1. He tilted his hat rakishly to the side as he strolled down the street.
2. The actor flashed a rakishly charming smile at the audience.
3. The pirate captain wore his eyepatch rakishly over one eye.
4. The detective sauntered into the room, looking rakishly handsome in his trench coat.
5. She raised one eyebrow rakishly in response to his flirtatious comment.
6. The rake leaned against the wall, smoking a cigarette and grinning rakishly.
7. The young man drove his convertible with a rakishly carefree attitude.
8. The artist wore his beret rakishly tilted on his head as he painted.
9. The dashing gentleman winked rakishly at the ladies as he passed by.
10. The rogue flashed a rakish grin before disappearing into the night.