Know yourself, know your audience and know your lifeguards. Don't wear anything you feel too self conscious in at the pool, that you suspect will draw the wrong kind of attention to you or will get you asked to leave by the lifeguard.
Little girls and teenage boys can make hurtful comments, parents become protective, gay men may start following you around and the lifeguard may publicly blow his whistle and send you home.
If everyone is wearing knee length shorts in the pool then for your first time in Lycra wearing square cuts isn't a bad idea. If that works out ok then push the envelope and try some 2" classic racing speedos, after all 2 " speedos are sportswear. Until there is a scattering of men wearing 2" speedos in your local pool don't try pushing for a 1" bikini, you'll be on your own, appear to be trying too hard and fingers may begin to point in your direction.
The beach is different, there is space, you can get away from the crowds and set up your own location with your own rules. Strip down to you 1" bikini; swim in the sea, walk about on the sand or sunbathe on your towel. Passers by will see you, most will walk on by but a few will claim their spots close to you, some may choose to wear brief swimsuits too but all have chosen to accept you as you are.
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