I had a request months ago for ideas about outfits for watching grandkids. And I dropped the ball. In my defense, the three of us don’t have grandkids around, but I finally did a bunch of research and had us figure out some practical ideas.
Quote of the day: “The most important person is the one you are with in this moment.” Leo Tolstoy
There are many fabulous points I learned in my research with outfits for watching grandkids and a lot of it is dependent.
Dependent on the age of the grandkids.
Dependent on what you are doing with the grandkids.
It’s also dependent on so many other factors.
Yet when it comes down to it, outfits for watching the grandkids are not much different than many of the casual looks we wear for other occasions.
Insider details: I had to laugh reading a Facebook post in one of my midlife groups where a woman shared how tired she was after watching her grandkids, and how it reminds us why you have kids when you’re young. She also talked about staying in shape just to keep up with them.
I had the three of us think about different age groups of grandkids for our styling tactics. Yet there are a couple of similar points.
I’ve written about other casual yet stylish outfits in the past that could work as outfits for watching grandkids.

I spent much of my youth babysitting for kids of all ages. Remembering those days plus putting to use the information I gathered from friends, had me put together this outfit for these reasons:
What did I forget?


I Love the print mixing with this striped blouse and graphic tank top.
The secret with the “cardigan/blouse” is that I buttoned the last button in the button hole behind my body, This creates a wrap look so you get the advantage of sleeves but isn’t flowy in the front.




In Lesley’s words: “Having been a preschool teacher, mom and grandmother I’ve had my share of playtime with preschoolers. I’ve learned that you need to be comfortable, as fuss free as possible, and ready for anything. My loose tee can be styled a bit with a front knot and just for fun, I wrapped a stretch bracelet over dental elastic.
It is a nice touch if the bracelet was made by the charge of the day.
Having pockets on your pants is wonderful, but in case you don’t have pockets, a fun backpack is a good addition for carrying water, snacks, wipes, kleenex, bug spray, sunblock, bandaids, and of course wallet and phone.
Hats are a must for yourself and the little ones if you go outside, and if you are wearing one they will be more open to keeping theirs on. Comfy shoes with non-skid and tie are best so they can be used as a learning experience. If you have a bright fun pack you may be able to let one of your charges carry it and be uber cool.” (I call that beneficial slave labor, haha)


I love how Lesley thought of her tie shoes as a possible educational moment and the reasoning for this outfit for watching grandkids.



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As the oldest of the group, my mom got the job of styling her outfit, for older grandkids. Teenagers.
Now what do we know about teenagers? They probably don’t want to play with grandma as much as they would rather be on their devices or hang out with friends.
I do hear from friends that they try to dress up in a more modern way when they are watching their teenage grandkids. The kids think it’s “cool” when grandma’s “fit” doesn’t look frumpy.
Insider detail: The young kids call an outfit a fit. Use the term to be hip with the teenagers.
So that’s how Charlotte styled her look. Something she could hang around in with a modern vibe.


Since it’s doubtful that watching teenagers will include sitting and playing on the floor, my mom wore these ivory linen pants she created many years ago.
The sparkly white sneakers are footwear that would impress any young person.



I’d love to hear what other grandparents wear for a day with the youngins. Join in and I can add the ideas to this article.


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