‘The Instigators’ Pays Homage to Boston Workwear, the Red Sox and ‘90s Heist Films 

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When the trailer for Apple TV+’s new heist film, “The Instigators,” came out this summer, costume designer Charlese Antoinette was surprised to see that the costumes made an impact on viewers. 

The film, which stars Matt Damon and Casey Affleck as partners in crime who set out to rob a corrupt politician in Boston only for their plan to go completely wrong, made an early impression for the vintage Red Sox jackets worn by Jack Harlow in the trailer. The film hits the streaming service on Friday.

“It’s funny, it’s one of those films that I’m like, ‘Oh, it’s not really a film for costumes like that,’ but then people started bootlegging Jack Harlow’s look when the trailer came out,” Antoinette said. “They started bootlegging his vintage Red Sox jacket.” 

Despite her surprise, “The Instigators” has many layers to its costumes. The film’s looks, particularly Damon and Affleck’s, give a nod to Boston workwear and ‘90s heist films with vintage and thrifted pieces. 

Antoinette’s approach to the film’s costumes was anchored in creating an accurate portrayal of Boston, as the movie involves many different types of police officers and firemen from the city. She did extensive research on the uniforms of Boston police officers and even got support from the Boston Fire Department to utilize actual uniforms for the actors. 

Matt Damon and Casey Affleck in “The Instigators”

Courtesy of Apple TV+

“We had times where we were on the street with the real Boston cops and our Boston cops and we were confused,” she said about the costumes. “We really just want to make it feel accurate, especially if you’re from Boston. It’s such a celebration of the city, too, just the way it’s shot. We really wanted the people of Boston to feel like we did our thing to make the characters feel like they were from there.” 

This authenticity also came through Damon and Affleck’s costumes, which were mostly thrifted or aged workwear pieces.

For Damon’s character, Antoinette explained she wanted to show his depression through his outfits. She dressed the actor in thrifted utilitarian and workwear pieces like flannels, faded sweaters and denim pieces.

Affleck’s character had a similar vibe, however, Antoinette wanted the character’s costumes to reflect his relaxed attitude. The character similarly wears workwear styles and also favors hoodies, which Antoinette said reflects how he is hiding a lot in the film.

“We wanted a lot of comedy to come through and also just him not giving an ‘F’ about anything,” she said. “We wanted it to feel like when you see him, it’s like you know who that guy is. He kind of doesn’t give a crap. He’s there to crack jokes. He’s not really taking himself or anything else or anyone else around him seriously, so his clothes aren’t serious.” 

This strategy continued to Affleck’s footwear. Antoinette thought name-brand sneakers would be too flashy for the character, so she ultimately went with a pair of non-descript Phat Farm sneakers from Kmart.

Jack Harlow in

Jack Harlow in “The Instigators”

Courtesy of Apple TV+

Antoinette also thrifted many of Harlow’s outfits. The character works at Fenway Park as a groundskeeper, so she wanted to pay tribute to the Red Sox through his costumes by dressing him in various vintage Red Sox jackets. 

“When you shop for contemporary Sox jackets, everything’s just so shiny, sleek and chic,” she said. “It was really cool to put those jackets on him and that made him feel like a really diehard fan, or that he had inherited those jackets, like they were passed down through his father or grandfather.” 

As Harlow is a New Balance brand ambassador, Antoinette also worked with the brand to dress him in several pairs of sneakers for the film.

Antoinette also wanted to give a nod to ‘90s heist movies with Harlow’s costumes. She dressed him in several Sergio Tacchini tracksuits, stating the style had its heyday in ‘80s and ‘90s heist films. 

The costume designer explained the film was a fun project for her considering much of the costumes were thrifted finds. 

“I love thrifting,” she said. “I love the treasure hunt of it all.”  

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