The 2020 Winter Classic Jersey Countdown

In Featured
Jan 1st, 2020

Happy New Year! It’s that time of the year again, when the best hockey game – aesthetically speaking – during the regular season is played. With the 2020 Dallas Stars and Nashville Predators entering the Winter Classic jersey lexicon, the countdown still remains at 26 jerseys worn during the annual game (we moved the two jerseys from the NHL100 Classic to the Heritage Classic Countdown, and of course added the two new jerseys for this year). And now here they are, from #26 to #1.

• More: Heritage Classic Jersey Countdown (2019)
• More: Stadium Series Jersey Countdown (2019)

The first of Washington Capitals’ Winter Classic jerseys, these just don’t have the retro-chic feel that vintage jerseys usually go for, instead looking gaudy and dated. To be fair, I’ve never been crazy about this original logo in the first place (or their current updated version), with a strange, modified Helvetica-esque font. The jerseys weren’t that much better, and it’s apparent when they brought them back for the 2011 Classic. But, the Capitals also don’t have much heritage to draw from, and better these jerseys than bringing back these ones. I understand and appreciate the appeal these jerseys may have, but still, it’s the worst we’ve seen at the Winter Classic.

• More: BTLNHL #24: Washington Capitals
• More: Worst to First Jerseys: Washington Capitals

The Flyers’ look has changed very little over their existence, and since they’d already been to the Winter Classic dance (in 2010 against the Bruins) they had limited options to work with. But, what they essentially did was create a jersey extremely similar to what they already wear, with some slight changes to the piping in a not-so-great way. It’s money in the bank for them, with fans most likely clamouring to buy them up, but it feels like a disingenuous cash grab. A better option? Maybe a play on the old Philadelphia Quakers from the ’30s. But with one of the best logos in the league, and owners of the orange, it’s still a more striking jersey than Washington’s that we’ve already mentioned. And bonus points for the keystone-shaped captaincy markings.

• More: BTLNHL #3: Philadelphia Flyers
• More: 2012 Winter Classic Jerseys Unveiled

It’s not a bad jersey, but it’s a curious choice to use a logo that was only in existence for only one of the Bruins’ 90 seasons (1948-49), using a more fluid and bulbous B rather than the strong and aggressive one they’ve been wearing from years. It’s a bad departure from the Bruins’ otherwise well-crafted brand from the last couple decades. Also, the piping along the shoulder is awkward and doesn’t work that well. And there were a few other vintage options available to them, even possibly the other jersey they wore during that same 1948-49 season, which essentially became their new third jerseys.

• More: HbD Breakdown: Boston Bruins Third Jerseys

For a team with such a storied and rich history (including with their jerseys and uniforms), Chicago hadn’t been able to come up with great concepts for their Winter Classic games before 2019 (foreshadowing). These ones are their second effort and, even though they’re beautiful looking jerseys, they’re almost identical to their current road whites, making these jerseys a little bit, well, normal. At least the rest of the jerseys on this list tried a bit harder. They looked fantastic in these jerseys (which is why they’re not lower in these rankings), but the effort and originality is just not there.

• More: HbD News: Chicago Blackhawks’ 2015 Winter Classic Jerseys Announced

Just go up and re-read that last paragraph, as these are painfully similar. We can now officially say that Chicago gives zero fucks and have stopped trying anything interesting with their outdoor game jerseys. This one gets one notch ahead because at least they used a vintage version of the logo this time.

• More: HbD Breakdown: Blackhawks and Blues 2017 Winter Classic Jerseys

Again, like the Bruins earlier on this list, not a bad choice considering how little their jersey has changed over the years, but it’s a bit bland and doesn’t fully take advantage of the retro look they could have gone for with the opportunity of participating in the Classic. Sure, it’s still an exact replica of their 1926-27 Detroit Cougars jersey, but there’s still room for play here, like designing a better gothic-styled D, and there’s still some other possibilities from their history they could have gone for. I would have loved to have seen a Red Winged variation of this 1928 classic, also when they were the Cougars. They do get extra points for the striped socks though. They’re pretty awesome.

