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BACK-TO-SCHOOL BOX SHIPPING NOW
Starting at $99 · Always ships free
Style

A pair of sneakers. A pair of play shoes. Expertly chosen for the season—and your child.

Keeping up with growing feet just got easier. Our 2-Shoe Seasonal Box includes 2 high-quality pairs: comfy, everyday sneakers and versatile play shoes that can be dressed up or down. Each pair is handpicked to match your child’s size, age, and developmental stage—so they’re ready for the playground and picture day.

Curated by moms and footwear experts, Fitted makes shoe shopping simple, stylish, and stress-free. Get started with a single box or enjoy the ease of automatic seasonal deliveries—your choice.

📏 Need help with sizing?

Want to double-check sizing? Email us—a quick photo helps, and we’re happy to confirm before your box ships.

📦 Want the full experience? 

Add a pair of rain boots with our 3-Shoe Seasonal Box →

✨ Just a heads up:

Images show examples of our boxes. Your child’s shoes will be just as stylish—handpicked just for them! Have something in mind? Feel free to include special requests when placing your order—we love personalizing. It’s what we do!

We'll automatically size your children up ½ to a full size every season, or feel free to update your sizing at least one month before your next box ships.

Questions about sizing? Your first box includes a handy sizing tool. Plus our team is happy to help advise on the best size for your kids. Contact us at hello@fittedfamily.com.

Right now, we are shipping our Sunny Days Box which includes sneakers, sandals and water shoes perfect for those warm adventures.

With each delivery, you will receive a fresh mix of shoes plus special surprises in each box!

Subscription orders will bill in the month prior to the next box shipping.

Back to School Boxes ship in August, Holiday Boxes ship in November, and Sunny Days Boxes ship in March.

You may cancel your subscription at any time. Please see Customer Service Page for details.

Each box is curated to your child's age and the season. Our amazing brands include:

  • BOGS
  • Cienta
  • EMU Australia
  • Footmates 
  • Hunter Boots
  • KEEN
  • Merrell
  • Native Shoes
  • See Kai Run
  • Tsukihoshi 

With more exciting additions each season!

2-Shoe Seasonal Box (Ages 0–7)
Style
  • Style: Boys

How it works

  • Sunny Days

    Delivers beginning in March

    (orders accepted through June)

    Includes warm weather essentials: sneakers, sandals, and water shoes

  • Back to School

    Delivers beginning in July

    (orders accepted through September)

    Features shoes perfect for every day: sneakers, play shoes, and rain boots

  • Holidays

    Delivers beginning in November

    (orders accepted through February)

    For festive months and cooler temps: sneakers, dress shoes, and winter boots

Discover Incredible value

At Fitted, we believe in simplicity, transparency, and value. Our subscription service pricing is straightforward and based on the combined Manufacturer's Suggested Retail Price (MSRP) of the pairs of shoes. With Fitted, you not only get top-notch shoes for your little ones but also peace of mind knowing that you're getting the best value for your money. And, shipping is free!