I always keep Sugar's hair in a topknot. I know what you mean about that ponytail headache but it doesn't seem to bother him so maybe dogs are just different. I did buy a pack of those cheap plastic barrettes (shaped like ducks, flowers, etc.) and the intention was I would use those for nighttime since they aren't as tight. Haven't been too good with the follow through though.
I redo Sugar's topknot every morning and give him a little scalp massage also.
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"If you have men who will exclude any of God’s creatures from the shelter of compassion and pity, you will have men who will deal likewise with their fellow men." — St. Francis of Assisi, 1181-1226