Such a tricky tricky question!!!
I have been thinking about this for days too;-) Many hard choices to make
So here it goes :
pearl type - Tahitians are the ones that started my pearl obsession, blue akoyas are very close second favorites, I dont have budget for a strand of SOCs but the two mabes I have are my third favorites together with my gem luster WSSP drop. Luckily goldens dont work for my complexion and freshwater pearls are lovely but the easiest to give up for me.
pearl shape - I love baroques and circles in earrings and bracelets, for necklaces I prefer ovals or drops.
classics versus edgier pieces - My casual lifestyle favors light layering pieces as opposed to full strands of pearls, my lovely white akoya necklace from Takahashi is actually my least worn piece, I only had it once on last year. My dark Tahitian strand gets more wear but still not as much as tin cups, pendants, floating pearls...
favorite pieces versus most worn pieces - I love love LOVE my Tahitian Love necklace I know every pearl on it by heart as I slowly collected them all but again...it is my second least worn piece...The same goes for my silver blue akoya strand from Takahashi...I love looking at all the colors changing but I never really wear it...
Hmmm...my final 5...
Necklaces - Bliss rope is an easy choice, I wear ropes a lot and this one features so many of my favorite colored pearls.
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SOC mabe necklace, a very special pearl and sentimental necklace as I bought it with the money gifted by my Grandmother.
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Bracelet - “Tahitian harvest bracelet” different colors, different shapes, my most worn T barcelet together with a floating pearl on leather (my daily go-to) so I would keep my baroque akoya floating pearl which can be a necklace and a bracelet too.
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Earrings - I love love love pearls and gemstone combinations and I have quite a large earrings collection but only for one piece here I would with pistacchio, silver akoya and blue T combination.
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This was so so hard!!! I am happy I wont have to make this choice IRL ;-)))
Thinking about advice for new pearl collectors I would say try to see as many different pearls as you can and put them against your skin, pearls look different on pictures and then can either become alive when you wear them or you realize the color doesnt really work for you. This was a case for peacock Ts for me, I love looking at them but they never look as good as lighter pastel pearls on me. As you see more pearls IRL you will discover what your preferences are re-shapes, colors, size...
And go with recommended pearl sellers that have return policy because A) quality pearls can get pricey and you really should only get what you really love on you and B) it doesnt make sense to be stuck with “great deal pearls” that have bla luster and colors...