Well, here are DKC2/3-styled Winky and Expresso crates, along with updated versions of the DKC1 barrels, and some base sprites that may come in handy:
![Barrels, Crates, and a Sign.png](./download/file.php?id=1862&sid=a1e949254c39f6f0b32f1bcf136f2bf1)
- Barrels, Crates, and a Sign.png (11.14 KiB) Viewed 65182 times
A few things to keep in mind: Prerendered sprites are never uniform. Because they are based on a 3D model with a limitless amount of colors, trimming the color depth down to 16 nearly always results in shading that isn't perfectly smooth. Also, none of the prerendered sprites are ever symmetrical, even if the models they're based on are.
Going off of this information, I tweaked your sprite and wound up with this:
![tonberry2k's_winky_icon-modified_by_mattrizzle.png](./download/file.php?id=1863&sid=a1e949254c39f6f0b32f1bcf136f2bf1)
- tonberry2k's_winky_icon-modified_by_mattrizzle.png (834 Bytes) Viewed 65182 times
I also modified the eyes because they didn't look enough like Winky's. It's still far from finished, though.