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Toddler Boy Fall/Winter Clothes

Purple Star emoji 16 items
Keep your little guy warm and stylish with our Toddler Boy Fall & Winter Clothing Gift Guide. From cozy sweaters and puffer jackets to soft flannel sets and beanies, these picks are perfect for chilly adventures and everyday play.
Sections
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Pajamas

 
Katy Chilcoat profile picture
My absolute favorite pajamas for my toddler! They are super soft and cozy and come in so many patterns.
Sunrise Slopes Organic Cotton Two-Piece Pajamas - Mountain Blue
 
Katy Chilcoat profile picture
These are another fabric from Burts Bees Baby that I love. They have matching PJs for mom as well. My son and I rock these together all the time!
Honeysoft™ Mommy & Me Matching Thermal Lyocell Pajamas - Mountain Blue
 
Katy Chilcoat profile picture
I just bought these matching pajamas for my whole family! They are super cozy and comfy. Even my husband loves them!
Candy Cane Bears Matching Family Two-Piece Pajamas
 
Katy Chilcoat profile picture
My other favorite toddler pjs. They are SO soft and cozy.
Long Sleeve Pajamas in Jurassic
 
Katy Chilcoat profile picture
The cutest pjs for winter!
Kids & Baby Organic Brushed Cotton Holiday PJ Set | Gap

Shirts & Pants

 
Katy Chilcoat profile picture
The cutest sweatshirt! They have one that says “silly goose” I am going to buy for my toddler this winter.
Baby & Toddler Little Co. by Lauren Conrad Crew Pullover
 
Katy Chilcoat profile picture
This shirt with little corduroy pants for a Christmas service? Precious!
Baby & Toddler Little Co. by Lauren Conrad Long Sleeve Button-Down Overshirt
 
Katy Chilcoat profile picture
The cutest and softest thermal shirts for my little guy!
Long-Sleeve Thermal Knit T-Shirt for Toddler Boys | Old Navy
 
Katy Chilcoat profile picture
A pair of overalls is always going to be a must have for me. They are precious!
Baby & Toddler Little Co. by Lauren Conrad Corduroy Overalls
 
Katy Chilcoat profile picture
The cutest sweatsuit. Waffle knit - so super cozy!
babyGap Waffle-Knit Two-Piece Outfit Set | Gap Factory
 
Katy Chilcoat profile picture
I really love the Gap tshirts for my toddler. They are super soft and comfortable for him.
Baby & Toddler Heavyweight T-Shirt | Gap
 
Katy Chilcoat profile picture
I immediately added this to my cart.
Baby & Toddler Graphic Crewneck Sweater | Gap

Other Items

 
Katy Chilcoat profile picture
My toddler has this exact beanie and it is so cute on him. Keeps his head warm throughout the winter!
Carhartt Toddlers' Tonal Label Watch Hat
 
Katy Chilcoat profile picture
I didn't think about getting mittens for my toddler until I needed them last year, and these are a must have! Easy to put on and has an adjustable band to keep them on his hands.
ENBAOHUI Baby Waterproof Fleece Snow Mittens
 
Katy Chilcoat profile picture
The cutest shoes for Christmas time!
Double Secure-Strap Faux-Suede Sneakers for Toddler Boys | Old Navy
 
Katy Chilcoat profile picture
I am getting these for my toddler for Christmas - so cute!!
Kids' Grand Court 2000s Sneaker Toddler