Toddler Boys' Button Up Shirts

65Items

Toddler Boys' Button Up Shirts

Shop by category

Sort By:
Recommended

Best Seller

Boys Plaid Flannel Button Up Shirt - Tartan Remix - view 1Boys Plaid Flannel Button Up Shirt - Tartan Remix - view 2
Sale Price: $24.47Original Price: $34.9530% OFF

FINAL SALE!

Best Seller

Top Rated

Boys Plaid Cozy Knit Button Up Shirt - Countryside Manor - view 1Boys Plaid Cozy Knit Button Up Shirt - Countryside Manor - view 2
Sale Price: $27.97Original Price: $39.9530% OFF

FINAL SALE!

Star Rating Icon2 reviews

Best Seller

Boys Plaid Flannel Button Up Shirt - Tartan Remix - view 1Boys Plaid Flannel Button Up Shirt - Tartan Remix - view 2
Sale Price: $24.47Original Price: $34.9530% OFF

FINAL SALE!

Top Rated

Boys Oxford Button Up Shirt - Little Essentials - view 1Boys Oxford Button Up Shirt - Little Essentials - view 2
Sale Price: $23.07Original Price: $32.9530% OFF

FINAL SALE!

Star Rating Icon1 reviews

Best Seller

Boys Plaid Flannel Button Up Shirt - Tartan Remix - view 1Boys Plaid Flannel Button Up Shirt - Tartan Remix - view 2
Sale Price: $24.47Original Price: $34.9530% OFF

FINAL SALE!

Best Seller

Top Rated

Boys Plaid Colorblock Button Up Shirt - Tartan Remix - view 1Boys Plaid Colorblock Button Up Shirt - Tartan Remix - view 2
Sale Price: $27.97Original Price: $39.9530% OFF

FINAL SALE!

Star Rating Icon1 reviews
Boys Button Up Shirt - Little Essentials - view 1Boys Button Up Shirt - Little Essentials - view 2
Sale Price: $24.47Original Price: $34.9530% OFF

FINAL SALE!

Best Seller

Boys Embroidered Button Up Shirt - The Polar Express™ x Gymboree - view 1Boys Embroidered Button Up Shirt - The Polar Express™ x Gymboree - view 2
Sale Price: $34.97Original Price: $49.9530% OFF

FINAL SALE!

Boys Plaid Flannel Button Up Shirt - Countryside Manor - view 1Boys Plaid Flannel Button Up Shirt - Countryside Manor - view 2
Sale Price: $24.47Original Price: $34.9530% OFF

FINAL SALE!

Star Rating Icon2 reviews
Boys Fish Button Up Shirt - Splish-Splash - view 1Boys Fish Button Up Shirt - Splish-Splash - view 2
Sale Price: $8.24Original Price: $32.9575% OFF

FINAL SALE!

Boys Tropical Button Up Shirt - Splish-Splash - view 1Boys Tropical Button Up Shirt - Splish-Splash - view 2
Sale Price: $8.24Original Price: $32.9575% OFF

FINAL SALE!

Boys Tropical Button Up Shirt - Bon Voyage - view 1Boys Tropical Button Up Shirt - Bon Voyage - view 2
Sale Price: $8.24Original Price: $32.9575% OFF

FINAL SALE!

online only

Boys Striped Button Up Shirt - Bon Voyage - view 1Boys Striped Button Up Shirt - Bon Voyage - view 2
Sale Price: $8.74Original Price: $34.9575% OFF

FINAL SALE!

online only

Best Seller

SALE

Boys Plaid Flannel Snap Front Shirt - Blue Sky Mountain - view 1Boys Plaid Flannel Snap Front Shirt - Blue Sky Mountain - view 2
Sale Price: $15.98Original Price: $39.9560% OFF

FINAL SALE

SALE

Boys Textured Corduroy Button Up Shirt - The Harvest Edit - view 1Boys Textured Corduroy Button Up Shirt - The Harvest Edit - view 2
Sale Price: $18.78Original Price: $46.9560% OFF

FINAL SALE

Best Seller

SALE

Boys Embroidered Horse Flannel Snap Front Shirt - Blue Sky Mountain - view 1Boys Embroidered Horse Flannel Snap Front Shirt - Blue Sky Mountain - view 2
Sale Price: $17.98Original Price: $44.9560% OFF
Star Rating Icon1 reviews

