Back to School: Outfits for Toddler Boys

Back to School is here! I’m bias as a mom of two boys but dressing them is the cutest! I’m sharing my favorite outfits for toddler boys!

There is nothing as exciting as shopping for new school supplies & new clothes!

At least that’s my personal opinion 😛

I can remember every year, school shopping was one of my favorite things to do with my mom. The sheer excitement of deciding what color jelly pens or what new pair of jeans I could pick out!

Now it’s my turn to have the fun with Oliver. It was even a little surreal picking up his school supplies because that means he’s another year older. Cue the ugly crying!

Every summer, Oliver seems to grow two sizes more, so recycling last years clothes isn’t an option right now. And don’t get my started on Elliott. That little chunk grows an inch every day!

So I put together some of my favorite clothing items for Back to School shopping. And of course my favorite styles for those little toddler boys!

First Day of School

Is there anything more adorable than dressing your toddler for the first day of school?! I love something comfy and classy for them to meet their teachers and have some fun on the playground!

Pocket Crewneck Sweater // Perfect Jersey sweater that will keep them warm in the classroom.
Skinny Jeans // I’m a sucker for Oliver in skinny jeans. H&M has some adorable styles this year including these in a Light Denim Wash!
Olive Green Backpack // Simple and stylish! Olive Green is my color this year 😉 It looks even cuter with Oliver!
6-pack Low Cut Socks // Can anyone else agree that there is a Sock Thief in their house?! These low cut socks are perfect for gym shoes or dress shoes.
Marcellus Oxfords // I just about fell out of my chair when I saw these. Cat & Jack always wins in my book, but these Oxfords are on my shopping list!

Gym Day

Boys are fun, but they do get sweaty! I love these styles for Gym Days at school. Perfect to stay active and super comfy!

5-pack Cotton Shirts // H&M is killing it with the fun fashions! These cotton shirts are perfect and comfy for toddlers to wear to the park or gym day at school.
Mickey Mouse Baseball Cap // Every little boy loves Mickey right?! This hat is adorable and super basic for them to wear with anything.
Moto Joggers // I personally cannot pull off the Moto Jogger, but I know Oliver loves this style. They’re super comfy and they aren’t baggy at his ankles. Love these for the playground too!
Adidas Sneakers // Finding shoes that can withstand Oliver’s running around is a must. These Adidas Sneakers are adorable and of course, I love the matching color green! 😛

Holiday Party

One of the most exciting times with the school year, planning the Holiday party! This outfit is adorable and will look so dashing on any toddler boy!

V-Neck Cardigan // The most adorable and softest V-neck cardigan! Any little boy would look so darling in this!
Plaid Tie // This is perfect for any holiday party or for church on Christmas Eve! The plaid is so festive and adorable.
White Button Down Shirt // I am a huge Cat & Jack fan at Target. This white button down is perfect with any pant or with khaki shorts for warmer weather!
Toddler Khaki Chino // I didn’t realize J.Crew had children’s wear until I found these! They’re so adorable and they have an internal elastic waistband!
Cat & Jack Brown Belt// Essential for any wardrobe. This brown belt can go with dress pants or jeans!
Brown Slip-On Loafer // I’m pretty frugal when it comes to shoes for Oliver and Elliott because they only last one season. But these slip-on loafers are adorable and will be perfect for any holiday and special event!

Springtime Outfit

Once the weather starts warming up, we transition to Spring clothes. These items are perfect for staying warm with the changing temperatures.

Vineyard Vines Baseball Cap // I am a sucker for Vineyard Vines. They have the cutest t-shirts and this navy blue baseball hat is perfect for spring!
Stripe Sweatshirt // With the transition to Spring, you’ll want to have them stay warm with the cooler temps until later in the afternoon. This stripe sweater is adorable and perfect for the chilly mornings but a heatwave in the afternoon for recess!
Drawstring Cargo Shorts // These shorts are a great fabric, sturdy enough for recess and the drawstring gives them some flexibility around the waist.
Dinosaur Backpack // Oliver is obsessed with dinosaurs. This printed dinosaur backpack from Nordstrom is adorable!
Cat & Jack Sneakers // Can you tell I love Cat & Jack?! These navy blue velcro sneakers are amazing for Oliver to slip on himself!

Winter Essentials

Having a winter jacket is a must in Michigan! These are just a few essentials we use for the school year to keep Oliver warm at recess.

GAP ColdControl Puffer Jacket // Staying warm will be essential for Michigan winters. Side note: I asked the preschool tour guide if they do recess outside every day. She said absolutely! So this puffer jacket will be a MUST for us!
Cable Knit Thermal Hat // I basically chose this because look how adorable it is! Why would you NOT choose this hat?! I may want to wear it myself, and it’s perfect to cover Oliver’s ears.
Thermal Underwear // Having thermal underwear will be necessary for the snow days! This performance stretch set will be perfect for keeping them warm at the bus stop.
SnowBank Waterproof Boots // The slip on boots are so frustrating because it’s so hard to pull them on and off! I love these laced snow boots and it will keep their socks from getting wet!
Green Cargo Pant // Thermal underwear will go great under these. They’re warm enough for recess outside, and keeps them comfy while they’re inside.