He thinks to encourage the other man's discretion but for what purpose? Anyone overhearing them wouldn't believe what he's hinting at anyway so they already have that protection.

"I meant I pictured you in some place even less reputable, maybe in the middle of a brawl. That's the impression you give off with your clothing choices, anyway." Sasuke raises a hand to signal a waitress, lifting two fingers. "She'll bring a pint over for you too."