Toddler Boys' Button Up Shirts

112Items

Toddler Boys' Button Up Shirts

Free Pick Up Today

Sort By:
Recommended
Boys Gingham Seersucker Button Up Shirt - Nantucket Charm - view 1
Sale Price: $31.46Original Price: $34.9510% OFF

$25.17 WITH CODE EXTRA20

new

CLEARANCE

Boys Plaid Button Up Shirt - Coastal Cutie - view 1
Sale Price: $8.24Original Price: $32.9575% OFF
Star Rating Icon2 reviews

FINAL SALE

$6.59with store pickup only

CLEARANCE

Mens Dad And Me Striped Christmas Tree Poplin Button Up Shirt - view 1
Sale Price: $12.88Original Price: $42.9570% OFF
Star Rating Icon6 reviews

FINAL SALE

Boys Embroidered Flag Seersucker Button Up Shirt - Nantucket Charm - view 1
Sale Price: $40.46Original Price: $44.9510% OFF

$32.37 WITH CODE EXTRA20

CLEARANCE

Boys Plaid Poplin Button Up Shirt - Dino Friends - view 1
Sale Price: $8.24Original Price: $32.9575% OFF
Star Rating Icon3 reviews

FINAL SALE

Most Favorited

CLEARANCE

Boys Dad And Me Striped Christmas Tree Poplin Button Up Shirt - view 1
Sale Price: $8.98Original Price: $29.9570% OFF
Star Rating Icon17 reviews

FINAL SALE

$7.18with store pickup only

CLEARANCE

Boys Schiffli Truck Oxford Button Up Shirt - Dino Friends - view 1
Sale Price: $11.24Original Price: $44.9575% OFF
Star Rating Icon13 reviews

FINAL SALE

Boys Textured Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $38.66Original Price: $42.9510% OFF

    $30.93 WITH CODE EXTRA20

    Most Favorited

    CLEARANCE

    Boys Schiffli Bunny Poplin Button Up Shirt - Blue Belle - view 1
    Sale Price: $10.74Original Price: $42.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $38.66Original Price: $42.9510% OFF

    $30.93 WITH CODE EXTRA20

    new

    CLEARANCE

    Boys Plaid Poplin Button Up Shirt - Little Snowflake - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon4 reviews

    FINAL SALE

    $6.59with store pickup only

    CLEARANCE

    Boys Reindeer Corduroy Button Up Shirt - Holiday Express - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon7 reviews

    FINAL SALE

    CLEARANCE

    Mens Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    $9.99with store pickup only
    Boys Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $31.46Original Price: $34.9510% OFF

    $25.17 WITH CODE EXTRA20

    new

    JUST A FEW LEFT!

    CLEARANCE

    Mens Dad And Me Plaid Poplin Button Up Shirt - Lavender Fields - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon6 reviews

    FINAL SALE

    CLEARANCE

    Boys Matching Family Palm Leaf Button Up Shirt - Little Essentials - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon2 reviews

    FINAL SALE

    Mens Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $37.46Original Price: $49.9525% OFF

    $29.97 WITH CODE EXTRA20

    online only

    CLEARANCE

    Boys Dad And Me Plaid Poplin Button Up Shirt - Lavender Fields - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    CLEARANCE

    Boys Schiffli Reindeer Oxford Button Up Shirt - Holiday Express - view 1
    Sale Price: $11.24Original Price: $44.9575% OFF
    Star Rating Icon7 reviews

    FINAL SALE

    CLEARANCE

    Boys Railroad Striped Seersucker Button Up Shirt - Enchanted Garden - view 1
    Sale Price: $11.98Original Price: $39.9570% OFF

    FINAL SALE

    CLEARANCE

    Mens Dad And Me Gingham Colorblock Poplin Button Up Shirt - Garden Party
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon7 reviews

    FINAL SALE

    Most Favorited

    CLEARANCE

    Boys Striped Train Poplin Button Up Shirt - view 1
    Sale Price: $8.98Original Price: $29.9570% OFF
    Star Rating Icon22 reviews

    FINAL SALE

    $7.18with store pickup only

    CLEARANCE

    Boys Dino Button Up Shirt - Little Essentials - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    CLEARANCE

    Boys Gingham Seersucker Button Up Shirt - Enchanted Garden - view 1
    Sale Price: $11.98Original Price: $39.9570% OFF

    FINAL SALE

    CLEARANCE

    Boys Plaid Luxe Cozy Knit Button Up Shirt - Highland Hills - view 1
    Sale Price: $11.98Original Price: $39.9570% OFF
    Star Rating Icon4 reviews

    FINAL SALE

    CLEARANCE

    Boys Plaid Madras Flannel Button Up Shirt - Holiday Express - view 1
    Sale Price: $11.74Original Price: $46.9575% OFF
    Star Rating Icon11 reviews

    FINAL SALE

    CLEARANCE

    Boys Lemon Poplin Button Up Shirt - Little Essentials - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon2 reviews

