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Clothing design for anthros/furries?

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ɹǝʇlᴉℲ
I usually envision furries has having prehensile tails, easily able to maneuver it through a hole in clothing. Sure, maybe one's tail would need to be brushed a little after getting dressed, but nothing unmanageable. Kind of like brushing your hair after putting on a t-shirt.

As for your options, I'd go with the 2nd. When I checked to see if velcro would stick to my cat, it didn't. That one might be less problematic than you think.
 

Foxridley

A fox named Ridley
I once spent some time pondering how overalls might work for a tailed character. Best I could come up with was something along the lines of a large fly with buttons or snaps. It could be opened up wide when putting it on, so an anthro wouldn't need much fine motor control in their tail.
 
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