Rainbow Rocks 10th Anniversary - Let's celebrate the 10th anniversary of Rainbow Rocks with an art event! Here
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Background Pony #265A
Short tail hair (or even docked tails) would be more likely in the military, where ease of maintenance is a big issue.
 
Don’t forget when Twilight used her tail as a slide/ramp for Spike.
Diamond Dust
The End wasn't The End - Found a new home after the great exodus of 2012

Easy answer. Ponies have a set hair length naturally. If a pony has their mane or tail cut, it immediately grows back. This was shown in gen 1.
Background Pony #327F
@HJSDGCE:
 
Implying that one cannot just make a good swing with a knife
Prof.NightJack
Equality - In our state, we do not stand out.
The End wasn't The End - Found a new home after the great exodus of 2012

Gizmonics Scientist
I don’t understand what your getting that, I see it like humans with hair styles, they go with what they like, nothing more to it.
Sixtyfour215
Thread Starter - Fire Emblem Stuff
The End wasn't The End - Found a new home after the great exodus of 2012

Well AJ uses her tail to use a lasso with, so there’s an advantage to that.
 
Also, removing tl:dr tag since this is only two very short paragraphs.
Sjogre
The End wasn't The End - Found a new home after the great exodus of 2012

Long tails are more useful. Real horses use them to shoo away flies, both of them have used them as whips, and Applejack has used hers as a limb.