    FINAL SALE

    CLEARANCE

    Baby And Toddler Boys Striped Train Poplin Button Up Shirt - view 1
    Sale Price: $8.08Original Price: $26.9570% OFF
    Star Rating Icon14 reviews

    FINAL SALE

    Boys Embroidered Lighthouse Denim Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $24.98Original Price: $49.9550% OFF

    $19.98 WITH CODE EXTRA20

    CLEARANCE

    Kids Plaid Button Up Shirt - Fall Celebrations - view 1
    Sale Price: $10.48Original Price: $34.9570% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    CLEARANCE

    Boys Plaid Poplin Button Up Shirt - Garden Party - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon9 reviews

    FINAL SALE

    Most Favorited

    CLEARANCE

    Boys Schiffli Train Oxford Button Up Shirt - Little Snowflake - view 1
    Sale Price: $11.24Original Price: $44.9575% OFF
    Star Rating Icon16 reviews

    FINAL SALE

    Most Favorited

    CLEARANCE

    Boys Christmas Poplin Button Up Shirt - view 1
    Sale Price: $8.98Original Price: $29.9570% OFF
    Star Rating Icon11 reviews

    FINAL SALE

    Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $22.48Original Price: $44.9550% OFF

    $17.98 WITH CODE EXTRA20

    CLEARANCE

    Boys Embroidered Fox Corduroy Button Up Shirt - Highland Hills - view 1
    Sale Price: $14.98Original Price: $49.9570% OFF
    Star Rating Icon9 reviews

    FINAL SALE

    CLEARANCE

    Baby And Toddler Boys Christmas Poplin Button Up Shirt - view 1
    Sale Price: $8.08Original Price: $26.9570% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    CLEARANCE

    Mens Matching Family Plaid Poplin Button Up Shirt - American Cutie - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon6 reviews

    FINAL SALE

    Boys Embroidered Fish Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $24.98Original Price: $49.9550% OFF

    $19.98 WITH CODE EXTRA20

    CLEARANCE

    Boys Christmas Tree Poplin Button Up Shirt - view 1
    Sale Price: $8.98Original Price: $29.9570% OFF
    Star Rating Icon10 reviews

    FINAL SALE

    Kids Pinstripe Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF

    $13.98 WITH CODE EXTRA20

    TRENDING NOW

    CLEARANCE

    Boys Embroidered Nutcracker Oxford Button Up Shirt - New York City Ballet by GYMBOREE - view 1
    Sale Price: $15.88Original Price: $52.9570% OFF
    Star Rating Icon1 reviews

    FINAL SALE

    CLEARANCE

    Mens Matching Family Plaid Poplin Button Up Shirt - Spring Celebrations - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon6 reviews

    FINAL SALE

    Most Favorited

    CLEARANCE

    Baby And Toddler Boys Reindeer Poplin Button Up Shirt - view 1
    Sale Price: $8.08Original Price: $26.9570% OFF
    Star Rating Icon12 reviews

    FINAL SALE

    Boys Striped Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $24.47Original Price: $34.9530% OFF

    $19.58 WITH CODE EXTRA20

    CLEARANCE

    Boys Schiffli Snow Man Corduroy Button Up Shirt - Royal Christmas - view 1
    Sale Price: $13.48Original Price: $44.9570% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    CLEARANCE

    Boys Flamingo Poplin Button Up Shirt - Seaside Palms - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon2 reviews

    FINAL SALE

    Most Favorited

    CLEARANCE

    Boys Embroidered Santa Corduroy Button Up Shirt - Very Merry - view 1
    Sale Price: $9.24Original Price: $36.9575% OFF
    Star Rating Icon14 reviews

    FINAL SALE

    Boys Striped Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $20.97Original Price: $34.9540% OFF

    $16.78 WITH CODE EXTRA20

    CLEARANCE

    Boys Gingham Flannel Button Up Shirt - First Frost - view 1
    Sale Price: $15.88Original Price: $52.9570% OFF
    Star Rating Icon4 reviews

    FINAL SALE

    CLEARANCE

    Boys Matching Family Plaid Poplin Button Up Shirt - Royal Christmas - view 1
    Sale Price: $9.88Original Price: $32.9570% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    CLEARANCE

    Boys Schiffli Flamingo Button Up Shirt - Seaside Palms - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon9 reviews

    FINAL SALE

    CLEARANCE

    Boys Colorblock Oxford Button Up Shirt - Spring Celebrations - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon15 reviews

    FINAL SALE

    Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF

    $13.98 WITH CODE EXTRA20

    CLEARANCE

    Boys Quilted Scuba Button Up Shirt - First Frost - view 1
    Sale Price: $17.08Original Price: $56.9570% OFF
    Star Rating Icon3 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 Icon4 reviews

    FINAL SALE

    CLEARANCE

    Mens Matching Family Tropical Button Up Shirt - Splish-Splash - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    CLEARANCE

    Mens Matching Family Plaid Poplin Button Up Shirt - A Royal Christmas - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon8 reviews

