Five Degrees of Teddy (Loafers)

Meet Teddy. In timeless printed calf hair that gives everything in your wardrobe a kick of cool, and with a supremely comfortable wear-everywhere design, it’s basically the loafer of your dreams. So inspired are we by this new fellow in our style lives, that we can’t resist giving a shout-out to a few other beloved “Teddys,” just for fun.


Teddy Boys

A 1950s British subculture birthed in London and characterized by teenage boys who dressed in throwback styles—think tailored drape jackets and high-waisted trousers paired with creepers or Oxfords—and listened to American rock n’ roll. The moniker “teddy boy” was reportedly coined by the Daily Express in 1953 and the lifestyle was outlined in detail in the 1958 pulp novel aptly titled Teddy Boy by Ernest Ryman. And it wasn’t just for the boys; “teddy girls” (aka “Judies”) also had a trademark look, rocking pencil skirts, rolled jeans, flats and tailored blazers.

Teddy Bear

It was one Teddy that inspired the creation of another. After The Washington Post ran a hugely popular political cartoon about then-president Theodore “Teddy” Roosevelt’s experience with an actual bear on a hunting trip in 1902, Brooklyn candy shop owners Morris and Rose Mitchom decided to sew some plush velvet into the shape of a bear, dubbed it “Teddy’s bear” and displayed it in their store window. The stuffed bear was a sensation and thus the now-ubiquitous children’s toy was born.

Teddy lingerie

Once referred to as the “envelope chemise”, the teddy, a silky, slip-like undergarment meant to be worn in place of a bra and underwear (or over a bra) first hit the market in the roaring twenties.

“Ready Teddy”

A toe-tapping, hip-shaking rock n’ roll classic, the song originally written by Robert Blackwell and John Marascalco, has been covered by a host of musical legends from Little Richard to Buddy Holly to Elvis Presley, among others. In 1960 it even made it onto the big screen in Fellini’s La Dolce Vita.

“Teddy” by JD Salinger

With a documentary about the reclusive author’s life set to hit theaters this month, there is no better time to revisit some of his masterful stories. “Teddy” first appeared in a 1953 edition of The New Yorker and was then was reprinted in the collection Nine Stories. Salinger tells the tale of Teddy, an intellectually gifted child who meets a grad student and has a number of heavy discussions about spirituality, life and enlightenment with him. As controversial, (particularly because of the ending which we will not reveal here), as it is beloved, it’s a must-read for Salinger fans.