The cummerbund jersey (and yes, I had to look up that spelling)! Of the two Penguins jerseys in the Winter Classics, this one is definitely the weaker cousin. That waist piping is crazy large and while it certainly has a retro thing going for it, it’s a bit much. It could have been a reduced to maybe three baby blue stripes, allowing the logo to get a little bit larger and not compete as much with the cummerbund. On the positive, the Penguins designed something they’ve never actually worn before while still pulling from their original 1967-68 jerseys and logo, both of which only lasted that one season. And the stylized numbers (matching those original jerseys) are great and also represent the very first time an NHL team didn’t wear the standard font of blocked-off corners on a jersey. Too bad it only lasted a season and no team tried anything else until the ’90s. But yeah, just a bit much on the stripes. And regular readers know I’m not a huge fan of the dark navy blue on jerseys: too dark to really read as blue and looks more like black.

• More: Worst to First Jerseys: Pittsburgh Penguins

The Leafs’ second Winter Centennial Classic jersey is a bit confounding. On the one hand, there’s some positive elements to it: the simplicity, the great logo crest, etc. But, it’s also a shit-mix of different elements from their previous jerseys that creates a jersey that seems simple, but complex at the same time and, to top it all off, feels off-brand as it’s a significant departure from their traditional and classic jersey design. Out of context, they’re fine-looking jerseys, but for an event that celebrates 100 years in the league, how can something feel so non-Maple-Leafs-esque?

• More: HbD Breakdown: Red Wings and Maple Leafs Centennial Classic Jerseys

It’s hard to improve on the Blackhawks jerseys in general, and these are certainly great looking vintage jerseys, replicating the team’s 1935-37 jerseys. But I’m also a fan of updating vintage looks to fix design issues that don’t make much sense. In this case, there’s no reason why the logo needs to be that small. It would have been a better jersey if the logo had overlapped the wide white band, and gone into the black. Speaking of which, the black doesn’t bother me as much here as there’s lots of colour to break it up. These jerseys are definitely still vintage-looking and fitting for the game and venue, and it’s much more of an effort than their 2015 and 2017 Winter Classic jerseys, but could’ve used some slight changes.

These firemen jackets hockey jerseys are a decent homage to the Bruins’ 1924–25 jerseys, almost replicating them exactly except for one major detail: they’re black instead of brown. This makes the jersey appear more modern instead of retro, but with retro detailing, so the combination becomes off-kilter. But the details are fantastic, from the simplicity of the stripes and the actual fuzzy texture of the bear on the logo, they got a lot of things right. But the colour choice is a complete missed opportunity, with no legitimate reason as to why it was changed.

• More: HbD Breakdown: Bruins’ Winter Classic Jerseys

The first entry from this year’s Winter Classic features the Predators’ Dixie Flyers-inspired jerseys. Is this a bad design? Definitely not, but it’s a little bit underwhelming given what the Preds and Adidas were working with. It’s a golden (pun intended) opportunity for a color vs. color match up with the Stars’ green jersey that never was, and while the details like the shoulder patch and guitar frets inside the collar are really nice, it’s an overall fine, but not stellar, sweater.

• More: HbD Breakdown: 2020 Winter Classic Jerseys

This is very close to the jersey they currently wear, but don’t forget when this game happened. This is the game that reminded people how nice of a jersey it was, especially when compared to their more recent redesigns, including the buffalo zombie and the golden slug, which is what their actual jersey was at this time. It may not be considered classic or vintage now, but it certainly was in 2008. Any time a one-off jersey can influence a change of their current logo/jersey, you know you have a pretty good thing happening. And just when Sabres’ fans thought bad design was a thing of their team’s past, this came along. But that’s a whole other discussion.

• More: Worst to First Jerseys: Buffalo Sabres

The Red Wings’ second entry into the Winter Classic jersey archive is miles ahead of their first one, and there’s a lot to love about this jersey. It’s a mixture of their 1927-28 and 1928-29 Detroit Cougars jerseys, with a stylized version of the ’30s-era Red Wing logo brought in. It looks vintage, with some contemporary elements brought in and relatively consistent striping. A solid Winter Classic entry. My main gripe is the “Detroit” and numbers typeface, which looks like a contemporary font trying to be vintage. Also, more space between “Detroit” and the logo please. Of note, it looks like the captaincy marking has been moved to a diamond shape on the left sleeve, which is a very non-traditional move. It’s also against league rules, so I imagine the league gave them special permission, as they did for the Sabres. I like it better on the sleeve than on the shoulders, as the Sabres did, and it works for a one-off jersey. A regular jersey, I’m not so sure.

