In 1990, colleagues of Jerry Lauren had a Steiff bear made in his likeness for his birthday, down to the oxford shirt, tartan tie and cable-knit sweater, and a Western bear went to Ralph. In 1991 the Polo Bear arrived as a limited run of 200 teddies, and Ralph Lauren says they sold out in one weekend at the Madison Avenue flagship. The next year a bear wearing an American flag sweater was hand-knit onto a Polo sweater, and the Ralph Lauren bear sweater was born.

 

What I love is the joke at the center of it. The bear only ever wears the clothes the brand sells, so every new sweater is a tiny catalogue of the house: the blazer, the rugby stripe, the cable knit, the cap. Richard Tahsin, who drew the original bear art until 1996, told The Source that the brand has always used the same bear head he created, and only the outfits change.

 

The first grid is where I would start. The Polo Bear Cotton Crewneck in olive is the one most people picture, the bear in a cap and a yellow jacket. The Polo Bear Wool Sweater in grey is the warmer build for real winter. The two RLX pieces, the navy Performance Sweater and the V Neck Pullover with its cricket stripes, are the golf line's version, knit in technical yarns.

 

The rest of this grid is the current cotton shelf, and it is the biggest. The Polo Bear Flag Crewneck in deckwash white and the Traveler Bear Cotton Sweater in parchment cream are the two I would put next to the olive original, and the Polo Bear Cotton Crewneck in sporting royal is the bright one. The Polo Bear Hooded Sweater and the embroidered fleece hoodie in summer blue are the casual pair, and the collared cotton and linen jumper in parchment is the one I would wear to lunch. Then the sweatshirts: the Martini Bear fleece in black, the Traveler Bear fleece in grey and the fleeces in cruise navy and olive. A few here, like the Men's Cotton Knit Crewneck, the RLX Cotton-Blend sweater and the cruise fleeces, are cut in men's sizing, so go down a size if you want the fit closer.

 

A test I use: turn the sweater inside out. The bear is knit in intarsia, picture knitting where each color is worked from its own yarn, so the back of the motif should look tidy and every color block should be closed at the edges, not loose.

The bear went quiet for a while. GQ reports that Polo stopped making bear pieces in 2001, when the Steiff partnership ended, and brought the character back in 2013. By 2018 a Palace collaboration with a skateboarding bear in a blazer and tie had sold out before most people saw it, and that is roughly when the bear sweater stopped being a nostalgia buy and became a fashion one again.

 

This grid is the newer thinking. The Holiday Polo Bear Cotton Crewneck in black puts the bear in a white shirt and jeans, the dressiest of the set. The Polo Bear Oversize Cotton Sweater in pale blue is cut roomy on purpose, so take your usual size and let it slouch. The RLX Polo Bear Performance Polo Sweater adds a collar and a palm tree, the one I would wear with a pleated skirt. And the PRL x TÓPA Polo Bears Sweater comes from Ralph Lauren's Artist in Residence program, the fourth collaboration in it, launched in November 2025 with two bears instead of one.

 

The luxury end lives here too. Ralph Lauren Collection makes the bear in silk and in cashmere: the Polo Bear Silk Crewneck and the Summer Polo Bear Silk Crewneck in cream, and the Fall Polo Bear Cashmere Sweater in beige. The Pre-Fall Polo Bear Cashmere Sweater in portobello and the Holiday version in cream are the softest knits on the page, the Roll-Neck in Newport navy is the one for real cold, and the Martini Bear wool jumper in red puts the bear in a tuxedo with a drink. Purple Label's Silk-Linen Polo Bear Sweater is the most tailored bear of all, cut in men's sizing.

 

Styling note: a bear sweater wants one sharp thing beside it. A camel coat, straight dark jeans and a loafer, or a white collar showing at the neck. Pile on more prep and it tips into costume.

 

What I would skip: the oversize cut if you are petite and plan to tuck it. It is built to hang, and it looks best that way.

Robb Report calls choice Polo Bear sweaters some of the label's most collectible pieces, and a 1992 cotton-linen bear now resells as a vintage piece in its own right. You do not have to chase the originals to get the feeling, because the current range keeps returning to the same few ideas.

 

The flag bear is the first one. The navy and cream American Flag Bear Sweaters are the closest thing on the page to that 1992 original, the bear in a flag sweater on a plain ground. For texture, the Polo Bear wool and cashmere sweater is a cream half-zip with a fair isle band, the black wool-blend has two bears in tailoring, and the beige cotton and wool-blend puts the bear in a patterned sweater of his own.

 

The cotton ones are the year-round pieces: the cream intarsia with the bear in a brown jacket, the light blue with a navy blazer, the white with a striped top and a basket, the black with a flower in his hat, and the cream linen and cotton with the bear in a red POLO sweater, which is the one I would wear in April. The Polo Bear Crew Neck Sweater in grey and the Cotton Bear Long Sleeve Crew in pale blue round it out.

 

Two vintage flag bears sit here too, a red Polo Country USA flag knit and a red 1992 hand-knit flag bear, the closest you can get to the original. The grey Polo Bear Wool-Cashmere Sweater is the quiet one, and the Yankees Polo Bear puts him in a baseball uniform.

 

Then the sweatshirts, in black, cream, grey and blue, which are the softest way in and the easiest to wash.

 

What I would skip: buying two bears in the same color. Pick one navy, then let the next one be cream or olive.

The originals are not hard to find, they are hard to pick. Robb Report calls choice Polo Bear sweaters some of the label's most collectible pieces, and the resale market agrees with it.

 

Everything in this grid is secondhand. The 1992 Grandpa Bear in blue and the green RL'92 hand-knit are the early ones, the red 2001 hand-knit bear comes from the year Polo paused the character, and the 90s Preppy and Ski bears show how far the outfits went. Polo Sport's snowboard and equestrian bears are the sporty side of the decade, Polo Country's Nordic bear is the winter one, the ivory golf bear is the gentlest, and the basketball, golf and hockey sweatshirts are the easiest to wear every day.

 

Buying vintage, I check three things: the label, the cuffs and the intarsia. Ask for a photo of the inside of the motif and for measurements rather than trusting the size tag, and expect most of the 90s knits to be cut in men's sizing and roomy.

 

What I would skip: a vintage bear with a stretched or patched motif. The bear is the whole point, so it has to be intact.

Intarsia carries the yarn for each color behind the motif, so the bear panel is a little thicker and less stretchy than the rest of the sweater, and it is where a snag does the most damage. Wash it inside out, dry it flat, and keep it away from bag straps with buckles.

 

Cotton versions relax with wear and come back after washing, which is normal. The oversize cuts really are oversized. If you only buy one, make it a plain cotton crewneck in navy or cream with the bear front and center, the version that will still look right in ten years. The seasonal ones are a joy too, just buy them knowing they are for a season. If you want to keep browsing, I also put together Argyle sweater and Sweater Vests.