    FINAL SALE

    Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF

    $15.98 WITH CODE EXTRA20

    Star Rating Icon1 reviews

    CLEARANCE

    Boys Plaid Flannel Button Up Shirt - Royal Christmas - view 1
    Sale Price: $11.98Original Price: $39.9570% OFF
    Star Rating Icon14 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 Icon6 reviews

    FINAL SALE

    CLEARANCE

    Mens Dad And Me Plaid Poplin Button Up Shirt - Lovely Lavender - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    CLEARANCE

    Boys Tropical Button Up Shirt - Splish-Splash - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon7 reviews

    FINAL SALE

    CLEARANCE

    Boys Pinstripe Bunny Poplin Button Up Shirt - Spring Celebrations - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF

    $15.98 WITH CODE EXTRA20

    Star Rating Icon1 reviews

    CLEARANCE

    Boys Plaid Colorblock Flannel Button Up Shirt - Royal Christmas - view 1
    Sale Price: $17.08Original Price: $56.9570% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    Top Rated

    CLEARANCE

    Boys Hawaiian Button Up Shirt - Little Essentials - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    CLEARANCE

    Boys Oxford Button Up Shirt - Lovely Lavender - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon11 reviews

    FINAL SALE

    Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF

    $15.98 WITH CODE EXTRA20

    Star Rating Icon1 reviews

    JUST A FEW LEFT!

    CLEARANCE

    Mens Dad And Me Striped Poplin Button Up Shirt - Signs of Spring - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon4 reviews

    FINAL SALE

    CLEARANCE

    Mens Dad And Me Gingham Button Up Shirt - American Cutie - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon3 reviews

    FINAL SALE

    CLEARANCE

    Boys Fish Button Up Shirt - Splish-Splash - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon6 reviews

    FINAL SALE

    Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $20.97Original Price: $34.9540% OFF

    $16.78 WITH CODE EXTRA20

    CLEARANCE

    Boys Striped Linen-Blend Button Up Shirt - Italian Riviera - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon2 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 Icon4 reviews

    FINAL SALE

    CLEARANCE

    Boys Chambray Button Up Shirt - Prairie Fields - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon4 reviews

    FINAL SALE

    CLEARANCE

    Mens Dad And Me Plaid Button Up Shirt - Nutcracker - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon8 reviews

    FINAL SALE

    $9.99with store pickup only

    Most Favorited

    CLEARANCE

    Boys Embroidered Bunny Oxford Button Up Shirt - Enchanted Garden - view 1
    Sale Price: $13.48Original Price: $44.9570% OFF
    Star Rating Icon8 reviews

    FINAL SALE

    CLEARANCE

    Kids Denim Button Up Shirt - Little Essentials - view 1
    Sale Price: $13.48Original Price: $44.9570% OFF
    Star Rating Icon6 reviews

    FINAL SALE

    CLEARANCE

    Kids Embroidered Linen-Blend Button Up Shirt - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    Top Rated

    Most Favorited

    Mens Dad And Me Striped Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF

    $21.98 WITH CODE EXTRA20

    Star Rating Icon7 reviews

    online only

    CLEARANCE

    Kids Embroidered Linen-Blend Button Up Shirt - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    CLEARANCE

    Boys Plaid Embroidered Fox Flannel Button Up Shirt - Autumn Adventures - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    Most Favorited

    CLEARANCE

    Boys Stain And Wrinkle-Resistant Oxford Button Down Shirt - Uniform - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon23 reviews

    FINAL SALE

    $6.59with store pickup only
    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF

    $21.98 WITH CODE EXTRA20

    Star Rating Icon10 reviews

    online only

    CLEARANCE

    Mens Dad And Me Vacation Linen-Blend Button Up Shirt - Italian Riviera - view 1
    Sale Price: $12.49Original Price: $49.9575% OFF
    Star Rating Icon8 reviews

    FINAL SALE

    CLEARANCE

    Boys Plaid Flannel Button Up Shirt - Autumn Adventures - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon6 reviews

    FINAL SALE

    CLEARANCE

    Boys Bunny Poplin Button Up Shirt - Signs of Spring - view 1
    Sale Price: $9.99Original Price: $39.9575% OFF
    Star Rating Icon7 reviews

    FINAL SALE

    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF

    $21.98 WITH CODE EXTRA20

    Star Rating Icon3 reviews

    online only

    CLEARANCE

    Boys Plaid Poplin Button Up Shirt - Classroom Cutie - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF
    Star Rating Icon5 reviews

    FINAL SALE

    CLEARANCE

    Boys Plaid Button Up Shirt - Country Charm - view 1
    Sale Price: $8.24Original Price: $32.9575% OFF

    FINAL SALE

    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF

    $21.98 WITH CODE EXTRA20

    Star Rating Icon3 reviews

    online only

    Top Rated

    Kids Linen-Blend Button Up Shirt - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF

    $13.98 WITH CODE EXTRA20

    Star Rating Icon14 reviews

    online only

    Page 1 of 2

    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.