• More: HbD News: 2014 Winter Classic Jerseys Announced

It’s a double dose of Detroit (like a Double Dion?), with the Centennial Classic jerseys jumping on the list just ahead of their 2014 Classic jerseys, and this feels more like a classic Red Wings jersey: simple, iconic, historical striping, and a callback to what they wore when they were known as the Cougars. What make this one stand out a bit more too is the classy inclusion of the silver, with a single sleeve stripe that includes all the years they’ve won the Cup. If I’m a Detroit fan, I want one. It’s a great commemorative jersey for one of the longest running teams in the league.

• More: HbD Breakdown: Red Wings and Maple Leafs Centennial Classic Jerseys

The Rangers’ jerseys are a great look for a team that also hasn’t changed their look much over their existence. The piping is great, the off-white base is perfect, and while it certainly draws from their current jersey and look, it’s enough of a variation to give it a vintage look. Stripes on the shoulder yokes seems to be an emerging theme for vintage-based jerseys, a commemorative look of when stripes overtook a jersey completely. A single stripe, as is the case here, works. But please don’t let it go too far. Essentially, the jersey isn’t an exact replica of any of their past jerseys, but it looks like it could be. The logo itself is an updated replica of their original logo from the ’20s and ’30s.

• More: 2012 Winter Classic Jerseys Unveiled

Another jersey that spawned a redesign of the permanent jersey design for the Flyers. Like the Sabres’ Winter Classic jersey, it doesn’t look classic now, but it was a bold choice in 2009, simplifying the overall design and piping of the jersey and letting the loud orange colour do its job of demanding attention, replicating their original 1967 jerseys. The box surrounding the nameplate on the back of the jerseys works really well when the jersey is simplified in this way. In short, it worked so well and was liked so much, it became their new permanent look. When you have such a stable visual brand as the Flyers have had since their inception back in 1967, this is definitely a good thing.

• More: Worst to First Jerseys: Philadelphia Flyers

If there’s one team that’s had an incredibly consistent jersey design, it’s the Leafs, which is remarkable since the franchise been in existence for almost 100 years now. Since 1927, they’ve worn either white with a blue logo and stripes or blue with a white logo and stripes. So, how do you make a jersey that you’ve always worn look vintage? You replicate your (almost) original 1927 Maple Leaf jersey, wonky logo and all. It fits the brand, it looks vintage and, because of the simplicity of the blue/white, the crazy striping is necessary to bring out that vintage feel. I would never want this as a permanent jersey, but as a one-off game like the Winter Classic, it’s perfect for the Leafs.

• More: HbD News: 2014 Winter Classic Jerseys Announced
• More: Worst to First Jerseys: Toronto Maple Leafs (Redux)

For an outdoor matchup of two of the league’s oldest franchises, the Bruins threw it all the way back to the 1930s for their Winter Classic jersey inspiration. It’s a really great hybrid between the classic style of the league’s early years and the more contemporary jerseys of today. While there are some slight changes we’d like to have seen, overall these are really stellar. This a great build on the 2016 concept that fell a bit short in terms of visual interest.

• More: HbD Breakdown: 2019 Winter Classic Jerseys

The second entry from this year’s 2020 Winter Classic features jerseys that draw from the history of hockey in Texas. Overall, these are really stellar. With questions around what era the team should draw their inspiration from, the direction Adidas and the Stars’ management ended up taking is pretty fantastic. Are there some flaws? Sure, but for the first time seeing a) southern and b) newer franchises in the Winter Classic, these are a great homage to hockey history in a southern state.

• More: HbD Breakdown: 2020 Winter Classic Jerseys

There have been some beautiful match-ups in the last decade of these games, but 2018 might mark the best effort from both teams with their jersey designs. Where the NHL100 Classic tried to bridge the gap between historical and modern aesthetics…and failed, these jerseys succeeded. This Rangers jersey…it’s unique, it’s bold, it looks great, and it just needs to lose that chest patch. That one little detail may have just cost them a spot or two in these rankings, but the jersey’s easily superior to their previous Winter Classic edition, and that was a pretty nice one too.

