1
Sale Price: $37.17Original Price: $61.9540% OFF

$27.88 WITH CODE PLACE25

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Boys Embroidered Tropical Leaf Gauze Button Up Shirt - Amalfi Coast - view 1
Sale Price: $37.17Original Price: $61.9540% OFF

$27.88 WITH CODE PLACE25

Boys Embroidered Tropical Leaf Linen-Blend Button Up Shirt - Amalfi Coast - view 1
Sale Price: $37.17Original Price: $61.9540% OFF

$27.88 WITH CODE PLACE25

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Boys Plaid Button Up Shirt - Coastal Cutie - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Boys Plaid Poplin Button Up Shirt - Dino Friends - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon3 reviews

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Boys Textured Button Up Shirt - Driftwood Bay - view 1
Sale Price: $30.98Original Price: $61.9550% OFF

$23.23 WITH CODE PLACE25

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Boys Schiffli Bunny Poplin Button Up Shirt - Blue Belle - view 1
Sale Price: $13.24Original Price: $52.9575% OFF
Star Rating Icon3 reviews

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Boys Schiffli Truck Oxford Button Up Shirt - Dino Friends - view 1
Sale Price: $14.24Original Price: $56.9575% OFF
Star Rating Icon13 reviews

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Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
Sale Price: $30.98Original Price: $61.9550% OFF

$23.23 WITH CODE PLACE25

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Boys Plaid Poplin Button Up Shirt - Little Snowflake - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon4 reviews

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Boys Reindeer Corduroy Button Up Shirt - Holiday Express - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon7 reviews

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Mens Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon3 reviews

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Boys Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $19.98Original Price: $49.9560% OFF

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Boys Plaid Poplin Button Up Shirt - Campus Cuties - view 1
Sale Price: $12.88Original Price: $42.9570% OFF
Star Rating Icon1 reviews

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Mens Dad And Me Plaid Poplin Button Up Shirt - Lavender Fields - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon6 reviews

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Boys Plaid Flannel Button Up Shirt - Holiday Express - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon8 reviews

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Boys Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Mens Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $28.78Original Price: $71.9560% OFF

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Boys Dad And Me Plaid Poplin Button Up Shirt - Lavender Fields - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon3 reviews

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Boys Schiffli Reindeer Oxford Button Up Shirt - Holiday Express - view 1
Sale Price: $14.24Original Price: $56.9575% OFF
Star Rating Icon8 reviews

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Mens Dad And Me Gingham Colorblock Poplin Button Up Shirt - Garden Party - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon8 reviews

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Boys Railroad Striped Seersucker Button Up Shirt - Enchanted Garden - view 1
Sale Price: $23.18Original Price: $57.9560% OFF
Star Rating Icon2 reviews

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Boys Dino Button Up Shirt - Little Essentials - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon5 reviews

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Boys Gingham Seersucker Button Up Shirt - Enchanted Garden - view 1
Sale Price: $23.18Original Price: $57.9560% OFF
Star Rating Icon1 reviews

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Boys Plaid Luxe Cozy Knit Button Up Shirt - Highland Hills - view 1
Sale Price: $14.98Original Price: $49.9570% OFF
Star Rating Icon4 reviews

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Boys Plaid Madras Flannel Button Up Shirt - Holiday Express - view 1
Sale Price: $14.99Original Price: $59.9575% OFF
Star Rating Icon11 reviews

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Boys Lemon Poplin Button Up Shirt - Little Essentials - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Most Favorited

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Kids Dad And Me Striped Linen-Blend Button Up Shirt - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon13 reviews

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Boys Embroidered Lighthouse Denim Button Up Shirt - Driftwood Bay - view 1
Sale Price: $28.78Original Price: $71.9560% OFF
Star Rating Icon1 reviews

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Kids Plaid Button Up Shirt - Fall Celebrations - view 1
Sale Price: $13.48Original Price: $44.9570% OFF
Star Rating Icon3 reviews

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Boys Plaid Poplin Button Up Shirt - Garden Party - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon9 reviews

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Boys Schiffli Train Oxford Button Up Shirt - Little Snowflake - view 1
Sale Price: $14.24Original Price: $56.9575% OFF
Star Rating Icon16 reviews

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Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
Sale Price: $25.98Original Price: $64.9560% OFF
Star Rating Icon1 reviews

