Just a few ideas:
1. You might try encouraging her to go braless around the house. Once she gets accustomed to that, you might suggest she try coming to the door for deliveries, fetching the Post (getting the mail), or a friendly dare to retrieve something from your car sans bra.
2. Once she gets used to that, you might convince her to go braless elsewhere (darkly-lit restaurants, a night-time drive around town).
3. Always have her bring a light shawl or something to cover up with in case she feels too exposed. Make it a game, always with a safe way out (cover up with jackets or scarf).
For what it's worth mentioning, I've tried all of these with my wife, and failed miserably. I could seldom convince her to try. She tried a few ideas once with no one around, then adamantly refused to ever do it again.
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