Ranking the Top 10 NHL Winter Classic Jerseys
The 2023 Winter Classic drops the puck at Fenway Park in Boston on January 2, and with it, we'll see the Pittsburgh Penguins and Boston Bruins duke it out in some sweet new jerseys.
This will be the 14th NHL Winter Classic, which means there are a pretty good number of jerseys to think about, and when I'm thinking about them, I'm thinking about which one was the best. I did this with Penguins and Bruins outdoor game jerseys earlier this season when their jerseys for this game were unveiled, but now I'm widening the focus to all the sweaters from past and imminent Winter Classics alike.
There are throwbacks, and some of those throwbacks have come full circle and become the regular jersey for some teams. And then there are the "fauxbacks" that look like something from a former era but are something new meant to look old again and ideally look really good.
Obviously, the rankings will be my opinion, and you're going to have to deal with it, but I'll be making my choices based on aesthetic quality, style, nostalgia, and just a general gut feeling.
Will these rankings be consistent with my previous set? Probably not! These are very tangible things, and I am unassailable in my takes, but if you somehow disagree with them, light me up in the comments. You'll still be wrong according to me, but that's OK; I still want to hear it.
I'm picking 10 of them, so we'll start from the back and work to the front.
10. Dallas Stars (2020)
When the Winter Classic went to Texas in 2020, the host Dallas Stars stepped up their fashion game quite nicely for the first Winter Classic in the deep South.
Admittedly, the Stars don't have a wealth of history to draw from for inspiration for a throwback-style jersey while they've been in Texas, so they went deep into the heart of Dallas hockey history for inspiration.
The crest is a nod to the Dallas Texans from the 1940s in the USHL, and the jersey has an outline of Texas on the sleeve with the capital "D" in the middle of it. Most of all, it's green as heck. The Stars have saved their own jersey history for their Reverse Retro looks the past two seasons, so that's fine. Paying homage to the history of hockey in Dallas was a super call, and it helps that the Texans had a pretty great look back in the day.
I'll ignore the khaki pants for this since all I care about is the jersey itself, but just know I don't like the pants at all. Whether it makes them look more like cowboys or not doesn't matter—they weren't good.
The jersey, though? That's really good.
9. St. Louis Blues (2017)
The St. Louis Blues are a two-time Winter Classic participant, but when they made their debut hosting the event in 2017, they went back in time to nail a great look.
The Blues used their inaugural 1967 jerseys as the inspiration for their first time in the Winter Classic, and it made a ton of sense to do that, given the team was celebrating its 50th anniversary of entering the NHL. With such a no-brainer decision, it worked perfectly.
Most importantly, the look is extremely blue, but it's that slightly lighter shade of blue that makes it special and also makes it just different enough from its original look to make it its own special thing. There's something about that particular color that makes it stand out so strongly. Whether it's the hue or makes you think it's actually something from way back in the day, it's just a real handsome jersey.
You know it's a really good look when a team hangs onto it as an alternate jersey, which is exactly what the Blues did with this one, as they continue to use it now years later. When teams roll out something that looks, feels, and acts vintage but technically isn't vintage, that's the real sweet spot for what clubs should do to dress it up for the Winter Classic.
8. Chicago Blackhawks (2009)
The Chicago Blackhawks have been in a lot of Winter Classic games. A lot. They've had many opportunities to show off something old, something new, something borrowed, and something askew, but it was in their first appearance in the New Year's Day spectacle when they got it absolutely right.
When the Hawks hit the ice at Wrigley Field against their hated rival Detroit Red Wings, they did so with nearly identical throwbacks to what they wore from 1935-37 with a more updated (and slightly less offensive) crest, and those jerseys are just about as clean and perfect as they get.
The Blackhawks actually wearing black can sometimes look not-so-great (see: 2019 Winter Classic), so tapping into their history made all the sense in the world for their first time outdoors. Even Chicago's 6-4 loss to Detroit didn't dampen the memory of these jerseys because it stuck around as an alternate for a couple of more seasons, including during their run to their first Stanley Cup win since 1961 in the 2009-10 season.
Chicago would land in three more Winter Classic games in 2015, 2017 and 2019, but they wouldn't look as good as they did in 2009.
7. Pittsburgh Penguins (2011)
The 2011 Winter Classic had many flaws to it, but one of them was not how the Pittsburgh Penguins and Washington Capitals looked on the ice, and the Penguins brought the heat.
Pittsburgh used its logo from 1968 and put it on the front of these dark blue beauties, something they hadn't done before. The skating penguin donning a scarf flowing in the wind is an elite logo. The baby blue and white stripes are outstanding on the navy-blue background, and the unique-looking numbers with drop shadow stand out.
I love this jersey, and I think it's perfect and probably should be higher on this list, full admission.
However, like I said when I ranked out the Pens and Bruins outdoor game jerseys, this look, for me, is forever haunted because of what happened to Sidney Crosby in that game.
The hit from David Steckel that nearly turned his career upside down is forever attached to this jersey. It probably doesn't help the Capitals also won the 2011 Winter Classic 3-1, but the "spookiness penalty" I've assessed to this one knocks it down the list.
6. Philadelphia Flyers (2012)
When the Philadelphia Flyers get a jersey right, they absolutely nail it, and they nailed it for their 2012 Winter Classic look.
First off, it's a lot of orange, just the way it should be. It's the classic Flyers logo for the crest, as you'd expect, but when you add the faux-vintage laces, it classes it up a bit. But it's the captain and alternate captain patches that make it extra unique.
The white keystone design with a black "C" or "A" in the middle of it is the perfect nod to the state of Pennsylvania (it's the Keystone State, after all) and when it's the Flyers facing the New York Rangers, being as Philly (or Pennsylvanian) as possible is mandatory.
