Just bought a little S hackamore for my TWH for trail riding. Does this fit look good? I’m used to fitting bits, but new to hackamores. This was her third ride with it and she really seems to like it, she’s responsive and relaxed, even more than with the mild bit I was using (Mullen mouth snaffle).
The fit looks good to me, but if it were my horse I’d put the cheek pieces up a hole. You may need to swap bridles to do so, as it looks like you ran out of hole real estate.
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I will be switching headstalls, I just need to take her regular one to get the cheeks shortened 
.
I will try it a little higher after I take care of that.
I think it looks good, I like the little S cheeks. Hopefully with a different headstall the browband won’t be so tight up on the ears.
I think the fit of the Little S itself looks great. I would definitely use shorter cheekpieces, and get a bigger browband. Here is what my mare’s setup looks like (but I think it may be one hole longer on the cheekpieces right now.) Those are pony size cheekpieces! This is a milder version of the Little S. The curb chain or curb strap cannot sit right behind the chin as it would on a bridle, because the noseband would be too low.
Updated pictures. I dug out another headstall and longer browband. (Note:I have WAY to much stuff 
). I have a one ear headstall, with a throatlatch, I used with the bit, but the cheekpieces are way too long. Once I get the fit right I’ll make a run to my Amish repair guy and get everything modified.
Just curious, what makes this a milder version?
The cheekpieces are not fixed in place so there is less poll pressure.
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That definitely looks more comfortable.
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I agree it looks better with adjustments. The benefits of being a tack hoarder.
I switched my OTTB to a hackamore this year due to being unable to find a bit he liked. He cannot handle the tongue pressure and ported bits didn’t help. I was honestly amazed by how much better he goes in hackamore. I went from being towed around in transitions due to him opening his mouth and pulling to being able to halt from sitting up and squeezing my shoulder blades together.
I decided to treat myself by buying a hackamore bridle that has an extra strap under jaw to provide a little more stability and my horse decided to rip his heel bulb nearly off his foot 
so will be a while before I get to test it out.
Thank you for the input everyone. All my other horses were both performance and trail horses and I have always used a bit. This is the first one I’ve had that I is 1) a trail horse only and 2) that I felt would really benefit from a hackamore so it’s new territory for me.
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