• More: HbD Breakdown: 2018 Winter Classic Jerseys
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The two 2018 Winter Classic jerseys come in right after each other. Equally fantastic is the Sabres edition, which blends both modern and traditional aesthetics really well while infusing the jersey with lots of character and intensity, and it could possibly be the best jersey that the Sabres have ever worn.  They come out slightly ahead of the Rangers because of a small mis-step from New York (read above) and because of that awesome buffalo shoulder patch.

• More: HbD Breakdown: 2018 Winter Classic Jerseys
• More: Worst to First Jerseys: Buffalo Sabres

It was the first new Habs jersey concept since 1944, and it was worth the wait. These things are just fantastic. Old without looking dated. New while still looking vintage. It strikes an almost perfect balance between jersey design innovation and paying homage to the Habs’ storied past. And the inclusion of the globe on the sleeves – drawing from their 1924-25 jerseys – is a unique addition that delves into their history. When Bruins fans are even admitting they’re nice jerseys, you know you’ve got something good. Nobody seems able to do jerseys quite like the Canadiens do.

• More: HbD Breakdown: Canadiens’ 2016 Winter Classic Jerseys

Finally! The Blackhawks do something interesting! Black jerseys are usually bad, but this one is definitely not. It’s rooted in the history of a team that has some very deep roots, bringing something unique from their first Cup winning team in 1934 back to life. It uses its monochromatic appearance as a strength rather than a weakness to create something visually interesting and attention-grabbing. Any Blackhawks fan should be slobbering to add this to their jersey collection, and it’s a welcome addition to the Winter Classic jersey library. The “21” Stan Mikita memorial patches are the icing on the cake.

• More: HbD Breakdown: 2019 Winter Classic Jerseys

The Blues enter the Winter Classic jersey library with an instant classic (and get bumped up from last year’s list). Everything about it is old-school, but in a surprisingly refreshing way, with a sky blue jersey we haven’t seen since the days of the Nordiques, along with a fantastic classic logo that just never gets old (well, depending on what you add to it). The ribbed sweater collar is great, as is the the classic striping. Basically, for a first attempt at a jersey that celebrates the franchise’s, league’s and hockey’s history, St Louis couldn’t have done much better. For a team that wandered in jersey design Siberia for many years, they’re doing fantastic work recently…aside from bringing those awful jerseys back.

• More: HbD Breakdown: Blackhawks and Blues 2017 Winter Classic Jerseys
• More: Worst to First Jerseys: St Louis Blues

Having already used up their original jersey design for the 2011 Winter Classic (and again, thankfully avoiding bringing up the awful blue eagle look from the ’90s–’00s), the Capitals delved deep into Washington hockey history, creating a jersey that looked unique, historical and innovative all in one. That, and it just looks damn good. You may not like the striped shoulder yokes, but there’s no question it’s historical, and it’s used in a way that balances simplicity and complexity in a single design. Ask any designer, pulling all of this off all in a single design is an incredibly difficult feat. And it works excellently here. It’s still incredibly unique and impactful in the modern era of hockey jersey design. I just wish we’d see more of it.

• More: HbD News: Washington Capitals’ 2015 Winter Classic Jerseys Announced
• More: Worst to First Jerseys: Washington Capitals

When these jerseys first stepped onto to the ice in Buffalo in 2008, they looked damn good. They were a complete departure from anything the Penguins had word in the previous 25 years, but were almost a complete replica from their 1970-71 jersey. The baby blue was a bold and daring colour choice, and pretty much unused in the the NHL since the Penguins themselves abandoned it in the late ’70s. The piping, simple and strong. Outside, against the white sheet of ice and the dark blue sky, they looked great and, even after a full decade has passed, still set the bar for what Winter Classic jerseys can be and represent. This jersey almost single-handedly introduced a new wave of retro jersey and logo designs that persist to this day. An instant classic. Absolutely beautiful.

• More: Worst to First Jerseys: Pittsburgh Penguins

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