UrbanSitter’s Back to School Handbook: Part 2 – Send Them Back to School in Style

We’ve made your back-to-school shopping list as easy as clicking on our favorite pins and deciding which you’ll choose to outfit and arm your little one for the new school year. Whether he or she is off to preschool or grade school, we’ve got you covered with super cute, hard working staples. Check out our Back to School Style Pinterest board or this list:

  1. Leave it in the hands of a professional by subscribing to this groovy service that mails your little one a coolest-of-the-cool outfit each month. You complete a style survey to help stylists choose a look that’s just right.
  2. Little Man will be tearing up the playground with these stylish new kicks by Keen.
  3. Protect your investment by labeling everything from jackets to sippy cups and water bottles with these trendy, no-one-can-call babyish, and totally waterproof labels.
  4. Lunch boxes have come a long way since we were kids. Try the bento route this year with one of these slick, eco-friendly.
  5. Who can’t relate to the ickiness of transitioning from summer flip flops to stuffy socks and sneakers? Avoid sock meltdowns with these soft, seamless, no-binding organic socks that beat plain white ones any day.
  6. For times when a t-shirt won’t do, give him a blazer with some ‘tude.
  7. When the weather’s still a bit steamy, these easy, breezy skirts make the grade.
  8. Preschoolers need backpacks, too. You can ease their load with one of these little-kid sized picks from SkipHop.
  9. Isaac Mizrahi supposedly goes to Estella for inspiration. Maybe you should, too.
  10. For preschoolers who are lucky enough to have quiet time at school, this nap mat we found on Etsy looks as good as it feels.

Follow UrbanSitter on Pinterest! Missed the Back to School Handbook Part 1? Find out how to Tame the Morning Chaos.