Hi Sela!
Welcome to the Disney Parks Moms Panel! I'm from Texas and you're from Florida, so naturally we both understand how important personalization is. I fully subscribe to the theory of "If it's not moving, monogram it!" and thankfully when it comes to the most beloved and iconic Disney Theme Park souvinEAR, Mickey does too.
Sadly the
Minnie Mouse headbands that are sold all over Walt Disney World Resort are not able to be personalized. The material that covers the actual band is unable to be removed to fit in a sewing-style embroidery machine, and the ears cannot go in the machine as-is because the hard headband would prevent the machines needles from doing their magic.
You might find a few headbands that do have an extra touch of personalization, such as
these Graduation ears that include the graduation year on the actual band. I also purchased a limited edition 2018 commemorative ear band that is monogrammed with the year in the same fashion as the above graduation ears.
Something that I recently saw at Disneyland Resort in California was a display with non-ear articles of Disney clothing, like the
Spirit Jerseys and fleece blankets, that were personalized in-store after they were purchased. I'm sure the Disney World monogramming locations, which are Big Top Souvenirs and The Chapeau in Magic Kingdom Park, Mouse Gear in Epcot, The Dark Room in Disney's Hollywood Studios, and Discovery Trading Company in Disney's Animal Kingdom Park would be able to do the same.
We'll See You Real Soon, Sela!
~Kristen