To celebrate the holiday season, Ralph Lauren dropped three new limited-production watches featuring the brand’s iconic Polo Bear motif.

Each shows the bear in a different style of clothing — one nods to the tony Bedford, with a tweed jacket and boots; one embodies casual Americana with a flag sweater and denim; one is all dressed up in a double breasted tuxedo.

They show off the full spectrum of Ralph Lauren style, and with a bit of tongue-in-cheek attitude, too.

The watches are all technically identical, with only the lacquer dials varying. They are all 42mm across, 10.7mm thick, and made of stainless steel.

I particularly like the placement of the crown at two o’clock and the use of wire lugs, giving the cases some old-school charm.

Additionally, both the Bedford Bear and Denim Flag Bear watches come with two straps that you are meant to be able to mix and match, should you choose.

While some of the diehard watch nerds reading this might be thinking “Wait, why are we reading about teddy bear watches on HODINKEE?,” I beg you to stick with me on this one.

The Polo Bear has real history and is something worth knowing about.

It dates back to 1991, when Ralph Lauren employees supposedly bought both Ralph and his brother Jerry Lauren teddy bears as gifts — only the bears were dressed up like their bosses.

The two men were charmed and thought it would be fun to sell a limited run of the bears at the Ralph Lauren Mansion on Madison Avenue.

They sold out quickly, and then the Polo Bear started making its way onto everything from sweaters, sweatshirts, and other Ralph Lauren goods.

Now, nearly 29 years later, there are collectors dedicated to just Polo Bear merch, hunting Ebay, flea markets, and estate sales for rare variations.

Sometimes the Polo Bear is surfing, and sometimes he is relaxing, but he is always decked out in head-to-toe Ralph Lauren.

It is a perfect example of Ralph Lauren’s ethos of doing serious things without taking himself too seriously. — Bloomberg

The basics

Brand        : Ralph Lauren

Model        : Tuxedo Bear, Bedford  Bear, Denim Flag  Bear

Diametre        : 42mm

Thickness        : 10.7mm

Case material    : Stainless steel

Dial colour        : Off white lacquer with bear motif

Indexes        : Arabic numerals

Lume        : None

Water resistance    : 50m

Strap/bracelet    : Black alligator  strap (Tuxedo Bear), tan leather strap and tie silk strap (Bedford Bear), denim strap and tan leather strap (Denim Flag Bear)

The movement

Calibre        : RL200

Functions        : Hours, minutes,            seconds

Power reserve    : 38 hours

Winding        : Automatic

Frequency        : 4 Hz (28,800 vph)

Jewels        : 26

Additional details: Swiss made

Pricing and availability

Price        : US$2,150 (RM8,729) (Tuxedo Bear), US$1,950 (Bedford Bear and Denim Flag Bear)

Availability    : Immediately

This article was originally published on Hodinkee.