I don't know what it is about Jean that's so difficult, but my friend, who already has a long face naturally, also struggled to get his makeup right!
You've got some good contouring going on, so you've definitely gotten a good start. I'll reiterate what everyone else said about the eyeliner - try less of it, and instead of winging it out and up, maybe try extending the bottom line out a bit (not a whole lot! just a bit), keeping it mostly straight, and then have the top line curve DOWN to meet it. You'll want to have the bottom line start to straighten out around the middle of your eye. This way, it doesn't deviate from your waterline too much, but still subtracts some of the curve. I realize Jean's eye shape points up at the corners, but I feel like your natural eye shape is curved enough that simply having the bottom (straightened) line meet where the top lid line ends will give you enough curve to still be like Jean's. (I hope this is making sense!) But yeah, you can try that shape idea out and see if you like it. Regardless, I would make the eyeliner less thick all around.
Aside from the eyes, there are a few contouring spots I think you could emphasize more.
1) I see you contoured the sides of your nose bridge, but I think you could stand to do it even more and make your nose look taller. You might've done this and the lighting may be making it hard for me to tell, but I would extend the contouring all the way down to almost your nostril. I wouldn't just stop at the top/round part of the nose.
2) I do not see any contouring under your eyebrow/over your eyelids, so I would try that too. What a lot of people do is start the brush at the inner corner of your eyebrow, then arch it down to the outer corner of the eye. I can't quite explain WHY this helps, but for some reason it helps you look more masculine. XD
3) I think you did a bit of this, but maybe try more of it - Jean has a really long face, so the longer you can make yours look, the better. I would focus the jawline contouring on the area beside your chin where it's no longer the chin, but begins the jawline. Then you'll want to taper the contouring out gradually until you get to the corner of your jaw. So, biggest spot next to your chin, then tapering off until you reach the corner of your jaw. It should give your face a longer v-like look.
4) Also, don't forget to contour the v-shape on your neck as well!
Lastly, I agree on the eyebrows. You should make yours thicker at the base, tapering the thickness until you get to the arch of your eyebrow. I would add the thickness to the bottom side of your eyebrows to help "lower" the brows and thicken them at the same time.
Because I'm really bad at explaining things, I tried adding these make up tricks in Photoshop for you, haha. First one is an exaggeration of the color so you can actually see what I'm talking about; the second is a (hopefully) more realistic version of what it should look like.
I'm not an expert with Photoshop, but I hope it gives you an idea of what I mean at least! Of course, experiment and see what you like the most. When you actually have your Jean wig, that will make a huge difference as well, haha.