Bundle Up: 2025/2026 Gear Guide
- Stephanie Watson Yaeger
- Sep 3
- 3 min read
While we aren't quite ready for puffy jackets and wool hats, "Winter is coming!"
Each year it feels like if we don’t shop ahead of the season, we end up scrambling to find what we need. And when it comes to outdoor gear for kids, things sell out fast. We're sharing our chilly weather gear guide out early this year because we know it's a big investment to gear up for winter. Our family spreads out these purchases over time and we thought it might be helpful to have this resource early since many other families do as well. Hand-me-downs and second hand are great until the weatherproofing or warmth is no longer...there. We've learned that the hard way but there are ways to combat this, too!
Willowdale is grateful to partner with two of our favorite organizations that offer gear for year-round outdoor play and learning.
Oaki
Oaki offers everything from swim to snow and the Willowdale community gets 15% off all purchases with 5% going back to our organization which is pretty cool! Use code WILLOWDALE15 at checkout.
Outdoor School Shop
Willowdale families receive exclusive discounts and gear support through Outdoor School Shop! This is a private, curated shop, created just for our community. During checkout, use the code WILLOWDALE for 15% off your entire full-price order!
If you have any questions or need help choosing gear, please reach out to Alyssa at alyssa@outdoorschoolshop.com — she’s happy to assist.
Below are top picks, reminders and tips from our community that we've compiled over the years. We'd love to hear your favorites, too!
1-2-3 guide for gear
You may have heard this rule before, 1 - base layer, 2 - mid layer, 3 - outer layer (which includes accessories like hats, mittens and boots.) This can be applied to rainy days, snowy weather or frigid temps with no precipitation.
1. Base Layer
The layer closest to the skin keeps moisture away—sweat or dampness is what makes kids cold.
Best fabrics: wool, bamboo, or performance poly.
Brands we love: SmartWool. We have honestly tried others and feel like they don't last through the season.
Tip: Skip cotton—it holds moisture and will leave kids feeling damp.
2. Mid Layer
This layer insulates and traps heat. Think “cozy but breathable.”
Fleece or wool are tried-and-true favorites.
For budget-friendly options, fleece sweatpants and zip-ups from any store you typically shop, including second-hand, work great.
Add or remove this layer depending on the temperature.
3. Outer Layer
This layer protects against the elements—rain, snow, or wind.
Rainy days: Waterproof rain jackets + pants (we love Oaki Fleece-Lined Rain Pants for chilly, wet mornings).
Snowy days: Insulated snowsuits, bibs, or two-piece sets depending on preference. We love the Oaki Fleece-Lined Rain Pants for snow, too. I'm grabbing myself a pair this year (someone remind me.)
Chilly but dry days: A windbreaker, light jacket, or vest may be all you need.
Accessories That Make a Difference
Hats: Fleece or wool for dry days; waterproof + fleece-lined for snow.
Mittens/Gloves: Waterproof for rain/snow; knit or fleece for chilly days.
Socks: Wool is a game-changer—L.L. Bean and SmartWool both hold up well but IMO the bean socks are warmer.
Balaclavas: For those extra cold, windy winter days. We love TurtleFur.
Boots Families Recommend
Baby Bogs (lined) – Lightweight and warm for toddlers.
Kamik Waterbug 5 – Easy to pull on/off, durable enough for hand-me-downs.
SOREL Youth Snow Commander – Cozy, sturdy, and reliable in deep snow.
You can't go wrong with Bogs for any age.
I bought these Out N About Waterproof boots for myself last year and they are 10/10! I also recommend the Out N About Waterproof sneakers.
Gear Maintenance
If possible, try not to submerge your gear in the wash or dry it too often (this sounds ridiculous considering it's made for the harsh weather.) This will wear down the waterproof elements of your gear.
For re-waterproofing consider Nikwax - simply add it to your washer once a year depending on how often you use your gear.
Hang dry whenever possible.
Tears in gear will happen and thankfully we are back in the 90's (ha) and can just buy cool patches to repair them.
Choose "waterproof" over "water resistant."
Adjusting to chilly weather gear can be sensory overstimulation for kids (and us.) So many layers, so much bulkiness. Give your explorers, and yourself, time to adjust to the new routine of getting dressed for the cold and give yourselves extra time to get dressed prior to heading out.
When in doubt when asking "What should I wear today?" visit this resource from our friends at ODS!
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