I find when I ride bareback it really helps to get the feel for a longer leg and have noticed on video I can keep my heels down better without an actual stirrup. With that said, my heels have never drug in the ground. I rode Welsh cobs for the better part of a decade, ride a fjord now and am 5’6 with longer legs than torso so I generally have had to bring my lower leg up more for cues as well.
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I’ve always noticed I ride better without stirrups.
I’m 5’2" and actually used to riding larger horses but my current guy is only 15 hands. I do think I’m wanting to use my heel too much, drawing it up even more. So lots to work on, as always!
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Ugh this is me too, but even worse I actively brace against my stirrups. It’s a really hard habit to change, I’ve been working on it for a few years with little improvement 
Now I’m mostly just trying to focus on not nagging and getting my horse more in front of the leg because that’s when like you said they just get shortened and drawn up. I also struggle with straight elbows, I think I’m finally starting to make a bit of progress there.
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I’m seeing a pushing leg position or a gripping leg position. Is your horse a push ride? Do you feel like you’re holding onto him with your legs to stay with him?
If you feel like you ride better bareback it could be a gripping leg. Test yourself by riding without stirrups (or bareback) and actively point your toes at the ground (don’t just not lift your toes to get the heels down position, actively point your toes like a ballet dancer). Pointing your toes activates the opposing muscles to the gripping muscles, and you will find yourself feeling very unstable if you’re usually gripping.
I used to grip with my legs in canter and I rode bareback and practiced pointing my toes to learn to balance with a long, relaxed leg. Any time I feel my heel coming up I’ll drop my stirrups and walk with toes pointed at the ground for a minute or two to help release the muscles shortening my leg.
Your stirrups may well be too long if you feel your leg position is good at the walk and you lose it at faster gaits. My younger horse has a much bigger trot than my older horse and I have to ride with stirrups a hole shorter than I feel comfortable with at the walk so that can maintain a good leg position in trot. I had to go up two holes at first and then worked my way back down one hole. I still feel they’re short at times, and also long at times (like a massive trot forward along a country road mid endurance ride 
).
Younger horse can also be a push ride at times and I have to be careful not to get stuck in pushing all the time. I have several exercises that help me get better responses and a lighter leg.
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@Lunabear1988 have you ever been evaluated for pelvic floor dysfunction? Tightness there can lock you up and make coming down through your legs, out of the hips very difficult. That ability to drop through your hips is where good leg position starts
A urogynecologist is who evaluates and treats this condition… With your EDS it might be worth a consult.
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Your horse is cute and I think you two are a very nice pair!
I don’t know anything about EDS, but my first instinct was to say, 1) ride without stirrups more while focusing on a “long leg” and 2) if you’re more comfortable in your jumping saddle, ride in that. I rode dressage in my jumping saddle for years when I was eventing (BN and N) and had a very tight budget 
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after looking at your photos, i google-imaged dressage photos specifically to see how people held their hands and i see that your straight arms are a different look. Though some of the photos i saw (hundreds) did show riders with their hands down by the pommel.
Now, i am far from being an expert, but seems to me, that when your hands are low like that and your elbows not bent, the lever effect might make you lean forward and that might make your legs also move back…? So…leverage-y speaking, if you were to break that cycle anywhere it could change all three things. Straighten your back, try to be plumb shoulders through hips…
Or lift your hands up? Hope my ignorance doesn’t offend you. People on here get so touchy when someone ‘lower’ offers advice!!
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Yes I think that’s the root of it. I’m used to riding more TB types. But my guy now is more chill. He can be in front of the leg but you have to be serious about from the get go. And I really need to think about using my leg differently… I want to use my heel more than my calf. Arg!
It’s so frustrating when we know what to do better body does something else lol
Yeah as I mentioned in my post that is an ongoing thing too. That’s actually getting a lot better although most of these photos are a little bit older, at least a few months old. Part of it for me is riding a green horse and thinking I needed a longer rein. Now that I’ve shortened my rein it’s much easier to keep a bent elbow. I’ll see if I can find any new photos but I don’t have many opportunities to get photos of me riding.
I don’t think I’ll ever have picture perfect elbows because of my height and size and everything. But yes it certainly could be better and there’s some multiple position issues. Regardless it is frustrating. Because I know what to do I just can’t get my body to do it!
Yes he is a push ride which is definitely part of it! And I go to using my heel too much instead of my calf … And I need to be better about backing it up with the whip.
I actually don’t have any problems losing my stirrups though in any gaits. I will try different things without stirrups though.
i have some ‘things’ too. just different from yours is all.
pretty sure everyone has their bugaboos?
lately i feel like my back isn’t straight.
and i can’t seem to post and tap my heels against my horse at the same time.
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I have not… Worth a consultation. Sometimes my hips do cramp up and I have to stand up to release. Mostly in wide twist saddles. This saddle doesn’t go that at least…
Thank you!! He is a good baby. I definitely will start to work more with no stirrups.i tried finding lunge lessons ( I love those) but can’t find anyone with a suitable horse currently. But I can do a little with my young horse.
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Yeah my elbows are my longest running frustration. I used to ride hunter under saddle on the AQHA circuit (years ago) and I swear the straight elbows were encouraged.
I do break the habit but it pops up- especially on a green horse. I do know how to break that habit easier though. The leg stuff is new.
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Haha mine is a TB - a very lazy one! Here is a really extreme example of my problems (in dressage saddle):
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I do not know if this will help you.
I have MS, and my riding teacher had continually gotten after me for my lower leg. Nothing she suggested and nothing I tried worked.
Then I was reading “Riding and Jumping” by Harry Chamberlin. On page 28 this caught my notice–"Normally the knee joints are almost completely relaxed. They are not entirely limp, but work sufficiently to keep the lower legs in place. (my emphasis) IF THE (knee) JOINTS ARE ABSOLUTELY LIMP, THE LOWER LEG SLIPS TOO FAR TO THE REAR, WHICH PERMITS THE HEELS TO COME UP, THE BUTTOCKS TO SLIDE FORWARD, AND THE STRENGTH AND BALANCE OF THE WHOLE SEAT TO BE DESTROYED.
My problem ended up that I was trying to keep my knee joints too relaxed. Once I fixed my knees and lower legs we could proceed to my other multiple problems with my seat.
I had to go to an anatomical drawing of the thigh. Since gripping with the knees is out, letting the knees float over the saddle is out, and bringing up the heel is out, that left me with the Rectus Femoris muscle, the one on the front of the thigh. IF I keep some tension in this muscle my lower leg problems simply disappear and my riding teacher stops yelling at me about my lower leg. I only use a light tension on this thigh muscle, too much tension will send my feet forward and my butt slams down into the saddle. It is a balancing act.
I have MS, my proprioceptive sense is horrible and I often cannot feel it when my body gets out of kilter. When I concentrate on keeping a light tension on my Rectus Femoris muscle everything improves, I feel more secure in the saddle and my lower legs STOP swinging back. My ankles are not as supple as they used to be, but when my lower leg is properly forward my heels look a lot lower than they would normally.
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Ha ha I have some that are worse for sure!! Especially going over poles
I’ll look up this muscle and give it a try. I definitely feel like my lower body is working too hard. Not what we are going for at all. But definitely might be me just concentrating on the wrong muscles.
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I have to thank everyone, posting photos of yourself riding with your apparent riding flaws can be scary. But everyone has been helpful with constructive criticism so thank you!
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