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Toddler Boy Fall Outfit | Denim Overalls & Retro 90s Look for Boys

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Pin graphic titled 'Toddler Boy Fall Outfit: 90s Overalls Look' showing Levi's denim overalls, a navy and white wide stripe tee, and white canvas high-top sneakers on a tan linen background.
Pinned from The Mom Mode Mindset

My son picked these overalls off the rack himself because he liked clicking the buckles, not because overalls are having a moment again. Underneath a striped tee and finished with real high tops instead of his usual light-up sneakers, it turned into the easiest outfit I've thrown together all season, and nobody had to negotiate over what shirt went under it.

  1. Light wash Levi's toddler denim overalls with metal clasp straps and a front bib pocket.

    Levi's Toddler Overall, Basil Sky

    Real metal clasps instead of snaps, and a wash that already looks lived-in so new stains blend right in.

    ~$29Shop it
  2. Toddler tee with wide navy and white horizontal stripes and a navy crew neck.

    Wide Stripe Long Sleeve Tee

    Bold enough to read in a photo from across the room, plain enough to wear on repeat.

    ~$15Shop it
  3. White canvas toddler high-top sneaker with silver eyelets, white laces, and a white rubber sole.

    Canvas High-Top Sneakers, White

    A little extra height on the sole for however many puddles are still around this time of year.

    ~$25Shop it

Common questions

What sizes does this outfit run?
Overalls and the tee run true to size in toddler sizing, the sneakers run about a half size big.
Is this warm enough for cooler fall days?
Layer a long sleeve or thermal underneath the overalls once it gets colder, the tee alone is best for milder days.
Can I dress this up?
Swap the high tops for boots and it moves easily from a playground afternoon to fall family photos.

The buckles are still the best part, according to him.