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That might work, I'm not sure. We odered some pretty cheap ones already personalized from kustomkoozies.com
That is a cute idea! I wonder if the iron on transfer would melt the koozie though? Silk screening might work better?
I decorated Koozie's for my friend's bachelorette party, but I didn't try to do a print on it. I hot glued the ribbon onto the top of the coozies and made bows and attached them to the front. I stamped tags with "All You Need is Love" or "Kiss and Tell" on the front, then wrote "Friend's name, bachelorette party, date." I attached the tags on the bow.
They stayed on during the whole bachelorette party, while getting ready the morning of the wedding and during the reception (us bridesmaid broke them out shortly into the night).

This is the best picture I could find! I wish I had a close-up to send you!!!
If the material won't melt you can absolutely iron on a transfer. If it melts you have to screen print. That's what happened to my oot bags so I learned how to screen print!
@LadyGoodman - Those are f'ing adorable!!!
@LoriLori - How do you screenprint?
The ones we got are not like the ones in LadyGoodman's picture, they're the thin, collapsible ones......I don't think they'd melt but I guess I never thought about that. I will have to try it out this weekend see. Thanks ladies!
I used Photo EZ - http://ezscreenprint.com/ it was really easy!
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I ordered some plain black collapsible koozies online and was wondering if anyone has tried decorating them on their own? I was thinking we could design something and print it on an iron on transfer sheet or something, and iron it on? What do you think?