Can you wear pearls everyday? YES! I like how pearls accentuate any outfit. I've considered myself a "pearl girl" since high school.

So it should come as no surprise that I would endorse the wearing of pearls with flannel or other casual wear. Pearls will take any casual outfit to another level.
My red and black flannel shirt is one of my favorites to lounge in. It sometimes doubles as a jacket. But when I add pearls, it becomes flannel-chic! Flannel-chic...that could become a thing! Haha!
Pajama Party Pearls
Several years ago, I coordinated a pajama party for our church's women's weekend celebration. We had rented space at a lodge in the Pocono Mountains and the event was awesome! All the women attendees dressed up in their favorite and most comfortable pajamas.
My pajamas were a little on the dressy side, so you know I just had to wear pearls, right?
I slayed!
Conclusion
So, I don't think there is a wrong time to wear pearls. The only decision to make is size and number of strands!
What I'm Wearing In Top Photo:
Pearls: Thrift shop
Levi's Flannel Shirt: BonTon Stores
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