FINAL SALE

SALE

Boys Embroidered Tropical Leaf Gauze Button Up Shirt - Amalfi Coast - view 1Boys Embroidered Tropical Leaf Gauze Button Up Shirt - Amalfi Coast - view 2
Sale Price: $17.18Original Price: $42.9560% OFF
Star Rating Icon1 reviews

FINAL SALE

SALE

Boys Embroidered Tropical Leaf Linen-Blend Button Up Shirt - Amalfi Coast - view 1Boys Embroidered Tropical Leaf Linen-Blend Button Up Shirt - Amalfi Coast - view 2
Sale Price: $17.18Original Price: $42.9560% OFF

FINAL SALE

SALE

Boys Embroidered Beach Button Up Shirt - Amalfi Coast - view 1Boys Embroidered Beach Button Up Shirt - Amalfi Coast - view 2
Sale Price: $17.18Original Price: $42.9560% OFF
Star Rating Icon1 reviews

FINAL SALE

SALE

Boys Matching Family Plaid Twill Button Up Shirt - view 1Boys Matching Family Plaid Twill Button Up Shirt - view 2
Sale Price: $13.18Original Price: $32.9560% OFF
Star Rating Icon5 reviews

FINAL SALE

SALE

Mens Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1Mens Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon5 reviews

FINAL SALE

JUST A FEW LEFT!

SALE

Boys Striped Train Poplin Button Up Shirt - view 1Boys Striped Train Poplin Button Up Shirt - view 2
Sale Price: $11.98Original Price: $29.9560% OFF
Star Rating Icon22 reviews

FINAL SALE

SALE

Boys Textured Corduroy Button Up Shirt - The Harvest Edit - view 1Boys Textured Corduroy Button Up Shirt - The Harvest Edit - view 2
Sale Price: $18.78Original Price: $46.9560% OFF

FINAL SALE

SALE

Boys Textured Button Up Shirt - Driftwood Bay - view 1Boys Textured Button Up Shirt - Driftwood Bay - view 2
Sale Price: $17.18Original Price: $42.9560% OFF

FINAL SALE

SALE

Boys Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1Boys Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 2
Sale Price: $13.98Original Price: $34.9560% OFF
Star Rating Icon4 reviews

FINAL SALE

SALE

Boys Railroad Striped Seersucker Button Up Shirt - Enchanted Garden - view 1Boys Railroad Striped Seersucker Button Up Shirt - Enchanted Garden - view 2
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon2 reviews

FINAL SALE

SALE

Boys Gingham Seersucker Button Up Shirt - Enchanted Garden - view 1Boys Gingham Seersucker Button Up Shirt - Enchanted Garden - view 2
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon1 reviews

FINAL SALE

SALE

Boys Dino Button Up Shirt - Little Essentials - view 1Boys Dino Button Up Shirt - Little Essentials - view 2
Sale Price: $13.18Original Price: $32.9560% OFF
Star Rating Icon5 reviews

FINAL SALE

SALE

Boys Hawaiian Button Up Shirt - Little Essentials - view 1Boys Hawaiian Button Up Shirt - Little Essentials - view 2
Sale Price: $13.18Original Price: $32.9560% OFF

FINAL SALE

SALE

Boys Flamingo Poplin Button Up Shirt - Seaside Palms - view 1Boys Flamingo Poplin Button Up Shirt - Seaside Palms - view 2
Sale Price: $13.18Original Price: $32.9560% OFF

FINAL SALE

SALE

Boys Lemon Poplin Button Up Shirt - Little Essentials - view 1Boys Lemon Poplin Button Up Shirt - Little Essentials - view 2
Sale Price: $13.18Original Price: $32.9560% OFF

FINAL SALE

SALE

Boys Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 1Boys Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 2
Sale Price: $13.18Original Price: $32.9560% OFF
Star Rating Icon2 reviews

FINAL SALE

SALE

Boys Schiffli Flamingo Button Up Shirt - Seaside Palms - view 1Boys Schiffli Flamingo Button Up Shirt - Seaside Palms - view 2
Sale Price: $15.98Original Price: $39.9560% OFF

FINAL SALE

SALE

Mens Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 1Mens Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon3 reviews

