30Items

Free Pick Up Today

Sort By:
Recommended
Boys Gingham Seersucker Button Up Shirt - Nantucket Charm - view 1
Sale Price: $17.48Original Price: $34.9550% OFF

new

Boys Embroidered Flag Seersucker Button Up Shirt - Nantucket Charm - view 1
Sale Price: $22.48Original Price: $44.9550% OFF

new

Boys Textured Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $21.48Original Price: $42.9550% OFF
    Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $21.48Original Price: $42.9550% OFF

    new

    Boys Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF

    new

    Mens Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $24.98Original Price: $49.9550% OFF

    online only

    Boys Railroad Striped Seersucker Button Up Shirt - Enchanted Garden - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Boys Gingham Seersucker Button Up Shirt - Enchanted Garden - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Boys Embroidered Lighthouse Denim Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $24.98Original Price: $49.9550% OFF
    Boys Striped Textured Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $22.48Original Price: $44.9550% OFF
    Boys Embroidered Fish Button Up Shirt - Driftwood Bay - view 1
    Sale Price: $24.98Original Price: $49.9550% OFF
    Kids Pinstripe Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF
    Boys Striped Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF
    Boys Striped Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF
    Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF
    Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon1 reviews
    Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon1 reviews
    Boys Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $19.98Original Price: $39.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon1 reviews
    Kids Linen-Blend Button Up Shirt - Linen Edit - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF

    Top Rated

    Most Favorited

    Boys Embroidered Bunny Oxford Button Up Shirt - Enchanted Garden - view 1
    Sale Price: $22.48Original Price: $44.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon8 reviews

    Top Rated

    Most Favorited

    Mens Dad And Me Striped Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon7 reviews

    online only

    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon10 reviews

    online only

    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon3 reviews

    online only

    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon3 reviews

    online only

    Kids Linen-Blend Button Up Shirt - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon11 reviews

    online only

    Kids Linen-Blend Button Up Shirt - view 1
    Sale Price: $17.48Original Price: $34.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon11 reviews

    online only

    Mens Dad And Me Linen-Blend Button Up Shirt - view 1
    Sale Price: $27.48Original Price: $54.9550% OFF
    EARN DOUBLE/TRIPLE POINTS on Easter Styles!
    Star Rating Icon3 reviews

    online only

    Top Rated

    Boys Wrinkle-Resistant Oxford Button Up Shirt - Uniform - view 1
    Sale Price: $13.48Original Price: $26.9550% OFF
    Star Rating Icon4 reviews
    $10.78with store pickup only

    TRENDING NOW

    Top Rated

    Boys Wrinkle Resistant Button Down Shirt - Uniform - view 1
    Sale Price: $16.48Original Price: $32.9550% OFF
    Star Rating Icon11 reviews

    online only

    Top Rated

    Boys Wrinkle Resistant Button Down Shirt - Uniform - view 1
    Sale Price: $16.48Original Price: $32.9550% OFF
    Star Rating Icon11 reviews

    online only

    $13.18with store pickup only
    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.