Classic Boys Clothes For Fall Weekends, Playdates, and More!

Casual & Classic Boys Clothes for Fall

Motherhood and Children

I’ve heard from so many of you that boys can be hard to shop for, especially when they just want to wear comfy outfits, so I am excited to share our classic boy clothes roundup for fall! Today we are sharing classic pieces that are comfortable, easy to mix and match, and transition well into winter. Good for school, weekend fun, and maybe even casual Christmas card photo options!

Click directly on the collage above to shop each item and scroll down for more cute fall finds for boys! 

J. Crew is one of my go-tos for well-made classics — and right now is a great time to stock up on fall basics because they are offering 40% off with code APLUS! Don’t miss these jeans (a must for weekends and playing in piles of leaves) or their long sleeve polos (a great price point and several color options.)

Boden is another favorite for classic boys clothes at affordable prices. They have so many cute tees and sweaters for boys. For younger boys, I love the sets at Smocked Auctions. Their fall collection is darling and so well priced! 

We have ideas for toddlers through elementary and many of these come in tween sizes as well. Click each item to see sizing! 

Tops and Tees:

White Turtleneck
To layer or wear alone!
Firetruck Turtleneck
Pair with overalls or the pants below! Several patterns to choose from, too.
Cute for dressier outfits!
Long Sleeve Pima Tee
The softest!
Puppy Tee
So so sweet!
Pumpkin Tee
Smocked Auctions has the cutest pumpkin-themed outfits!
Truck Tee
Lots of cute appliqué tees here!
Tools Tee
For the tool-obsessed!
Colorblock Tee
Easy stripes for mixing and matching!
Striped Tee
This one comes in several color ways!
Stripe Shirt
You can't go wrong with a classic rugby stripe!
Slim Stripe Polo
Love the green option, too!
Long Sleeve Polo
Under $40 and 40% off!
Lots of color options here!
active long-sleeve polo
He'll love these polos made with performance fabric! On sale!
long-sleeve pocket tee
Under $20 and on sale!



Cashmere Blend Crewneck
For the older boys! Great for the holiday season, too!
Football Sweater
Love this one for game day!
Puppy Sweater
For the puppy lover!
Monogrammed Half Zip
Personalize with their monogram or name!


Jackets and Vests:

Striped Vest
So cute with jeans, cords or khakis!
J.Crew Factory Vest
Perfect for casual or more dressy looks, too!
Quilted Coat
A favorite every year and 40% off right now!
Quilted Pullover
A great basic for fall and winter.



Airplane Set
These could be mixed and matched with other pieces, too.
Pumpkin Set
For your annual trip to the pumpkin patch!
Puppy Tee
Pair with the red pants next!
Red Striped Pants
So cute and so comfy!



Pull on for easy dressing!
Twill Faux Zip Pant
Flat front, elastic back and belt loops - perfect for younger boys!
Pull-on Pants
Available in both khakis and cords!
Twill Slim Pant
These come in lots of colors!
J.Crew Factory Pants
Love the pricepoint on these!
Pull-on Tech Pants
Click to see all of the color options.
Always a DoSayGive reader favorite.
J.Crew Cords
So many color options and 40% off!



L'amour Lace-Up Shoes
15% off with code DOSAYGIVEBTS15!
20% off right now! These are great for toddlers.
On Amazon Prime!
Velcro Sneakers
These come in a lighter color option, too!
Cowboy Boots
Every little boy needs these!
So cute!
Perfect for older boys!
New Balance Sneakers
A classic!

If you loved these classic boy clothes, don’t miss our fall favorites for girls’ post here

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