From letterman jackets to cowboy hats, coaches know how to look their best for outdoor NHL games. Avry Lewis-McDougall lists five looks that stand out from the past two decades.

For generations, NHL bench bosses have worn the same outfits, but the outdoor nature of games has sometimes forced or encouraged a change of outfit for the games.

While we've yet to learn about what Jay Woodcroft and Ryan Huska will wear at Commonwealth Stadium on Sunday night's NHL Heritage Classic, we can look back on other coaches who've stood out during the Winter Classics and other outdoor games:

Rick Bowness and the Dallas Stars Channel their Inner Cowboys

How can you not play into the area's culture when in Texas? When the Dallas Stars hosted the Nashville Predators in the 2020 Winter Classic, Rick Bowness and his staff, with their letterman jackets, all wore Cowboy hats on the bench at the Cotton Bowl.

While Bowness took his hat off well before the end of the game, it was a fantastic sight to see for the first time coaches play into the cowboy style of Texas with their gameday outfits.

Dan Bylsma was the Perfect Coach to Wear the Fedora

If you sent Dan Bylsma back to the 1940s or 1950s, he'd have fit right in with Toe Blake and Dick Irvin Sr., who wore a fedora behind the bench.

At the 2011 Winter Classic, when the Pittsburgh Penguins squared off against the Washington Capitals, Bylsma brought back the fedora behind the bench successfully. His look with the glasses and letterman jacket easily made him the most dignified man on the Penguins bench that evening at the then-Heinz Field in Pittsburgh.

No One Was Warmer than Peter DeBoer

The Stadium Series in 2014 at Yankee Stadium wasn't the warmest game, so putting warmth over fashion was undoubtedly more important. 

New Jersey Devils coach Peter DeBoer made it work, opting for a beanie and combining it with the Devils team scarf and jacket to give him the look of a super passionate soccer fan.

DeBoer's look was one of a kind, and it may have been forgotten compared to other coaches during outdoor games, but he was able to make it work and show fans how cold it really was.

Bruce Cassidy Pays Tribute to Doc Emrick

There's a lot of love from all over hockey for one of the greatest play-by-play voices, the only Mike 'Doc' Emrick. While the sports and hockey worlds were still trying to tackle COVID-19 in 2021, the NHL got creative in staging another outdoor game.

Lake Tahoe was the venue for two days of NHL games without fans, but coaches still wore special outfits. When the Boston Bruins took on the Philadelphia Flyers that week at the NHL Outdoors at Lake Tahoe event, then-Bruins coach Bruce Cassidy paid tribute to the broadcasting legend who retired from a decades-long career at the end of the 2020 NHL playoffs by wearing a scally cap Emrick gifted him.

It was a great gesture from Cassidy to show his respect for someone who had been the definitive voice of hockey in America for so long.

Craig MacTavish as the Man in Black

The original Heritage Classic between Edmonton and Montreal didn't see either Craig MacTavish or Claude Julien wear anything quirky or team-branded back in 2003. But MacTavish (along with assistant Craig Simpson) rocked a classic black peacoat and black scarf on the bench, giving them a very stoic look leading his team.

The outfit gave him a bit of a James Bond villain look, but it stands out today among the typical letterman jacket look.