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At the outside vs On the outside

at the outsideas the highest possible figure:

  • This woman is young, I suppose at the outside not thirty.

on the outside

1. on the outer surface:

  • Make sure the contents are clearly labeled on the outside.

2. (sl.) out of prison:

  • The funny thing is—on the outside, I was an honest man. I had to come to prison to be a crook.