Toddler Boys' Button Up Shirts

20Items

Toddler Boys' Button Up Shirts

Boys Embroidered Nutcracker Oxford Button Up Shirt - New York City Ballet by GYMBOREE
Price: $31.77
Boys Schiffli Snow Man Corduroy Button Up Shirt - Royal Christmas
Price: $44.95

$17.98 60% OFF W/CODE CYBER60

EARN DOUBLE/TRIPLE POINTS on Royal Christmas & Gymmies Styles!
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Boys Matching Family Plaid Poplin Button Up Shirt - Royal Christmas
Price: $32.95

$13.18 60% OFF W/CODE CYBER60

EARN DOUBLE/TRIPLE POINTS on Royal Christmas & Gymmies Styles!
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Mens Matching Family Plaid Poplin Button Up Shirt - Royal Christmas
Price: $49.95

$19.98 60% OFF W/CODE CYBER60

EARN DOUBLE/TRIPLE POINTS on Royal Christmas & Gymmies Styles!

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Boys Plaid Flannel Button Up Shirt - Royal Christmas
Price: $39.95

$15.98 60% OFF W/CODE CYBER60

EARN DOUBLE/TRIPLE POINTS on Royal Christmas & Gymmies Styles!
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Boys Plaid Colorblock Flannel Button Up Shirt - Royal Christmas
Price: $56.95

$22.78 60% OFF W/CODE CYBER60

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Boys Gingham Flannel Button Up Shirt - First Frost
Price: $52.95

$21.18 60% OFF W/CODE CYBER60

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Boys Quilted Scuba Button Up Shirt - First Frost
Price: $56.95

$22.78 60% OFF W/CODE CYBER60

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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.