Who else is nostalgic for fall?
The Cutest Retro-Modern Back-to-School Finds of the Season

Theresa Gonzalez is a writer based in Sonoma, CA and the author of Sunday Sews. She covers all things travel, design and food.
Oh the return to school and routine! There’s something so magical about a fresh box of sharpened pencils, brand-new shoes, and the feeling of a fresh start. Whether your kiddo is stepping into a classroom for the very first time or reuniting with old friends for a brand-new grade, back-to-school season is all about returning to the routines we love. From early bedtimes to after-school activities — and, of course, the shopping haul that brings it all together — we've curated the cutest retro-modern style, supplies, and gear to make this season's prep a breeze.
Scroll for the chic and affordable back to school supplies!

Rothy's
Rothy's The Kids Clog
The ultimate cozy-chic upgrade to everyday slip-ons. Lightweight, breathable, and machine-washable, these sustainable clogs offer all-day comfort for active kids without sacrificing an ounce of style.

Zappos
Vans Kids Classic Slip-On
Slip-ons are an absolute essential for smooth, hassle-free mornings. Timeless, durable, and effortlessly cool, these iconic checkered kicks are perfect for kids on the move—especially little ones who haven't quite mastered tying their shoes yet.

Gap
Gap Kids VintageSoft Relaxed Lace-Trim Zip Hoodie (Without Lace Trim)
It's almost hoodie season! Cozy, classic, and endlessly versatile, this zip-up hoodie is the ultimate layering piece for crisp morning commutes to school or laid-back weekend hangs. It brings a wonderfully soft, worn-in feel right from the first wear — making it a go-to staple for any cool-weather wardrobe.

Rifle Paper Co.
Rifle Paper Co. Mini Embroidered Journal
Inspire big imaginations with this beautifully crafted pocket journal. Featuring classroom-inspired illustrations, a charming embroidered detail, and plenty of blank pages, it’s a lovely space for creative doodles, daily thoughts, or quick notes.

Lalo
Lalo Bento Box
This one was great for summer camp, and I'm so excited to use it again this fall! Available in eight modern colorways, this durable bento box is a stylish essential for back-to-school and back-to-work routines alike. Built with non-toxic, BPA-free, food-grade silicone and stainless steel, it gives you complete peace of mind while keeping midday meals organized. Its sleek compartments ensure snacks stay fresh, tidy, and ready for hungry kids on the go.

Old Navy
Old Navy Crew Socks 3-Pack
Every back-to-school wardrobe needs a solid set of basics. Soft, stretchy, and built for everyday play, these classic crew socks keep little feet comfortable from morning recess to after-school sports.

Office Depot
Post-it Super Sticky Notes Bus Cabinet Pack, ($20/24 Pads)
Perfect for quick study reminders, book flagging, and homework organization — or for sneaking a cozy, handwritten love note into your child's lunchbox to brighten their afternoon!

Target
up&up Strawberry Journal Pouch Pink
Keep desk supplies and backpack essentials organized in sweet style. This versatile three-in-one pouch keeps pens, pencils, and small keepsakes neatly tucked away so nothing gets lost at the bottom of the bag. (Also available in botanical print)

Amazon
StiKiddo Personalized Name Stamp
Say goodbye to lost jackets and mixed-up water bottles! This waterproof, custom fabric-and-paper stamp makes labeling clothes, notebooks, and gear fast, easy, and smudge-free.

Amazon
YETI Rambler Jr. 12 oz Kids Bottle, with Straw Cap
Built to survive playground drops and busy school days, this insulated water bottle keeps drinks ice-cold from first bell to final dismissal. The leak-resistant straw cap makes hydration easy and spill-free all day long.

L.L. Bean
L.L.Bean Kids Junior Backpack
Perfectly sized for younger students, this classic pack blends rugged durability with smart organization. Featuring reflective details for added safety, room for a lunchbox, and handy stash pockets for tiny treasures, it’s built to last through every adventure.

Amazon
JBL Wireless On-Ear Kids Headphones
Whether they're focusing on interactive homework assignments or catching up on favorite shows during downtime, these comfortable wireless headphones deliver safe, volume-limited sound with total cord-free convenience.
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