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What weight of leather are you trying to embroider on? If it is garment weight I have done it many times. However I would never attempt to embroider through a leather halter. I make custom leather halters and the thickness and density would make me afraid of damaging my embroidery machine. Just my 2 cents.

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Tips on sewing with leather, I use  a thin backing to protect the hoop so no marks get left on the front side of the leather as hoop can cause marks. make sure its tight but not too tight. I also have used adhesive to stabilize the fabric.   I also use a regular needle for suede or lighter leathers.

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One issue is the needle but others are keeping the halter still while you embroider. Also the needle penetrations are going to weaken the leather since leather is cut by the needle unlike fabric where the needle separates the fibres when it passes through. What you might want to do is make embroidery onto a fabric that will then be wrapped around the halter and secured by velco. Then the name/embroidery can be changed from halter to halter, bridle to bridle. If you still want to try doing it directly, work the design center out and since the halters are VERY thick leather you might want a titanium needle for strength. Also be aware that because of the thickness the needle may have a problem clearing before the machine tries to move..hence breaking needles. Let me know what you end up deciding.

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