I usually try and let my designs speak for themselves, but I found out so much useless trivia about Winnie-the-Pooh that I have to share it.

Edward "Winnie-the-Pooh" Bear: E. H. Shepard's drawings and Disney's design pose him as yellow and tubby, but in reality he was more of a tan, fairly blocky but-not-fat teddy bear. He'd be generic if it weren't for the tiny sweater.
Piglet: Wore a green jumper in the books. Also, take a look at the actual Piglet stuffed animal if you can. Is that even a pig?
Tigger: The most vintage toy looking of the toys. He was constantly quadrupedal in the book illustrations. I was gonna give him a ruff on his cheeks, but for some reason that removed the Tigger-y-ness. It's like part of his very character is being very uncatlike.
Eeyore: In the novels he had this sorta "miserable old bastard" thing going on, so he gets the patches his real life toy had before its refurbishing so he looks older and more pitiful. His tail nail is now a thumbtack.
Kanga and Roo: Mostly unchanged because the actual toys mostly look like that (except Roo? Roo was lost in the woods at some point.) The book makes Roo look like a squirrel, so here he is looking decidedly less squirrely. Kanga's pouch has a button because the book often has her "unbuttoning" her pouch for Roo, and it has a ruff to make it look more like an apron.
Rabbit: A regular cottontail rabbit with a slight yellowish tinge to his lighter hair. He's not a stuffed animal and he never was. He has a bowtie because he's so pompous, and is the most literate of everyone in the woods.
Owl: An ambiguous mix of different owls. He's not a stuffed animal either. He wears reading glasses (for irony's sake given he's basically illiterate) and, though it's not shown here, uses his talons for hands instead of his wings. He's very kind, but also way too proud for someone who can't read.

I was going to design Christopher Robin as well, but I couldn't bring myself to include him. Too many mixed feelings.
To understand why, read this: https://www.telegraph.co.uk/books/w.....stopher-robin/