Try a small range
Buy a few clearly different picks rather than a large bag of one unfamiliar model. Keep one flexible example, one medium-feeling option and one noticeably rigid pick. Printed thickness is useful for identifying them, but material and shape also affect how much they bend. Two picks with the same number need not feel identical.
Use the same short chord pattern and single-note passage for each. Keep your grip relaxed and expose a similar amount of the tip. If one pick seems to catch repeatedly, first notice whether you are presenting more of its edge to the string. A technique change can make a larger difference than moving to the next thickness.
The tip and grip serve different jobs
A pointed tip can feel precise for individual notes, while a rounded edge presents a different contact surface. Neither requires you to use a particular style of music. Compare how easily you can alternate between strumming and picking a single string, especially if both occur in the songs you practice.
Grip texture, holes and larger bodies are worth considering when the pick rotates unexpectedly. Check that the surface feels comfortable without requiring a tighter pinch. A thick pick that stays oriented may be useful, but a heavily textured one can feel distracting. Keep the experiment about what your hand actually does rather than what a famous player uses.
Listen and feel separately
Play unplugged for a moment to hear the contact noise, then use your normal amplified or recorded sound. The acoustic click of the pick may be prominent in the room but less important in the final sound. If you record an acoustic guitar, try the same microphone position when comparing picks so that the difference is meaningful.
Notice fatigue as well as tone. If your hand starts gripping harder as a pick becomes slippery, stop and reset rather than completing a long comparison with increasing tension. Short, repeatable trials are easier to interpret than an hour of switching between unfamiliar shapes.
Keep the useful ones identifiable
After a few sessions, retain two or three options with distinct purposes and note their model or color. A small compartment in the case prevents the comparison set from disappearing. Inspect worn tips occasionally; a rough or uneven edge can make an old favorite behave unlike a new replacement.
There is no need to choose a permanent winner. A flexible pick for one strumming part and a firmer pick for another task can coexist. The useful outcome is knowing why you reach for each one.
