I wanted to redo this series of characters in a tiny bit more detail and I wanted to use an outlined style this time. I'm happy with the outcome.
There is a whole background story around these guys that my wife is currently writing. I've had offers from 2 different companies to make these into a series of toys, but nothing has materialized as of yet.
Will keep you updated.

The story so far:

Simon Kendal Sheldonthorpe & his buddies are at the country club golfing (playing tennis, whathaveyou) & says:
"Hey fellas, don't forget about my party tonight"
"Okay Shell, we won't miss it!" Shell leads the group on the
way to the clubhouse. Niles hangs back a second to speak to Amanda "Bunny" Bananahammer.
"So Niles, will I see you Friday night at the mixer?"
"Well, Bunny, I did have another soiree to attend, but I'll see if I could make an appearance for your sake."
"Don't you do me any favours Niles Fontainbleu."

Back in the clubhouse, over highballs & cigars, Simon politely excuses himself from the table because at precisely 3:45 pm every Tuesday, he calls his mother before her afternoon tea. In his absence, Niles starts scheming.
Pretty typical for Niles. After all, his whole life has been a scandal. Starting with his birth!
You see, his mother, Helga, was very in love with her husband, Aloisius but Aloisius worked incredibly hard at his law firm. He was the youngest lawyer to ever make partner at Gibson Gibson & Tallywhacker. When they were first married, Helga gave up her promising career as a slalam skier to focus on her marriage & starting a family. She & Aloisius were very carefree. But Aloisius was in law school then, and they were living comfortably in his parents guest house. When Helga became pregnant with their first son, Hector, Aloisius became obsessed with seeing to his future. Aloisius graduated law school a whole semester early & passed his bar on the first try! He soon had a job at Gibson & Gibson, (before they partnered with Tallywhacker). He worked such long hours that Helga soon became very lonely. She attended a book club once a week &, it's rumoured, became a little too social with one of the male members. Nine months later Niles was born, looking nothing quite like his father, or brother. Niles was always getting into trouble, ever since he was a small child. And the trouble grew with him until his college days when he began drinking, womanizing, & gambling. In fact, he depleted his trust fund so rapidly that his father, no longer having any faith at all in him, wrote him out of his will. This prompted a huge feud & in the end, Niles started using his mother's maiden name, Fountainbleu. But I digress...
Niles, in Simon's absence, says to his good friends all sitting at their usual table,
"You'll never believe who I just ran into on the grounds!"
Before anyone could begin to answer, Niles exclaims,
"Bunny!" (A simultaneous cringe from the crowd.)
"She says there's a mixer Friday night!"
"But that's the same night as Shell's party!" cried Frederick.
"I know, but come on, there will be women at the mixer. You know damn well that Shell is too shy to invite a girl!"
"Actually," started a muffled voice, until Arlington removed his hat, "that's not entirely a bad idea" Mr. Hive continued on,
"We would never miss Shell's party, but what if we stopped by the mixer before hand. Brought some girls back to his place with us, as a surprise."
"Ya know, that's not half bad," added Edward, "You know he
hasn't so much as crossed paths with a girl since Belinda."
Belinda Jane Thortenwhistle. Formerly, Belinda Jane Frostensmythe, and for a brief period immediately following her marriage to proctologist, Dr. Davidson Grey Thortenwhistle, she was Belinda Jane Frostensmythe-Thortenwhistle. But it was too much for her delicate wrist to take signing that way on every
credit card receipt, and there were a lot of those. She had, six years ago, been briefly engaged to Simon. She was the only woman he wasn't shy around. Having known her since prep school through her two brothers, or possibly only one and a half, he thought of her more as a sister at first. An annoyance really. But he sometimes even played along & went to her tea parties, until one day, he realised he liked going. He no longer shrugged off the invitation like her brothers used to, but then again, he noticed one day, her brothers were no longer invited & they were both far too old for tea parties...