The NHL held its first Winter Classic in 2008 when the Buffalo Sabres hosted the Pittsburgh Penguins at the then Ralph Wilson Stadium in Orchard Park, New York. Since then the game has been contested 15 times.
One thing that comes with a Winter Classic is each team wearing a special jersey for the occasion. Some teams opt for a jersey with a newer touch on a throwback look, while others bring out a jersey that we’ve never seen before. Some looks are absolutely amazing and others just aren’t that good at all.
With plenty of jerseys to choose from, I went back and made a list of my ten favorite Winter Classic jerseys. Below are my favorite jerseys from the Winter Classic’s through the years!
10 – Boston Bruins – 2010

BOSTON – JANUARY 01: Marco Sturm #16 of the Boston Bruins celebrates scoring a goal to defeat the Philadelphia Flyers 2-1 in overtime during the 2010 Bridgestone Winter Classic at Fenway Park on January 1, 2010 in Boston, Massachusetts. (Photo by Jim McIsaac/Getty Images)
The Bruins have played in four Winter Classic games and I’ve been a fan of three of the jerseys they’ve worn. The only one not on this list is the 2016 game that was held at Gillette Stadium. I really liked the shade of yellow and the Spoked-B on this jersey. I also liked brown as the secondary color of the look.
9 – Toronto Maple Leafs – 2014

ANN ARBOR, MI – JANUARY 1: (EDITORIAL USE ONLY) Dion Phaneuf #3 of the Toronto Maple Leafs skates with the puck past goaltender Jonathan Bernier #45 of the Toronto Maple Leafs in a game against the Detroit Red Wings during the 2014 Bridgestone NHL Winter Classic on January 1, 2014 at Michigan Stadium in Ann Arbor, Michigan. (Photo by Jamie Sabau/Getty Images)
The 2014 Winter Classic was probably my favorite in terms of the jerseys overall (more to come on that with the next one of the list). The Maple Leafs blue and white look is really tough to mess up and they clearly didn’t with this one. I love the look of the Leaf on the crest and the striping on the arms and bottom of the jersey.