Few things in baseball are as instantly iconic as a great mustache, and Payton Tolle is proving that true in Boston.
His mustache isn’t just facial hair—it’s a statement. It’s got that perfect mix of swagger and old-school grit, the kind of look that makes you think he was born to wear a Red Sox uniform. Watching Tolle take the bump at Fenway Park last week with that parted pencil ‘stache beckoned like a callback to the days when facial hair was not just part of the team’s identity—like the bushy beards of the 2013 World Series champs—but when having a mustache was an art form, the true handlebar heroes of Red Sox history, the pencil pushing pitchers, the whalloping walruses, the paint brushes painting corners.
Tolle’s glorious mustache truly sparked an idea: what if there was an All-Time Red Sox roster, not just by stats or accolades, but by their facial hair game? From iconic lip rugs to playoff beards, Red Sox fans have seen it all. Tolle’s whiskers could stand among the greats someday, but for now, this All-Time Facial Hair squad sees the best of the best—from the cleanest edges to some truly remarkable cavemen.
BOSTON, MA – AUGUST 31: Mike Napoli #12 of the Boston Red Sox has his beard pulled by teammate Jarrod Saltalamacchia #39 of the Boston Red Sox as he is congratulated at the dugout after scoring during the third inning of the game at Fenway Park on August 31 in Boston, Massachusetts. (Photo by Winslow Townson/Getty Images) Getty Images
The OG of the Beard group of 2013, Mike Napoli’s beard was probably the most iconic on the team. His contributions in 2013—especially in the playoffs—en route to a World Series win made it very easy to put him in this slot.
Studio headshot portrait of American professional baseball player Jerry Remy, second baseman for the Boston Red Sox, late 1970s or early 1980s. (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images) Getty Images
Dustin Pedroia came pretty close to landing in this slot, but RemDawg isn’t RemDawg without his stache. His presence in the NESN booth alongside Don Orsillo is beyond missed and may his memory forever be for blessing.
BOSTON, MASSACHUSETTS – AUGUST 19: Trevor Story #10 of the Boston Red Sox at Fenway Park on August 19, 2025 in Boston, Massachusetts. (Photo by Paul Rutherford/Getty Images) Getty Images
I was a millimeter shy of giving this to Rick Burlseon—his mustache was pretty decent. Still, Story’s beard is almost model-esque. Perfectly full and business professional, just like the way he’s carried himself in inarguably his best season in Boston so far.
Boston Red Sox Wade Boggs before American League Playoff Series against California Angels, October 11, 1986 in Anaheim, California. (Photo by Bob Riha, Jr./Getty Images) Getty Images
I know, I know, he defected to the Dark Side. Still, Mr. Drink All the Beer In the World on a Flight absolutely deserves this spot. Mike Lowell is an honorary mention, but Boggs takes the cake with this classic ‘stache.
ST. LOUIS, MO – OCTOBER 27: David Ross #3 of the Boston Red Sox grabs a beard full of Jonny Gomes #5 after Gomes hit a three-run home run against the St. Louis Cardinals in the sixth inning of GameThree of the World Series on October 27, 2013 at Busch Stadium in St. Louis, Missouri. (Photo by Michael Ivins/Boston Red Sox/Getty Images) Getty Images
Yet another beard pullee of 2013, Gomes was such a glue piece on that roster. And he performed, too, with some absolutely majestic walk-off homers against the Padres and Rays, as well as a dinger in Game 4 of the World Series. Left field was oddly bare for candidates, so Gomes is the standout winner.
Center Field: Johnny Damon
Baseball: ALDS Playoffs: Closeup of Boston Red Sox Johnny Damon (18) before Game 1 vs Anaheim Angels at Edison International Field. Cover Inset. Anaheim, CA 10/5/2004 CREDIT: Robert Beck (Photo by Robert Beck /Sports Illustrated via Getty Images) (Set Number: X72003 TK1 )
Another absolute beast taking the cake here. Damon’s caveman look is picturesque and one of the first things I associate with the Idiots that reversed the curse in 2004. Seeing him downgrade his look when he shaved after joining the pinstripes was absolutely awful.
Right Field: Dwight Evans
BOSTON, MA – CIRCA 1983: Dwight Evans #24 of the Boston Reds Sox looks on prior to the start of an Major League Baseball game circa 1983 at Fenway Park in Boston, Massachusetts. Evans Played played for the Red Sox from 1972-90. (Photo by Focus on Sport/Getty Images) Getty Images
I had Trot Nixon in the slot until the absolute last second. Look at that mustache. Absolute perfection. While Trot did help reverse the curse, Dewey is embedded into the fabric of the Boston Red Sox.
Designated Hitter: David Ortiz
SPRINGFIELD, MA – JANUARY 21: Former designated hitter David Ortiz of the Boston Red Sox speaks during the 2023 Red Sox Winter Weekend on January 21, 2023 at MGM Springfield and MassMutual Center in Springfield, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images) Getty Images
Was this the no brainer of all no brainers? The evolution of his facial hair—the pencil outline beard early on to the clean lines he has now—will forever live on in Boston. You can’t not see Big Papi without his beard. It’s just not possible.
BOSTON, MA – OCTOBER 23: David Ross #3 celebrates with Jonny Gomes #5 of the Boston Red Sox during Game One of the 2013 World Series against the St. Louis Cardinals at Fenway Park on October 23, 2013 in Boston, Massachusetts. (Photo by Elsa/Getty Images) Getty Images
Similarly to right field, I had someone else penciled in here until the very last second—Jason Varitek. But if this is a beard competition—not just an accolades competition—Ross’ is a work of art. The skunk stripe in white, another extremely yankable set of whiskers, it fit perfectly in 2013. Him lifting up Koji is an all-time memory.
Starting Pitching: Luis Tiant
UNDATED: Luis Tiant #23 of the Boston Red Sox poses for a portrait. Tiant played for the Sox from 1971-1978. (Photo by MLB via Getty Images) MLB via Getty Images
Luis Tiant had the handlebars for days. From his pitching days all the way to the very end, El Tiante’s handlebar mustache aged with so much grace. It may even be my favorite of the bunch.
LOS ANGELES, CA – OCTOBER 26: Craig Kimbrel #46 of the Boston Red Sox reacts after retiring the side in the ninth inning against the Los Angeles Dodgers in Game Three of the 2018 World Series at Dodger Stadium on October 26, 2018 in Los Angeles, California. (Photo by Billie Weiss/Boston Red Sox/Getty Images) Getty Images
A wild pitcher in Craig Kimbrel fittingly had a wild, wild beard. As ginger as can be, completely unkempt, it fit his flamethrower activity—and then his wild lack of command in the end—on the bump for his Red Sox career.
What do you think? Who did I miss? Any more honorable mentions?