Best Cold Weather Finds for Toddler Boys

I’ve been doing some shopping for Miles for the upcoming fall/winter and have found some great picks I figured I’d round them up. Some links are affiliate links.

Cold Weather Shoes

Looking for some cold weather boots is what sent me down this rabbit hole so let’s start with shoes.

Boots: (in order left to right, top to bottom)

  • L.L. Bean Rain Boots – Currently 20% off with code KIDS20 (through 8/30)
  • Bogs Pull-On Boots – A wide variety of the popular Bogs boots are on sale right now (certain colors and patterns). Also try the code BOGS123 as it may still be active for an additional 10% off.
  • L.L. Bean Winter Boots – We all know L.L. Bean knows how to make good outdoor gear. Right now they have 20% off all kids using KIDS20 so a great time to stock up.
  • Bogs Insulated Rain Boot – If you want more of a rain boot style but with warmth, these are currently on sale. Again, try the code BOGS123 as it may still be active for an additional 10% off.

Slip-Ons: (in order left to right, top to bottom)

H&M Sneakers – Good quality everyday sneaker for under $30

Old Navy Leather Slip Ons – RUN, these are on sale for only $18 PLUS an additional 30% off. They also come in canvas if you don’t want leather.

H&M Waterproof High Tops – Ok these are just cute but I love that they are waterproof because I have had too many instances of Miles running to puddles in improper outdoor shoes.

Teva Ember Moc – These are on sale right now in limited sizes/colors but Teva makes great shoes so wanted to include them in the roundup. These are super nice nylon slip-on shoes with a sturdy rubber sole.

L.L. Bean Wicked Good Slipper – The classic L.L. Bean Slipper for little ones! Miles has a pair of slippers he LOVES.

Bog Slip-on Shoe– If you like the look of the Ember Moc but they don’t have your size this is another good option. Moisture-wicking, easy on, and machine-washable. I just got a pair for Miles, they seem too easy!


I love checking H&M every season for clothing. They can be a little overwhelming because they have SO MUCH IN STOCK. But, overall I’ve gotten really good quality pieces that hold up really well. I highlighted a few of my favorite finds below. They have some great sweater and pants options this year between $12-$19.

L.L. Bean

Currently Kids stuff is 20% off using the code KIDS20 until 8/30 so it’s an amazing time to stock up on any winter gear you need.


Primary has a handful of things on sale right now. Even their regularly priced stuff is a good deal.

Old Navy

They currently have some great staples on big sale and a TON of stuff is an additional 30% off.

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