FINAL SALE

SALE

Mens Matching Family Tropical Button Up Shirt - Splish-Splash - view 1Mens Matching Family Tropical Button Up Shirt - Splish-Splash - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon3 reviews

FINAL SALE

SALE

Mens Dad And Me Plaid Poplin Button Up Shirt - Lovely Lavender - view 1Mens Dad And Me Plaid Poplin Button Up Shirt - Lovely Lavender - view 2
Sale Price: $19.98Original Price: $49.9560% OFF

FINAL SALE

SALE

Mens Matching Family Plaid Poplin Button Up Shirt - Spring Celebrations - view 1Mens Matching Family Plaid Poplin Button Up Shirt - Spring Celebrations - view 2
Sale Price: $19.98Original Price: $49.9560% OFF

FINAL SALE

SALE

Mens Dad And Me Striped Poplin Button Up Shirt - Signs of Spring - view 1Mens Dad And Me Striped Poplin Button Up Shirt - Signs of Spring - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon4 reviews

FINAL SALE

SALE

Boys Bunny Poplin Button Up Shirt - Signs of Spring - view 1Boys Bunny Poplin Button Up Shirt - Signs of Spring - view 2
Sale Price: $15.98Original Price: $39.9560% OFF

FINAL SALE

SALE

Boys Chambray Button Up Shirt - Prairie Fields - view 1Boys Chambray Button Up Shirt - Prairie Fields - view 2
Sale Price: $15.98Original Price: $39.9560% OFF

FINAL SALE

SALE

Boys Oxford Button Up Shirt - Lovely Lavender - view 1Boys Oxford Button Up Shirt - Lovely Lavender - view 2
Sale Price: $13.18Original Price: $32.9560% OFF
Star Rating Icon11 reviews

FINAL SALE

SALE

Boys Colorblock Oxford Button Up Shirt - Spring Celebrations - view 1Boys Colorblock Oxford Button Up Shirt - Spring Celebrations - view 2
Sale Price: $15.98Original Price: $39.9560% OFF

FINAL SALE

SALE

Boys Pinstripe Bunny Poplin Button Up Shirt - Spring Celebrations - view 1Boys Pinstripe Bunny Poplin Button Up Shirt - Spring Celebrations - view 2
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon3 reviews

FINAL SALE

SALE

Mens Dad And Me Plaid Button Up Shirt - Nutcracker - view 1Mens Dad And Me Plaid Button Up Shirt - Nutcracker - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon8 reviews

FINAL SALE

SALE

Mens Matching Family Plaid Button Up Shirt - Christmas Cabin - view 1Mens Matching Family Plaid Button Up Shirt - Christmas Cabin - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon1 reviews

FINAL SALE

SALE

Boys Plaid Twill Snap Front Shirt - Rustic Ranch - view 1Boys Plaid Twill Snap Front Shirt - Rustic Ranch - view 2
Sale Price: $15.98Original Price: $39.9560% OFF

FINAL SALE

SALE

Boys Plaid Poplin Button Up Shirt - Parisian Chic - view 1Boys Plaid Poplin Button Up Shirt - Parisian Chic - view 2
Sale Price: $13.18Original Price: $32.9560% OFF
Star Rating Icon2 reviews

FINAL SALE

SALE

Mens Matching Family Plaid Twill Button Up Shirt - view 1Mens Matching Family Plaid Twill Button Up Shirt - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon5 reviews

FINAL SALE

Most Favorited

SALE

Boys Christmas Poplin Button Up Shirt - view 1Boys Christmas Poplin Button Up Shirt - view 2
Sale Price: $11.98Original Price: $29.9560% OFF
Star Rating Icon11 reviews

FINAL SALE

SALE

Boys Christmas Tree Poplin Button Up Shirt - view 1Boys Christmas Tree Poplin Button Up Shirt - view 2
Sale Price: $11.98Original Price: $29.9560% OFF

FINAL SALE

SALE

Mens Dad And Me Striped Christmas Tree Poplin Button Up Shirt - view 1Mens Dad And Me Striped Christmas Tree Poplin Button Up Shirt - view 2
Sale Price: $17.18Original Price: $42.9560% OFF

