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Winter Classic jersey rankings: Where do the 2023 Bruins, Penguins land on all-time list?

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The Winter Classic is an annual outdoor hockey game with an annual timeline for fan arguments.

They begin when the venue is announced — “Fenway Park … again?” — and continue when the participants are revealed — “The Pittsburgh Penguins … again?”

But the arguments reach their apex when the uniforms for the teams are revealed, as teams and the NHL’s retail partners attempt to create a look that’s an instant classic for the Classic.

Many times, they succeed. “I tend to like Winter Classic jerseys more than I dislike them,” said Chris Smith, founder and editor of the hockey uniform news and analysis site Icethetics.com. “Believe it or not, a list of my least favorite ones is actually harder to make.”

Harder, but not impossible. With the 14th NHL Winter Classic scheduled for Jan. 2 between the Penguins and the Boston Bruins, here is our official ranking of all 28 jerseys from the league’s foremost outdoor event, with some expert analysis from Smith and fellow sports gear guru Chris Creamer of Sportslogos.net.

But to find out the best Winter Classic jersey, we must begin with the worst …

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