Dirty Harry’s Clean Style

As many readers of the site have fortified their dwellings into makeshift self-isolation zones, the perfect opportunity to work without disruption also brings the opportunity to surf Amazon Prime and Netflix in equal concentration. In this self-isolation, my thoughts drifted to a style icon often not mentioned. I am speaking about Clint Eastwood as one of cinema’s greatest anti-heroes, Dirty Harry.

Harry Callahan, AKA “Dirty Harry,” not only saves the Bay Area from serial killers and renegade cops, he does so in San Francisco Trad style. Despite the sun beaming, Dirty Harry dresses for the breezy and chilly city in combinations of tweed sport coats with flannel slacks.

In the titular movie, two outfits stand out. The first the outfit worn while foiling a bank robbery: three-button grey herringbone tweed coat, burgundy sweater vest, regimental tie, and grey flannel slacks. The second outfit substitutes the color scheme: Harry wears a checkered brown tweed jacket, light brown sweater vest, with a darker brown polka dot necktie. 

In the second installment of Magnum Force, Harry is seen in his classic Trad style once more. Before foiling a hijacking of a passenger plane, Harry wears his grey herringbone jacket once more with a dark blue patterned necktie.

Of course the looks are extensive and eventually turn more casual as Harry Callahan ages into the ’80s. These early films of the series prove to be gold for the action-hungry Trad enthusiast. Dirty Harry’s style left such an impact that even GQ wrote on getting “the look,” earlier last decade.

If Harry Callahan can jump from bridges, foil robberies, and spar with bad guys while keeping his jacket and tie intact I think we can do our best as we “work” from home. — PL

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14 Comments on "Dirty Harry’s Clean Style"

  1. Plus, the younger Eastwood had cool hair. Not exactly the fetishized Princeton or Harvard cut, but cool nonetheless.

    Best Regards,


  2. One of the coolest/best movie characters — ever.

    Somehow it makes all the sense in the world that he was trad all the way– love the v-neck sweater with Guards stripe repp.

    “that sounds very stylish…” —


  3. Hardbopper | March 25, 2020 at 3:40 pm |

    In one of the movies, I forget which one, Harry’s trousers are ruined by shot-gun pellets.

  4. Charlottesville | March 25, 2020 at 3:57 pm |

    Nice post, PL. I had forgotten how wonderfully stylish and traditional the clothes were in these movies. A far cry from the San Francisco of today, although I think that Cable Car Clothiers is still in business.

  5. Takes a nice bit of tailoring to conceal that .44 Magnum and still look well-fitted. An N-Frame with Roper grips and a leather shoulder holster make for a LOT of bulk.


    I laughed when I saw a recent replay, and he told the ER doctor not to cut his pants because they cost $30 (or some other ridiculously low amount). Decent piece of change in the early ’70s, though.

  6. @Hardbopper

    Pants, the first “Dirty Harry” from 1971. The doctor asks Harry if he tells him how to beat a confession out of a prisoner. (Police brutality was a small price to pay for law and order.)

    I always thought Eric Fleming might have made a better “Dirty Harry” if he hadn’t died earlier. Clint seemed like a sissy in comparison to trail boss Gil Favor in the Rawhide series.

  7. One day, somebody clever and insightful will write the story of Clinton Eastwood’s life. Surely more than one biography awaits the world. At least one of them will (hopefully) turn attention to the focal point his body of work: the study of (and elaboration upon) traditional manhood. As actor, writer, and director, he has been preoccupied with (tormented by?) the question of traditional manhood, including themes of chivalry, honor, in and stoic acceptance, in an ever-changing world.

    It’s no accident that “Dirty Harry,” who stands as metaphor/symbol and emblem (“Go ahead, punk” he dares, while pointing a revolver) against a rising counterculture, wears Ivy. What else, in a world of self indulgent hippies and angry feminists, would such a man wear?

  8. I’ll add that Eastwood’s face and voice compliment the clothing: skeptical squinted eyes, frown, and a dry, raspy,
    whisper. Departing from pure stoicism, he actually gives a damn and expresses discontent. The guy is a genius.

  9. Frank Sinatra was the original choice to play Dirty Harry. He dropped out due to a broken wrist because he couldn’t hold the Magnum properly. I loved Clint Eastwood in the role and he made tweed jackets look cool. The cut and the herringbone cloth are superb. Thank God that the over-rated Sinatra pulled out!

  10. From the traditional, stoic male point of view, his work is important. Many if not most of his characters protest loudly… and, then, with the passing of time and (maybe prayerful) deliberation, stoically accepts the world as is… and adjusts— to survive, to live another day and fight the good fight. But acceptance isn’t synonymous with embrace or affirmation. Quietly and privately, the protest continues…and fuels the perseverance.

    And then there is the abiding suspicion of bureaucracy. This is a theme throughout his body of work. Including and maybe especially his most recent film. What happens when injustice is allowed/advanced by groups of people who are supposed to represent justice? Whether corruption or incompetence is to blame, a response is merited.

    Probably no accident that many of the heroines are feminine incarnations of the traditional strong, stoic man.

  11. Vern Trotter | March 26, 2020 at 12:45 pm |

    In 1962, Clint was a guest star as one of the neighbors in Mister Ed, the Talking Horse. Maybe he was in only one episode.

  12. Roger Sack | March 26, 2020 at 3:37 pm |

    My daughter was married at Mission Ranch, a Clint Eastwood resort
    in Carmel CA. It is an deal spot for a destination wedding where guests
    may take advantage of all the Monterey Peninsula offers. The “Ranch”
    itself reflects Eastwood’s very American aesthetic:


  13. BigRichEnergy | March 26, 2020 at 4:14 pm |

    Isn’t this the guy that talks to empty chairs? And drinks beer with his orangutan? If this is a masculine role model, I’ll pass.

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