Creating unique and affordable outfit ideas for each sweet season in your child's life

How to: Transition into Fall Weather (Fall Fashion Outfits for Boys)

August is quickly approaching and we all know what that means – school is just around the corner (and all my teacher friends just cringed). But as a student, I LOVED back-to-school shopping. It was the beginning of a new academic year, a fresh slate. My mom and I would make a special trip to Target for brand-new supplies and the mall for some fall fashion finds.


While I enjoyed the tradition of back-to-school shopping as a student, I have found it more challenging as a parent. If your kids are anything like mine, they grow at the speed of light. How am I supposed to buy new clothes for the school year in smoldering August temps and cross my fingers that they fit by the time the weather cools down?


Good news!! I have put together multiple looks for boys that are fantastic for transitional weather. These pieces mix and match with ease and still look polished. My recommendation for boys back-to-school shopping? Spend your money on a few classic staples and fresh shoes; hold off on new sweatpants and jeans until you actually need them.


Happy ” fall fashion” shopping for your boys!!

  1. Jean Jacket
    • denim is very trendy right now and what better way to enter fall than a classic denim jacket
  2. Striped t-shirt
    • have and LOVE. Soft material, charcoal gray color with a couple buttons – one of my favorites
  3. Black Jeans
    • black jeans are a staple for all my kids; love the dark wash look on my boys
    • I sometimes roll up the bottom and style with sandals if I’m not quite ready to succumb to boot weather.
  4. Beige cloud slippers
    • Was not sure how much my son would like these but ended up being his go-to shoe all summer; will still be pertinent transitioning into fall
  5. Black plaid shirt
    • just ordered – can’t want to style this in the fall
  6. Tank Top set
    • simple classic for layering
  7. Jean shorts
    • love these from Zara
  8. White sneakers
    • any white shoe will do; I try to find a little cheaper options because my boys are hard on shoes
    • I like these from H&M.
  9. White long sleeve t-shirt
    • I should buy stock in these. Have in multiple sizes and multiple colors but white (and black) are my favorite and most used.
  10. Green shorts
    • my favorite Target buy for boys this summer
    • The “above the knee” version is sold out but they do still have the “at the knee” available in all sizes!
  11. Vans -boots
    • If you’re going to splurge on something, this is it.
    • I do keep these separate from play shoes – we use for church, family pictures, parties and other events.
  12. Gray sweatshirt
    • classic, simple, used daily over here and have in multiple sizes
  13. White t-shirt
    • just another classic staple
  14. Black shorts
    • soft and multi-functional
  15. Gray hoodie
    • What can I say? I love a gray sweatshirt (and so do my boys).
  16. Vans -shoe
    • Don’t own BUT 👀
  17. Nike t-shirt
    • If your son is a Nike kid, love this top!
  18. Nike socks
    • classic staple
  19. Green sleeveless hoodie
    • Wal-Mart fine!
    • Check it out here.
  20. Adidas shoes
    • another sportier white sneaker option if you’re not into the H&M shoes
  21. Gray sweatpants
    • will order when weather cools down
  22. Black checkered shirt
    • fun, layering piece from Wal-Mart

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