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.
8 – Detroit Red Wings – 2014
ANN ARBOR, MI – JANUARY 1: Drew Miller #20 of the Detroit Red Wings controls the puck as Paul Ranger #15 of the Toronto Maple Leafs defends during the 2014 Bridgestone NHL Winter Classic on January 1, 2014 at Michigan Stadium in Ann Arbor, Michigan. (Photo by Jamie Sabau/Getty Images)
Like I said, the 2014 Winter Classic was probably the best jersey wise. The winged wheel is another look that is impossible to mess up. I love the tan-ish shade the Wings chose to go with their classic red.
6 – Boston Bruins – 2023
BOSTON, MASSACHUSETTS – JANUARY 02: David Pastrnak #88 of the Boston Bruins warms up prior to a game against the Pittsburgh Penguins in the 2023 Discover NHL Winter Classic at Fenway Park on January 02, 2023 in Boston, Massachusetts. (Photo by Gregory Shamus/Getty Images)
The “meth bear” getting featured on the crest was long overdue! The Bruins nailed this look in my opinion. The crest was great, the stripes weren’t overpowering, and the color combo was terrific.
5 – Boston Bruins – 2019
Jan 1, 2019; South Bend, IN, USA; Boston Bruins right wing David Pastrnak (88) heads to the ice during the 2019 Winter Classic hockey game against the Chicago Blackhawks at Notre Dame Stadium. Mandatory Credit: Matt Cashore-USA TODAY Sports
The 2019 look was my favorite Bruins Winter Classic jersey. I loved the “B” on the crest, I loved the material used on the crest and numbers, and I loved the striping on the sleeves. The Bruins nailed this look in 2019.
4 – Montreal Canadiens – 2016
FOXBORO, MA – JANUARY 01: Brendan Gallagher #11 of the Montreal Canadiens celebrates after defeating the Boston Bruins during the 2016 Bridgestone NHL Winter Classic at Gillette Stadium on January 1, 2016 in Foxboro, Massachusetts. The Canadiens defeated the Bruins 5-1. (Photo by Maddie Meyer/Getty Images)
I hate to say anything good about the Montreal Canadiens…but this was sweet. The primary color being white, as well as the white “C” on the crest, with the blue stripe played so well off each other. This was an overall win for the Habs, especially their beatdown of the Bruins.
3 – Dallas Stars – 2020
DALLAS, TEXAS – JANUARY 01: Corey Perry #10 of the Dallas Stars leaves the game on a misconduct in the first period of the Bridgestone NHL Winter Classic against the Nashville Predators at Cotton Bowl on January 01, 2020 in Dallas, Texas. (Photo by Ronald Martinez/Getty Images)
The Dallas Stars green has always caught my eye and that didn’t change with this jersey. The big “D” on the crest and the word “Stars” written out across the front with the “A” as a star is a great design.
2 – Seattle Kraken – 2024
SEATTLE, WASHINGTON – JANUARY 01: Yanni Gourde #37 of the Seattle Kraken is congratulated by Joey Daccord #35 and Jamie Oleksiak #24 after scoring a goal against the Vegas Golden Knights at T-Mobile Park on January 01, 2024 in Seattle, Washington. (Photo by Steph Chambers/Getty Images)
The color combo…perfect. The crest…amazing. The Kraken killed it with this look. Keep these as an alternate forever. They are awesome.
1 – Pittsburgh Penguins – 2008
ORCHARD PARK, NY – JANUARY 01: Snow falls on Sidney Crosby #87 of the Pittsburgh Penguins during the NHL Winter Classic against the Buffalo Sabres at the Ralph Wilson Stadium on January 1, 2008 in Orchard Park, New York. The Penguins won the game 2-1 in a shoot out. (Photo by Dave Sandford/Getty Images)
This powder blues will forever be amazing. These looked so good on the ice and should make a return forever. Help me out here John Henry. Bring them back!