FINAL SALE

Most Favorited

SALE

Boys Dad And Me Striped Christmas Tree Poplin Button Up Shirt - view 1Boys Dad And Me Striped Christmas Tree Poplin Button Up Shirt - view 2
Sale Price: $11.98Original Price: $29.9560% OFF
Star Rating Icon17 reviews

FINAL SALE

SALE

Baby And Toddler Boys Striped Train Poplin Button Up Shirt - view 1Baby And Toddler Boys Striped Train Poplin Button Up Shirt - view 2
Sale Price: $10.78Original Price: $26.9560% OFF
Star Rating Icon14 reviews

FINAL SALE

Most Favorited

SALE

Baby And Toddler Boys Christmas Poplin Button Up Shirt - view 1Baby And Toddler Boys Christmas Poplin Button Up Shirt - view 2
Sale Price: $10.78Original Price: $26.9560% OFF
Star Rating Icon5 reviews

FINAL SALE

Most Favorited

SALE

Baby And Toddler Boys Reindeer Poplin Button Up Shirt - view 1Baby And Toddler Boys Reindeer Poplin Button Up Shirt - view 2
Sale Price: $10.78Original Price: $26.9560% OFF
Star Rating Icon12 reviews

FINAL SALE

SALE

Mens Matching Family Plaid Poplin Button Up Shirt - A Royal Christmas - view 1Mens Matching Family Plaid Poplin Button Up Shirt - A Royal Christmas - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon8 reviews

FINAL SALE

SALE

Boys Gingham Twill Button Up Shirt - Montana Mountain - view 1Boys Gingham Twill Button Up Shirt - Montana Mountain - view 2
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon4 reviews

FINAL SALE

SALE

Boys Wrinkle-Resistant Oxford Button Up Shirt - Uniform - view 1Boys Wrinkle-Resistant Oxford Button Up Shirt - Uniform - view 2
Sale Price: $10.78Original Price: $26.9560% OFF
Star Rating Icon7 reviews

FINAL SALE

SALE

Mens Matching Family Plaid Poplin Button Up Shirt - American Cutie - view 1Mens Matching Family Plaid Poplin Button Up Shirt - American Cutie - view 2
Sale Price: $19.98Original Price: $49.9560% OFF

FINAL SALE

SALE

Mens Matching Family Flamingo Button Up Shirt - Tropical Paradise - view 1Mens Matching Family Flamingo Button Up Shirt - Tropical Paradise - view 2
Sale Price: $19.98Original Price: $49.9560% OFF

FINAL SALE

SALE

Boys Matching Family Flamingo Button Up Shirt - Tropical Paradise - view 1Boys Matching Family Flamingo Button Up Shirt - Tropical Paradise - view 2
Sale Price: $13.18Original Price: $32.9560% OFF

FINAL SALE

SALE

Mens Matching Family Plaid Button Up Shirt - Family Celebrations - view 1Mens Matching Family Plaid Button Up Shirt - Family Celebrations - view 2
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon9 reviews

FINAL SALE

SALE

Boys Airplane Button Up Top - Aviator School - view 1Boys Airplane Button Up Top - Aviator School - view 2
Sale Price: $14.78Original Price: $36.9560% OFF
Star Rating Icon10 reviews

FINAL SALE

SALE

Boys Stain And Wrinkle-Resistant Oxford Button Down Shirt - Uniform - view 1Boys Stain And Wrinkle-Resistant Oxford Button Down Shirt - Uniform - view 2
Sale Price: $13.18Original Price: $32.9560% OFF

FINAL SALE

SALE

Boys Stain And Wrinkle-Resistant Oxford Button Down Shirt - Uniform - view 1Boys Stain And Wrinkle-Resistant Oxford Button Down Shirt - Uniform - view 2
Sale Price: $13.18Original Price: $32.9560% OFF

FINAL SALE

Page 1 of 1

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.


Frequently Asked Questions (FAQs):

What are dressy toddler boys shirts?

Dressy toddler boys shirts include button-down shirts and polished tops designed for more formal occasions and styled outfits.

When should toddlers wear dressy shirts?

These styles are perfect for family events, holidays, celebrations and photo-ready moments.

Are dressy shirts comfortable for toddlers?

Yes, they are designed with soft fabrics and easy fits to ensure comfort while maintaining a polished appearance.

How can dressy toddler shirts be styled?

They pair well with chinos, dress shorts or coordinated sets for a refined, put-together look.