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Boys Embroidered Fox Corduroy Button Up Shirt - Highland Hills - view 1
Sale Price: $19.48Original Price: $64.9570% OFF
Star Rating Icon9 reviews

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Boys Plaid Poplin Button Down Shirt - Holiday Express - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon8 reviews

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Boys Embroidered Fish Button Up Shirt - Driftwood Bay - view 1
Sale Price: $28.78Original Price: $71.9560% OFF

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Boys Plaid Button Up Shirt - Highland Hills - view 1
Sale Price: $14.98Original Price: $49.9570% OFF
Star Rating Icon2 reviews

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Boys Schiffli Christmas Tree Corduroy Button Up Shirt - All Dressed Up - view 1
Sale Price: $14.24Original Price: $56.9575% OFF
Star Rating Icon7 reviews

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Kids Pinstripe Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $19.98Original Price: $49.9560% OFF

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Kids Linen-Blend Button Up Shirt - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon13 reviews

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Boys Embroidered Nutcracker Oxford Button Up Shirt - New York City Ballet by GYMBOREE - view 1
Sale Price: $30.38Original Price: $75.9560% OFF
Star Rating Icon1 reviews

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Boys Poplin Button Up Shirt - All Dressed Up - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Mens Matching Family Plaid Poplin Button Up Shirt - Spring Celebrations - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon6 reviews

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Boys Striped Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon2 reviews

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Boys Schiffli Snow Man Corduroy Button Up Shirt - Royal Christmas - view 1
Sale Price: $17.08Original Price: $56.9570% OFF
Star Rating Icon6 reviews

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Boys Flamingo Poplin Button Up Shirt - Seaside Palms - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Boys Matching Family Plaid Poplin Button Up Shirt - Spring Celebrations - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon5 reviews

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Boys Embroidered Santa Corduroy Button Up Shirt - Very Merry - view 1
Sale Price: $11.74Original Price: $46.9575% OFF
Star Rating Icon14 reviews

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Boys Striped Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon2 reviews

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Kids Linen-Blend Button Up Shirt - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon13 reviews

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Boys Gingham Flannel Button Up Shirt - First Frost - view 1
Sale Price: $22.78Original Price: $75.9570% OFF
Star Rating Icon5 reviews

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Boys Matching Family Plaid Poplin Button Up Shirt - Royal Christmas - view 1
Sale Price: $12.88Original Price: $42.9570% OFF
Star Rating Icon3 reviews

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Boys Schiffli Flamingo Button Up Shirt - Seaside Palms - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon9 reviews

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Boys Colorblock Oxford Button Up Shirt - Spring Celebrations - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon15 reviews

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Boys Dad And Me Plaid Button Up Shirt - Nutcracker - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon3 reviews

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Boys Quilted Scuba Button Up Shirt - First Frost - view 1
Sale Price: $24.58Original Price: $81.9570% OFF
Star Rating Icon4 reviews

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Mens Matching Family Plaid Poplin Button Up Shirt - Royal Christmas - view 1
Sale Price: $19.48Original Price: $64.9570% OFF
Star Rating Icon4 reviews

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Mens Matching Family Plaid Poplin Button Up Shirt - A Royal Christmas - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon8 reviews

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Mens Matching Family Tropical Button Up Shirt - Splish-Splash - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon3 reviews

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Boys Dad And Me Plaid Poplin Button Up Shirt - Lovely Lavender - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon6 reviews

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Kids Linen-Blend Button Up Shirt - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon14 reviews

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Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $23.18Original Price: $57.9560% OFF
Star Rating Icon7 reviews

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Boys Plaid Flannel Button Up Shirt - Royal Christmas - view 1
Sale Price: $17.38Original Price: $57.9570% OFF
Star Rating Icon14 reviews

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Mens Matching Family Plaid Poplin Button Up Shirt - All Dressed Up - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon6 reviews

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Mens Dad And Me Plaid Poplin Button Up Shirt - Lovely Lavender - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon3 reviews

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Boys Tropical Button Up Shirt - Splish-Splash - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon7 reviews

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Boys Pinstripe Bunny Poplin Button Up Shirt - Spring Celebrations - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon3 reviews

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Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $23.18Original Price: $57.9560% OFF
Star Rating Icon7 reviews

