3 Ways to Make Getting Your Kids To Dress Up for The Holidays A Little Easier

three ways to make getting them dressed easier

Outfit Details: 

Me: Madewell Sweater, Dark Wash Jeans, Similar Leather Ankle Boots
B: Plaid Flannel Shirt, Gray Pants, Similar Lace Up Boots
Fos: Dog Sweater, Olive Green Jeans, Vans Hi-Top Sneakers
San: Blue Bear Sweater, Blue Jeans, Freshly Picked Moccasins


If my kids had it their way, they’d wear a free t-shirt and basketball shorts every day. Seriously. Last week, we were off of school and every single day they wore basketball shorts and flip flops. Getting them to dress up is like pulling teeth sometimes.

Sometimes I’m fine with the super casual clothes, but most times I like them to look a little nicer. And the holidays present lots of opportunities to look a little (or lot) nicer.

Today I’m teaming up with Nordstrom today to share three ways I get them to dress a little nicer, especially this time of year.

dressing your kids up for the holidays
dressing your boys up for the holidays
velcro hi top vans
dressing up a bit for the holidays
getting ready for the holidays
reading christmas books


  1. Choose super comfortable options. My boys hate stiff shirts, or anything that might be remotely scratchy. They’ll rip it off in two seconds. So I’ve learned to look at material, and I know which brands are guaranteed to be comfy. Tucker + Tate at Nordstrom is always one of my go-to’s because they have sturdy pieces, great prices, and they’re always comfy.
  2. Compromise a little. I would always choose a plaid or crisp striped button down, but a graphic sweater with a dog or a bear is something they’ll be much more likely to put on, and so many of them are super cute and not tacky. I draw the line at characters — no mickey mouse or darth vader on our nice clothes!
  3. Let them help pick. When they feel like they have control over the choice, they’re much more willing to wear whatever it is. But to keep them from going too wild with their choices, I usually pick out 3-4 and let them choose between those. Works every time!

Any other tips?? I’d love to hear!


Thank you to Nordstrom for partnering on this post

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