What lift and breast implant shape and size would you recommend to get the look i want - dense, side boob, cleavage? (Photos)

I would suggest meeting with a board certified plastic surgeon in your area and discussing a breast augmentation and lift. I do not recommend going for a DDD because of the heavy weight on your now stretched and thinned tissue.

It is certainly possible to get a more full upper pole by utilizing breast implants. The type, style, and size of implant would need to be chosen based on what is called tissue based planning. This technique requires choosing the correct implant based on your chest wall "base width" amongst other measurements. Based on these measurements, I would choose a moderate plus or high profile implant. A high profile implant will give you more upper pole fullness, while the moderate plus implant will give you more of a side profile.
In terms of the lift, I feel as if your lower pole will need significant reshaping. You will likely need a small horizontal scar along with the vertical scar, which would be more of a Wise pattern or "keyhole" lift.
In terms of the look you are going for, I think it is always important to remember that the goal is to improve the look of your breasts by correcting the specific anatomic problems, not to give you someone else's breasts. I think the upper pole fullness is achievable, but correcting the lateral breast curve is notoriously hard in breast rejuvenation.

Based on your photos, you need a procedure that will address the horizontal and vertical excess breast skin and tissue. This can only be achieved with an "anchor" or "inverted-T" final scar.