Oi Polloi

In Praise of... Christopher Robin

Published: Fri Sep 04 2020

There's a lot of under-appreciated (and occasionally misunderstood) people, places and inanimate objects out there. With these articles - we like to reset the balance a bit.

For this one, Tayler Willson waxes lyrical about the stripped-back stylings of Christopher Robin...

After our recent dive into the sartorial expertise of the young professional grass Tintin, we’ve become increasingly obsessed with unearthing more well-dressed fashionistas from the world of illustration. From TJ Detweiller’s laid back look of Converse, bomber and snapback in Recess, to Dimitri from Anastasia’s neatly-tailored suit and unforgiving comb over, we’ve found it’s often the case that penned characters remain in the same rig for the majority of their time. Christopher Robin, though — a name you may know from A.A Milne’s Winnie-the-Pooh books and poems — is a shining exception.

For a boy drawn to be so timid and soft, the sheer fact he was best friends with an anthropomorphic teddy bear speaks volumes on his tenacity. Based in the fictional forest of Hundred Acre Wood, Christopher Robin is both pal and owner of Winnie-the-Pooh (the aforementioned anthropomorphic teddy bear), as well as with other inhabitants like Eeyore, Piglet, and Tigger, plus others. While embarking on daily adventures that often centered around the bear’s addiction to honey or cheering up a sad donkey, one intriguing tale that was never told was how Christopher Robin himself came to be the proprietor of such an excellent sartorial arsenal.


With a wardrobe for every season, his summer rigs were arguably way ahead of the times. Lightweight, open-collared polo shirts were paired with boxy cotton shorts, neutral socks and a pair of pumps and would always give off an indisputable Riviera vibe. Distinctly different, yet inexplicably just as eye-catching, was his summer school uniform. Charcoal grey shorts and socks and dark chocolate brogues, all sat below a loose-fitting off-white Oxford shirt paired with a dark brown sweater vest with a neat beige trim — completed with a neat cap for good measure.

Despite his penchant for dressing like a cultural boat-owning tastemaker or a new wave librarian, his autumn and winter collections must take centre stage. Roll-necks were the go-to in the colder months, garments that were never left alone with lightweight jackets, corduroy blazers and button-up cardigans for company. From mustards, browns and caramels, his roster of roll-necks were about as autumnal as they come and expertly seasonal. Such was the heavy rainfall in Hundred Acre Wood, big coats and waterproofs played an integral part too. Vibrant Guy Cotten-like sailing jackets would regularly make an appearance (usually alongside a similar blue iteration from Winnie-the-Pooh), while more subtle button-up pieces alongside patterned scarves, hats and gloves were often seen as well.

While the wardrobe of Christopher Robin was ultimately down to the ideas of A.A Milne, the character himself was in truth based entirely on the author’s real life son Christopher Robin Milne. Despite images of his young son dressing mainly like a Victorian ghost, the fact A.A Milne had other ideas in his fiction shows a sense of style on his part. And even if you aren’t a fan of the young lad’s rigs, the fact he’s sticking with short shorts all year round, must be a point of appreciation at the very least and certainly something Oi Polloi can endorse.