Toddler Boys' Button Up Shirts

34Items

Toddler Boys' Button Up Shirts

Free Pick Up Today

Sort By:
Recommended

Top Rated

Boys Gingham Seersucker Button Up Shirt - Nantucket Charm - view 1
Sale Price: $13.98Original Price: $34.9560% OFF
Star Rating Icon2 reviews
Boys Embroidered Flag Seersucker Button Up Shirt - Nantucket Charm - view 1
Sale Price: $17.98Original Price: $44.9560% OFF
Boys Embroidered Beach Button Up Shirt - Amalfi Coast - view 1
Sale Price: $17.18Original Price: $42.9560% OFF
Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
Sale Price: $17.18Original Price: $42.9560% OFF
Boys Embroidered Tropical Leaf Gauze Button Up Shirt - Amalfi Coast - view 1
Sale Price: $17.18Original Price: $42.9560% OFF
Boys Embroidered Tropical Leaf Linen-Blend Button Up Shirt - Amalfi Coast - view 1
Sale Price: $17.18Original Price: $42.9560% OFF
Boys Embroidered Tropical Leaf Linen-Blend Button Up Shirt - Amalfi Coast - view 1
Sale Price: $17.18Original Price: $42.9560% OFF

CLEARANCE

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

FINAL SALE

CLEARANCE

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

FINAL SALE

Most Favorited

CLEARANCE

Kids Linen-Blend Button Up Shirt - view 1
Sale Price: $8.74Original Price: $34.9575% OFF
Star Rating Icon22 reviews

FINAL SALE

CLEARANCE

Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $13.98Original Price: $34.9560% OFF
Star Rating Icon9 reviews

FINAL SALE

CLEARANCE

Kids Pinstripe Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $13.98Original Price: $34.9560% OFF
Star Rating Icon1 reviews

FINAL SALE

CLEARANCE

Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon7 reviews

FINAL SALE

CLEARANCE

Kids Linen-Blend Button Up Shirt - view 1
Sale Price: $8.74Original Price: $34.9575% OFF
Star Rating Icon22 reviews

FINAL SALE

Most Favorited

CLEARANCE

Mens Dad And Me Striped Linen-Blend Button Up Shirt - view 1
Sale Price: $13.74Original Price: $54.9575% OFF
Star Rating Icon7 reviews

FINAL SALE

CLEARANCE

Mens Dad And Me Linen-Blend Button Up Shirt - view 1
Sale Price: $13.74Original Price: $54.9575% OFF
Star Rating Icon3 reviews

FINAL SALE

CLEARANCE

Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon7 reviews

FINAL SALE

CLEARANCE

Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $13.98Original Price: $34.9560% OFF
Star Rating Icon9 reviews

FINAL SALE

CLEARANCE

Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
Sale Price: $15.98Original Price: $39.9560% OFF
Star Rating Icon7 reviews

FINAL SALE

CLEARANCE

Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
Sale Price: $17.98Original Price: $44.9560% OFF
Star Rating Icon2 reviews

FINAL SALE

CLEARANCE

Mens Dad And Me Linen-Blend Button Up Shirt - view 1
Sale Price: $13.74Original Price: $54.9575% OFF
Star Rating Icon4 reviews

FINAL SALE

CLEARANCE

Mens Dad And Me Linen-Blend Button Up Shirt - view 1
Sale Price: $13.74Original Price: $54.9575% OFF
Star Rating Icon4 reviews

FINAL SALE

CLEARANCE

Mens Dad And Me Linen-Blend Button Up Shirt - view 1
Sale Price: $13.74Original Price: $54.9575% OFF
Star Rating Icon10 reviews

FINAL SALE

CLEARANCE

Mens Dad And Me Gingham Colorblock Poplin Button Up Shirt - Garden Party - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon9 reviews

FINAL SALE

CLEARANCE

Boys Embroidered Lighthouse Denim Button Up Shirt - Driftwood Bay - view 1
Sale Price: $19.98Original Price: $49.9560% OFF
Star Rating Icon3 reviews

FINAL SALE

CLEARANCE

Boys Gingham Flannel Button Up Shirt - First Frost - view 1
Sale Price: $15.88Original Price: $52.9570% OFF
Star Rating Icon5 reviews

FINAL SALE

CLEARANCE

Boys Embroidered Fish Button Up Shirt - Driftwood Bay - view 1
Sale Price: $19.98Original Price: $49.9560% OFF

FINAL SALE

CLEARANCE

Boys Plaid Colorblock Flannel Button Up Shirt - Royal Christmas - view 1
Sale Price: $17.08Original Price: $56.9570% OFF
Star Rating Icon4 reviews

FINAL SALE

CLEARANCE

Boys Schiffli Truck Oxford Button Up Shirt - Dino Friends - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon14 reviews

FINAL SALE

CLEARANCE

Mens Matching Family Plaid Poplin Button Up Shirt - Royal Christmas - view 1
Sale Price: $14.98Original Price: $49.9570% OFF
Star Rating Icon6 reviews

FINAL SALE

JUST A FEW LEFT!

CLEARANCE

Boys Quilted Scuba Button Up Shirt - First Frost - view 1
Sale Price: $17.08Original Price: $56.9570% OFF
Star Rating Icon4 reviews

FINAL SALE

Most Favorited

CLEARANCE

Boys Embroidered Bunny Oxford Button Up Shirt - Enchanted Garden - view 1
Sale Price: $17.98Original Price: $44.9560% OFF
Star Rating Icon8 reviews

FINAL SALE

CLEARANCE

Boys Schiffli Snow Man Corduroy Button Up Shirt - Royal Christmas - view 1
Sale Price: $13.48Original Price: $44.9570% OFF
Star Rating Icon6 reviews

FINAL SALE

CLEARANCE

Mens Matching Family Plaid Poplin Button Up Shirt - All Dressed Up - view 1
Sale Price: $12.49Original Price: $49.9575% OFF
Star Rating Icon7 reviews

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.