September 2023- Back to School, But Make It Cool
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Back-to-school season always sneaks up on me. One minute, we’re living our best lives at the beach, and the next, I’m staring at supply lists that look like they’re prepping for a small office startup. But beyond pencils and glue sticks, there’s another piece of the puzzle that can make or break the first day: the outfit.
Kids might pretend they don’t care what they wear, but trust me — when they feel good in their clothes, it shows. Confidence matters just as much as comfort when it comes to school mornings. That’s where the “cool” comes in.
The Morning Hustle is Real
Let’s be honest: mornings during the school year are basically an Olympic event. You’re trying to get four kids fed, packed, brushed, and dressed before the bus arrives — all while remembering where you put your coffee.
The secret to keeping mornings manageable is simple: outfits that don’t require thought. Pieces that mix, match, and layer without turning into a fight. That’s why I love building wardrobes that are functional, versatile, and still full of personality.
Key Pieces to Invest In
Here’s what I swear by for back-to-school wardrobes that work:
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Shackets (shirt + jacket): They’re the unsung heroes of transitional weather. Light enough for warm afternoons, layered enough for chilly mornings.
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Comfy hoodies: Bonus points if they’re moto or skate-inspired. They’re playground-proof and stylish enough for picture day.
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Soft joggers or cargo pants: Forget stiff jeans that make kids squirm at their desks. Joggers give them freedom to move without sacrificing style.
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Graphic tees: Personality on a shirt. Easy to throw on, fun to layer, and always kid-approved.
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Sneakers: A must. Skater-style kicks work with everything — and last longer than you’d expect.
These pieces aren’t about chasing trends — they’re about setting your kid up for success every single day.
Layering for Comfort + Style
The key to back-to-school dressing? Layers.
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A neutral tee + checkered flannel = cool but not fussy.
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Hoodie under a denim jacket = instant style upgrade.
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Joggers with a moto tee + bomber jacket = little rebel energy on point.
Layers let kids adapt to classrooms, playgrounds, and weather changes without needing five outfit changes a day.
3 Ways to Simplify School-Day Outfits
Because sometimes, fashion has to meet reality. Here are my go-to hacks:
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Create a mini capsule. Pick 7–10 mix-and-match items that work together. Fewer options = faster mornings.
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Set outfits the night before. Seriously, it saves so much stress. Let kids pick their combo, and mornings are smoother.
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Let them own it. Giving kids a say in what they wear (within reason) makes them way more cooperative. Trust me, it’s worth the extra two minutes of “debating” between hoodies.
Why “Cool” Matters
Here’s the thing: “cool” isn’t about being trendy. It’s about kids feeling confident and comfortable in their own skin. When they love their outfit, it shows in how they carry themselves — whether that’s raising their hand in class, joining a game at recess, or just walking into the lunchroom with a smile.
As parents, we spend so much energy on the logistics of school. But clothes? Clothes can be a little moment of joy, a reminder that they get to express themselves every single day.
Final Thought
Back-to-school is a fresh start — not just for kids, but for families. It’s a chance to set routines, start new chapters, and maybe even enjoy a little fashion along the way.
At Four Little Monkeys, I’ll always look for pieces that keep mornings easier, kids happier, and parents sane. Because when your child feels both comfortable and cool, they’re ready for whatever the school year throws at them.
Here’s to a year of learning, laughing, and a whole lot of recess.