What is the best way to achieve a more natural looking breast that jiggle when moving/jumping and feels more squishy? (photo)

Dear lunaluv601,First and foremost you need a breast lift.  You would then require either breast implants or fat transfer to replenish the lost volume in the upper breasts and create your cleavage.  The areolae would be reduced with the breast lift.  I think jiggly and squishy should be your least concern.  Good luck!

Hello and thank you for your question.  The
best advice you can receive is from an in-person consultation.  With that
being said, based on your photographs, the best shape and contour could be
achieved with an implant and a wise pattern breast lift. Your nipple sits
below the inframammary fold and without a lift in addition to the implant, this
will not have a natural shape.  A wise pattern lift with an implant can
result in a very nice shape if good technique is used.  The size,
profile, and shape of the implant is based on your desired breast
size/shape, your chest wall measurements, and soft tissue quality. 
This decision should be based on a detailed discussion with
equal input from both you and your surgeon.   Make sure you
specifically look at before and after pictures of real patients who have
had this surgery performed by your surgeon and evaluate their
results.   The most important aspect is to find a surgeon you are
comfortable with. I recommend that you seek consultation with a qualified
board-certified plastic surgeon who can evaluate you in person.
Best wishes and good luck.
Richard G. Reish, M.D.
Harvard-trained plastic surgeon