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Purely my own opinion here. The logos I like the best are usually the simplest. Less is more. MLB cap logos that are mainly single letters or two transected or tandem letters. are the most effective. Fonts are free, there are millions of them, and intersecting them, making them 3D is easy even with the most basic graphics program.
Incorporating a smaller logo in the letters is pretty effective. The logo should be simple since it will be small and will look best if it is contained withing the boundaries of the letters. Take the Seattle Mariners cap logo as a good example. The compass is incorporated over the S but does not obstruct the S. The Miami Marlins is an example of bad logo. The little marlin device above and to the left of the M ruins the symmetry and since the logos in the game are 150x150 pixels it skews the size and alignment. It would probably look better without it. The Chicago Whales of the federal league and Anaheim Angels are other examples of small touches to letter logos that looked great.
Another effective tool is to use fills on the letters. The Arizona Diamondbacks and Washington Nationals alt "DC" logo are great examples.
Like I said, my own opinion only, but keep it simple. The New York Yankees have one of the simplest logos and uniforms in the MLB and they are always high on the list of the best.
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