Thank you to Backcountry & ShopStyle for sponsoring this post.
I always know when the kids need a little fresh air—they’ll start going stir-crazy and then try to rile each other up. (And they’re really, really good at getting on each other’s nerves.) So I’ll tell them to grab their shoes and we’ll all head outside.
Ozzie’s at that age where a long hike is difficult—I can no longer carry him, and every little rock and leaf needs to be inspected by him as we walk by. So “exploring” the neighborhood is a great way for us to spend time outside together.
This year they’re both obsessed with gourds (not just “regular” pumpkins) and, fortunately for us, there’s an adorable little pumpkin patch right in our neighborhood. Walking there gives us a chance to get out and enjoy all the things I love about fall; the crisp air, the falling leaves, the gorgeous colors. The kids love exploring and I love them not fighting.
shirt dress (xs) | leggings (m) | cardigan (xs) | boots
Plaid Shirt Dress, Waterproof Boots & A Cozy Cardigan: My Go-To Outfit For Fall Family Outings
The outfit that always works for fall walks — especially if we’re going to be outside for a while — is leggings, an oversized cardigan, a plaid tunic/shirt/dress and warm waterproof boots. It’s a comfy combination that makes it easy to move around in and stay warm while Ozzie examines all of the rocks, leaves and dirt. (And first-time purchasers can take 15% off this entire outfit – and the rest of your Backcountry purchase – by using the code: THEMOMEDIT)
shirt dress | leggings | cardigan | boots
Warm, Waterproof Boots Are A Must-Have
The boots are key. If my feet aren’t warm and dry these walks won’t last long enough to get the kids’ energy out — I’ve made that mistake before. These Sperry Boots are perfect. They’re super-comfortable and warm (even without socks!) with a soft microfleece lining and waterproof rubber sole. I’ve been slipping these on daily, and they’re great in the rain — they’ll be spot-on for snowy weather later.
Can’t Go Wrong With A Cardigan For Layering
This Stoic cardigan is perfectly oversized for layering (and it’s on sale!). It drapes nicely over shirts, and the pockets don’t add extra bulk (I may or may not have hidden treats in those pockets for Ozzie). I just tie the cardigan around my waist if I get too hot chasing after the kiddos.
shirt dress | leggings | cardigan
A Plaid Shirt Dress Ties It All Together
Ooh and this plaid shirt dress? Has pockets. It’s all cotton and is perfect for layering under sweaters or over base layers. I’ve been wearing it as a shacket when I’m not wearing it as a dress, and it looks cute over graphic tees (like this “fearless feminist” one). It’s a bit longer in the back (which is good for curvier bodies!) so it covers everything. It does run big, though; I tried both the small and extra small, and went with the smaller size mainly because of my height (5’4″). It also didn’t shrink up a ton when I washed and dried it.

You know that gourd had to come home with us.
Shop Comfy Waterproof Boots
Shop Cozy Cardigans
Shop Fall Plaids
XOXO,
Scotti
A huge thank you to Backcountry & ShopStyle for sponsoring this post! I love all of the great finds that make spending time outside so much easier, especially with kids! Amy, thank you for your awesome photos! It’s always so fun working with you! And readers, thank YOU so much for your continued support. It is so very much appreciated!