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Boys Plaid Colorblock Flannel Button Up Shirt - Royal Christmas - view 1
Sale Price: $24.58Original Price: $81.9570% OFF
Star Rating Icon4 reviews

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Boys Hawaiian Button Up Shirt - Little Essentials - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon5 reviews

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Boys Oxford Button Up Shirt - Lovely Lavender - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon11 reviews

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Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $23.18Original Price: $57.9560% OFF
Star Rating Icon7 reviews

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Mens Dad And Me Striped Poplin Button Up Shirt - Signs of Spring - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon4 reviews

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Boys Matching Family Plaid Poplin Button Up Shirt - All Dressed Up - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon6 reviews

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Boys Fish Button Up Shirt - Splish-Splash - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon6 reviews

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Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon3 reviews

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Mens Matching Family Plaid Poplin Button Up Shirt - All Dressed Up - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon4 reviews

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Boys Striped Linen-Blend Button Up Shirt - Italian Riviera - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon2 reviews

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Boys Dad And Me Striped Poplin Button Up Shirt - Signs of Spring - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon9 reviews

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Boys Chambray Button Up Shirt - Prairie Fields - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon4 reviews

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Mens Dad And Me Plaid Button Up Shirt - Nutcracker - view 1
Sale Price: $16.24Original Price: $64.9575% OFF
Star Rating Icon8 reviews

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Kids Dad And Me Linen-Blend Button Up Shirt - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon10 reviews

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Kids Denim Button Up Shirt - Little Essentials - view 1
Sale Price: $17.08Original Price: $56.9570% OFF
Star Rating Icon7 reviews

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Kids Embroidered Linen-Blend Button Up Shirt - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon5 reviews

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Boys Matching Family Plaid Poplin Button Up Shirt - All Dressed Up - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon3 reviews

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Boys Embroidered Bunny Oxford Button Up Shirt - Enchanted Garden - view 1
Sale Price: $14.24Original Price: $56.9575% OFF
Star Rating Icon8 reviews

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Boys Poplin Button Up Shirt - Special Occasions - view 1
Sale Price: $10.74Original Price: $42.9575% OFF
Star Rating Icon31 reviews

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Kids Embroidered Linen-Blend Button Up Shirt - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon5 reviews

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Mens Dad And Me Striped Linen-Blend Button Up Shirt - view 1
Sale Price: $17.49Original Price: $69.9575% OFF
Star Rating Icon7 reviews

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Boys Plaid Embroidered Fox Flannel Button Up Shirt - Autumn Adventures - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon5 reviews

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Make Every Moment Special with Dressy Shirts

Find the perfect outfit for your little one with Gymboree’s dressy toddler boys shirts. From family gatherings to holiday celebrations or picture day at preschool, each shirt is designed to keep toddlers comfortable while looking adorable. Soft, breathable fabrics feel gentle on sensitive skin, while thoughtful details like tag-free labels, easy snap closures, and flexible fits ensure unrestricted play. Parents love that these tops can be paired with dress pants, boys chinos, or denim for smart-casual styling. With so many colors, patterns, and classic designs, dressing for special occasions becomes easy, fun, and memorable for every little one and their family.

Practical Designs With Playful Details

Gymboree’s dressy shirts combine style and functionality. Button-downs, collared polos, and patterned tops are crafted to fit toddlers perfectly while keeping comfort front and center. From soft stripes and checks to timeless solids like white, navy, and light blue, every shirt works for formal and semi-formal events. These versatile pieces can be layered with sweaters, jackets, or vests, letting parents create complete outfits in minutes. Flexible fits and lightweight fabrics allow toddlers to move freely, play, and celebrate without fuss. Every design balances charm, durability, and practicality, making it a wardrobe staple for parents who value style and comfort.

Complete the Look for Toddler Boys

Make every occasion magical with coordinated toddler boys outfits. Pair dressy shirts with pants, chinos, or denim jeans for a polished look, and add accessories like bow ties, belts, and soft-soled shoes for finishing touches. Gymboree also offers matching sweaters, jackets, and other wardrobe essentials to layer for cooler days while keeping the outfit stylish. Shop Gymboree’s full collection of dressy toddler boys shirts and create effortless bow-to-toe ensembles for birthdays, holidays, or family photos. Every piece is designed to keep toddlers smiling and parents worry-free, making every special moment easy to celebrate in style.

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