If i had to rank out of experience...
Off the top of my head at the moment:
1. Winning Pro Fight (MS300) / Cleto Reyes Pro Fight / Cleto Reyes Safetec Pro Fight
then again, ^ those are all pro fight gloves. They should be easy to make a fist in right away.
I would even rate my limited experience with Amateur competition gloves (multi-layer padded ones of previous generation.. not today's IMF style amateur gloves) right under the pro fight gloves category... Everlast Amateurs (white knuckle from ~2006)... Title Masters Competition 16oz (white knuckle)
Training gloves:
2. Sabas TC / Everlast Elite
3. Winning trainers / Top Boxer Winning-inspired with Ortho
4. Everlast Powerlock
5. Sabas SuperSoft 2.0 / R2C C17 /Ringside IMF trainers (these were better fitting back in ~2006 though)
6. Cleto Reyes (thumb can be awkward at first)*
*It should be noted that Cleto Reyes took a while to break in. Once broken in, I would rate it among the top 3 or so.