1. without care or concern

- carelessly raised the children's hopes without thinking of their possible disappointment

Similar word(s): heedlessly

2. without caution or prudence

- one unfortunately sees historic features carelessly lost when estates fall into unsympathetic hands

Similar word(s): incautiously

3. in a rakish manner

Similar word(s): raffishly, rakishly

Sentences with carelessly as an adverb:

- The papers were carelessly strewn on the table.

- Distracted by the salesperson, he carelessly read the contract.