Representations

Who is he?
An older male, of Caucasian ethnicity, from the look of his clothing and demeanor, he is probably homeless/very poor. He may just be trying to imitate this look though, as despite having patched up clothes, they are clean and in good condition. His shoes also look expensive and in relatively good condition.

What does he do?
He is a model or actor posing for a photograph to be taken, he probably usually plays/models characters of a certain type (old, haggard looking).

What's his story?
He started off as a homeless man, then was scouted to realistically play/model a homeless character, then made a career out of it.

Who is she?

She's an elderly female fashion designer, she's dressed incredibly flamboyantly/eccentrically, displaying her latest rang of clothes.

What does she do?
Makes and sells clothes she makes, if all of them are as disgusting as the ones she is wearing then she probably does so unsuccessfully.

What's her story?
She was always a bit odd, and she made her own clothes throughout her life, one day someone sarcastically suggested she sell them and she actually went through with it.

Who is he?

A stressed out, middle-aged man. Probably fairly well off but doesn't enjoy the money much because he is always stressing out.

What does he do?
Sells designer sunglasses to tourists/rich customers at his shop that has a pretentious name.

What's his story? 
Grew up in a wealthy family, never had to work for anything as a child and coasted his way through education getting mediocre qualifications, and borrowing money off his parents to set up his shop.