toddler boy fall outfit

The Cutest Toddler Boy Capsule Wardrobe For Fall

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Though it may seem a little silly to some, a capsule wardrobe for an adult is no different than a capsule wardrobe for a baby/toddler. You have your key essential pieces that can be mixed and matched with everything in your closet. This reduces impulse buys and last-minute stressful shopping trips because you find out you need something that you don’t have!

Shortly after finding out I was having a boy, I started freaking out because I didn’t know about boy fashion. What looks good? What’s cool in the guy world? Yes, birth and labor fears did come later. 😉

Then, I realized, there’s nothing to be scared of (for both things). Dressing a boy is not all that different than how I would dress me! With a more masculine spin of course. Motorcycle jackets? Yep. Boots? Yep. Skinny jeans, hats, and layers? Yep, yep, and yep!

I don’t know about you, but I love to shop more for my kid than I even do for me! I didn’t know that was possible. Man, this is what people must mean when they say motherhood changes you 😉

My tee | Will’s tee

Usually, in a capsule wardrobe, you spend more because you’re buying less, but when it comes to clothes for babies and toddlers I am in favor of investing at the moment because…kids haha. I’m okay with going cheaper in these areas. Gucci shoes? Fuhgeddaboutit. I’m linking to some similar items that are around $20 or less.

Toddler Boy Fall Capsule Wardrobe


green jacket
As you ladies know, a green jacket is the epitome of fall! Though the anorak type might be a bit too girly for boys, bombers or canvas style jackets work great for them.

toddler boy fall outfit

Will’s jacket (thrifted) | cute options here and here

motorcycle jacket
What could be cuter than a kid in a motorcycle jacket? Go ahead and try to think. Waiting! I love how cute and tough little guys look in these.

matching mother and son fall outfit

Will’s jacket (got it on sale) | cute options here & here

Related: Family Fall Weekend

denim jacket
A great choice for casual looks or when you need an extra fall layer.

Will’s (thrifted) | cute options here, here, and here

I for one love cardigans on guys and though I’m still trying to get my husband to wear one, I do have control over what my toddler wears. 😉 Still deciding on a few though!

cute options here, here, and here

Not a total necessity, but it works great as a layering piece either over sweaters or under jackets!


plaid button-down
What says fall more than a plaid shirt? Not much! Well, maybe everyone posting their #PSL on the gram, but that’s about it! This can be worn by itself, open over a tee, layered under a moto jacket, or tied around the waist!

cute options here, here, & here

It’s #sweaterweather! Let’s see how many fall cliches I can fit into this post!
Don’t really need much of an explanation on how to wear a sweater- looks great worn by itself with jeans or with casual joggers for a cool contrast.

Will’s sweater | cute options here & here

basic tee
No wardrobe is complete without the basic tees. They can go under cardigans, jackets, or be layered under an open button-down. Or look really good on their own because hello, #basicisawesome!

Will’s tees | cute options here & here


I think joggers are sometimes cooler than normal pants. They just have that cool edge! Whether the joggers are a jogger style chino or cool sweatpants, They can be worn casually with a tee and they look oh so cool when you throw a moto jacket over it!

toddler boy fall outfit

Will’s (thrifted) | cute options here, here, & here

Related: Family Fall Day at the Apple Orchard

skinny/straight jeans
Thankfully, boys don’t need tons of bottoms. A couple of styles will do just fine and you can just wear them again and again. Skinny/straight jeans will be your go-to staple! I like a slimmer leg but I’m not into Jonas Brother skinny though!

Will’s jeans | cute options here & here


Boots look great with both skinny jeans and joggers and well, go with everything!

toddler boy fall outfit

will’s boots | cute options here & here

Little kids don’t need a lot of shoes (unlike me 😉 ) so boots and sneakers will do just fine. It doesn’t matter which pair, but try to get shoes in both black & brown so you have something to go with everything!

cute options here, and here


Why go basic with socks when you can add a fun little punch?

Will’s socks | cute options here & here

A kid has got to stay warm, right? So why not stay warm in a cool hat that adds some street cred?!

toddler boy fall outfit

Will’s hat | cute options here & here

So European! Plus, it’s practical too, so what’s not to love?

toddler boy fall outfit

will’s scarf | cute options here, here, here, & here

I can usually find what I’m looking for at my local consignment stores, but Amazon and H&M are always winners, as well as Zara and Target! Or you can always follow the links in this post. But I haven’t tried everything, so read reviews first!

If you want more inspiration, keep reading this next post on How to Create a Stylish Toddler Wardrobe!

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Toddler Boy Fall Capsule Wardrobe


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.