It's a jersey that looks like one they've worn in the past, but it's wholly original in its creation which helps make it stand out even more. You add in the fact that Jaromír Jágr was on the Flyers at the time and got to wear this beauty as well, and you all should feel lucky I didn't put this No. 1 just because of that.
Of course, the Flyers didn't beat the Rangers in the 2012 Winter Classic. It wasn't lacking in drama either, as Henrik Lundqvist stopped Danny Briere on a penalty shot with 19.6 seconds left, given after Ryan McDonagh was ruled to have covered the puck in the crease. Lundqvist's save preserved the Rangers' 3-2 lead and sealed the victory.
5. Montréal Canadiens (2016)
When the Winter Classic went to Foxborough, Massachusetts, to provide a venue large enough for the storied rivalry between the Boston Bruins and Montréal Canadiens, it meant the visitors from Canada had to go big to stand out, and did they ever.
The Canadiens leaned hard into their history for this look, using the classic "CH" logo they had when they won their first Stanley Cup in 1924 on the front and the globe logo from their 1924-25 jerseys on the sleeves. Putting all these on a bright white jersey with the traditional Habs striping? C'est magnifique.
Canadian teams in the Winter Classic are an unfortunately rare occurrence (something, something ratings, something), but when there's a massive rivalry like Canadiens vs. Bruins, you have to do it right. That Montréal defeated Boston 5-1 at Gillette Stadium should've been a bit more noteworthy in Winter Classic history. However, this game gets a bit lost in the mix, perhaps because of that blowout.
Bruins fans are probably wondering why their jerseys from this game didn't make the cut on this ranking after I listed them so highly a couple of months ago. Listen, you catch me on the right day, and I'll have an entirely different opinion, and this is that day, OK?
4. Boston Bruins (2010)
The first time the Winter Classic was at Fenway Park in Boston, the hometown Bruins hit the ice in black and gold with a strong emphasis on gold.
This jersey is a virtual reverse retro of their home white jerseys from the 1948-49 season. The stylized spoked-B stands out almost as much as the gold base of the jersey, but it all looks really, really good.
And let's be honest, gold can be a tough color to work with if there's not a good style to it. The Bruins leaning on a one-year look from decades ago to make it happen was really smart. Other teams haven't had quite as good luck with gold, but the Bruins have consistently nailed it.
It always helps when a jersey is linked to a happy moment, too.
The Bruins took out the Philadelphia Flyers in the 2010 Winter Classic 2-1 in overtime. Marco Sturm scored the game-winner and sent the Fenway faithful home happy...and probably wearing a snazzy new Zdeno Chara, Patrice Bergeron, Tim Thomas or Marc Savard jersey. Considering the Flyers wore throwbacks to their inaugural 1967 expansion jerseys, it was a very aesthetically pleasing game on top of it all.
3. Toronto Maple Leafs (2014)
I know a lot gets made about the Original Six, and I know there are a lot of people who are very over it, but look...these jerseys are as good as it gets.
There's a ton of history in the Leafs and their looks over the years, and this one is a tribute to their first jerseys as the Maple Leafs from 1927-1930. The crest and the stripes are the same, and the white shoulder yoke helps the whole thing really pop. Add in the lace-up collar, and it has all the feel of being something really old but totally isn't whatsoever.
That season wasn't a super one for the Leafs as they fell apart that winter and tumbled out of the playoff picture, but they could hang their hat on being able to make it out of Michigan Stadium with a win. The Leafs took out hometown Detroit in a shootout in a packed Big House and looked darn good while doing it.
That this style didn't find a way to stick around a little longer is unfortunate because it's really good. I'm not a marketing wizard, but if they happened to do a Reverse Retro spin on this jersey, it might do pretty well.
2. Detroit Red Wings (2014)
Fear not, Red Wings fans—you haven't been forgotten. Given the Maple Leafs' look from 2014 was just ranked, it was impossible to not pick this old-school style look while giving it a slight edge over Toronto.
It has a classic look despite being something completely original. It has the aged white to go with the red, there's the iconic winged wheel, and even the font for the letters and numbers is cool.
Perhaps it's a little bittersweet for Wings fans because it was almost a swan song moment for the likes of Pavel Datsyuk and Henrik Zetterberg. Datsyuk was out of Detroit two seasons later, and Zetterberg retired in 2018, two seasons after the Red Wings consecutive playoff streak ended.
The setting at Michigan Stadium in Ann Arbor, with the Wings in red and the Maple Leafs in blue, made it unique as well. A color versus color matchup in the NHL is something that should absolutely happen more often, and that these two iconic teams rolled it out for the 105,491 fans in the snow and cold made it all the better.
1. Pittsburgh Penguins (2008)
It was the first Winter Classic, and it had the best-looking jersey of them all.
The Penguins faced off against the Buffalo Sabres at Ralph Wilson Stadium in Orchard Park, New York, and came dressed to impress with their throwbacks to the 1969-71 baby blue jerseys. If you're going to use something from the past and give it an ever-so-slight update (the Winter Classic jerseys added names on the back), make it the best one in team history.
Teams had already started using (abusing?) circular logos across the league at the time, so throwing it back to one of the originators of the look may have seemed trite, but look at these beauties. The Pens donning these duds against the Sabres, who busted out their own throwbacks in the setting they had in Western New York with the snow falling, made the Winter Classic the event everyone else across the NHL wanted to get involved in.
It probably didn't hurt that Sidney Crosby scored the winning goal in the shootout to garner attention. However, rolling out with a picture-perfect look in a picturesque setting makes these Penguins jerseys the epitome of what it means to hit all the nostalgic notes and make people want to buy one of their own, too.