Y'all just lit me up!
I am a self-professed pick whore. One of the greatest sources of pleasure in my life is a glass bowl I have in my practice area with a wad of picks. Some are favorites that I use, some I just like grabbing and remembering. When I was in college (read, broke), I'd go to the music store and buy a set of strings, and normally a half dozen different picks. Like everyone else, I started playing with Fender Mediums. Over time and lots of different pick playing, I chose the Tortex Blues in standard shape. We'll start there in the top center:
After many years of the blue tortex, I started trying to play jazz. I tried the stubbies for a bit, but came to play the purple sharps (top right) for years. Love those picks. I play with a self-taught hybrid style, using my middle, ring, and pinky fingers a lot, especially when chording. The smaller pick let me choke up a bit more while still being precise.
Next up are the Ultex, which I really dig for playing acoustic. Expensive, but they seem to last until you lose 'em.
A couple years ago, I went through a fit of the dropsies on stage. I convinced myself that it was due to the small purple picks. That got me searching for new picks again. What I found was that sometime in the past 10 years, Dunlop stopped polishing the edges of the tortex picks. I have a small stash of unused blue tortex standards from the early 90's that have very smooth rounded edges. The new ones look like they were punched and that's it - very ragged. However the Fender Premium Celluloid Heavies have a nice edge and I actually prefer the tone a bit over the Tortex. The pearl white ones have a slightly different flex than the other colors that I like. I know, I'm nuts.
Nex pick is one I'm pretty stoked about. This is a Fender Heavy celluloid that's in a very similar shape to the Tortex sharps. I'm liking this pick a lot. It has the feel of celluloid with a shape I'm really comfortable with. Too bad it only comes in "you'll never find it if you drop it" tortiseshell.
The next pick is a solid rosewood pick I bought at NAMM years ago. I gave one to a guitar teacher and he told me I ruined him for life. For playing chordal stuff on an archtop, this pick has no peer. Unfortunately, I only have one.
The final pick is the mack daddy. I found about 10 of these in a pawn shop in Melbourne, FL about 12 years ago. I bought them all, because they looked cool. However, they're my all-time favorite guitar pick. Slightly sharper than a standard Fender. It's a Pick Boy Heavy. Back then, I paid $.75/each. Later I found some similar ones in polka dots, and I bought every one. Only a few days ago I found a guitar store online in Japan that seems to sell them. I'm trying to find out how much it would cost to ship a gross of them to the US. I like them that much.
Sorry, I got sidetracked. To me, pick shape and thickness really do affect speed and tone. I can play with mediums, but I really prefer a heavier pick. Fender Heavies are about the lightest I care to play with. Blue Tortex are a bit stiffer and I like that size. The Stubbies feel a bit too thick to me.
For what it's worth, one of the best days I've had was spent with Bill and Clay Hullett. Bill was walking around NAMM looking at picks. Guitars were a consideration, but we were specifically looking at picks. Made me feel like I'm not quite so crazy.