Three Easy Holiday Outfits for Boys (that they’ll actually want to wear!)

One of my goals is to help make your whole family festive and fashionable and make your life just a wee bit easier this holiday season. Over the next week I’ll be featuring some easy holiday and winter looks for women and kids. Today we’re kicking it off with some holiday outfits for boys that they’ll actually want to wear.

Boys are a little trickier especially when it comes to holiday themed outfits. I’ll never forget the Christmas when our son Devon was around 10 years old and called his holiday outfits “dorkfits”. My mom’s heart got broken that year (but in his defense, they WERE pretty bad).

Back then I didn’t have J. Crew Factory and all of the stylish, non-dorkfit holiday options for boys. Their pieces for little guys are so dapper that my husband Craig wants adult versions of them. Lucky for him, J. Crew Factory has great holiday finds for the whole family, including dads. They also strike that perfect balance between quality and affordability that makes us moms really happy!

In my experience, I’ve found there are three types of holiday outfits for our kids –  a comfortable, casual look for activities like school parties, a dressier yet still comfortable version for occasions like family get togethers and a dressed up option for church and fancier events.

Let’s get started with a fun look that’s perfect for school.

Outfit #1 – School Holiday Party

Layer a Christmas themed long sleeved graphic tee under a buffalo check oxford and pair up with slim fit jeans that transition easily from party to playground.


Outfit #2 – Family Holiday Gathering

This one is great for family parties but would also work for a family photo shoot. Layer a plaid button down under an elbow patch crewneck sweater and pair with slim fit cords.


Outfit #3 – Dressed Up Events

I always resented buying dress clothes for my kids that only got worn one time. The pieces in this simple outfit – a white dress shirt, plaid tie, chino pants and belt can be reused throughout the year. Just swap out the tie.


Big thanks to J. Crew Factory for sponsoring this post and helping the whole family look our best this holiday season!