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Toddler Boys' Button Up Shirts

30Items

Toddler Boys' Button Up Shirts

Boys Gingham Seersucker Button Up Shirt - Nantucket Charm
    Price: $34.95
    Boys Embroidered Flag Seersucker Button Up Shirt - Nantucket Charm
    Price: $44.95

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    Boys Textured Button Up Shirt - Driftwood Bay
      Price: $42.95
      Boys Striped Textured Button Up Shirt - Driftwood Bay
      Price: $42.95

      new

      Boys Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit
      Price: $34.95

      new

      Mens Matching Family Paisley Linen-Blend Button Up Shirt - Linen Edit
      Price: $49.95

      online only

      Boys Railroad Striped Seersucker Button Up Shirt - Enchanted Garden
      Price: $29.96

      $23.97 WITH CODE EXTRA20

      EARN DOUBLE/TRIPLE POINTS on Easter Styles!
      Boys Gingham Seersucker Button Up Shirt - Enchanted Garden
      Price: $23.97

      $19.18 WITH CODE EXTRA20

      EARN DOUBLE/TRIPLE POINTS on Easter Styles!

      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.