“Why can I see your underwear, son?” D.C. Fire Chief Kenneth Ellerbee asked a young man, with short dreadlocks, who shrugged, laughed and explained that he had forgotten his belt.

Minutes earlier, D.C. Council member Yvette Alexander (D – Ward 7), asked a similar question as the young man and a half-dozen friends pressed her to help them find jobs.

The exchanges took place in August at the Deanwood Recreation Center during National Night Out, the annual community event that is touted as a way for law enforcement and residents nationwide to help reclaim the streets from criminals.

It was 90 degrees and humid as a live, free-style rap show served as background noise. Police officers and federal agents talked to each other at booths meant to entice the general public.

Meanwhile, little boys tossed free Frisbees they had collected as giveaways, while dozens waited in line for snow cones.

And in the center of the street, young men in their early 20s, with NBA ball caps, fresh sneakers waited for advice about how to enter the work world.

The adults offered one place to start: pull up your pants.

“Oh, you’ve got Ralph Lauren,” Alexander told one of the young men. “I guess you want to show that off.”

What would happen, she asked, if they dressed like that and a nice, white lady walked by. “Do you think she might cross the street?” Alexander said.

“Probably run across the street,” one young man countered.

All laughed. But the point was made: first impressions count. Alexander pointed out a couple of men in the room—this reporter included—who had career jobs.

But the 21-year-old with the dreadlocks wanted specifics about how he could get a job. He turned to Ellerbee, who told them education was the key. He referred the young man—who had briefly attended Prince George’s Community College—to try the University of the District of Columbia.

“That’s where I started,” Ellerbee said.