Dirty Harry’s Herringbone Tweed and Red Sweater Vest

Clint Eastwood in one of his most iconic roles, Dirty Harry (1971).

Clint Eastwood in one of his most iconic roles, Dirty Harry (1971)


Clint Eastwood as Insp. Harry Callahan, renegade San Francisco inspector

San Francisco, Summer 1971

Film: Dirty Harry
Release Date: December 23, 1971
Director: Don Siegel
Wardrobe Credit: Glenn Wright


Voted the “Greatest Movie Badass of All-Time” in a 2009 poll for MTV News, the character of Harry Callahan was originally much different. Although still a tough cop chasing a serial killer with a .44 Magnum, the role was originally envisioned as an older New York City policeman that was gunned down by a sniper during the finale. Offered first to Frank Sinatra, whose wrist injury from The Manchurian Candidate prevented him from firing the .44, then to John Wayne, who refused to accept one of Sinatra’s rejected roles and later proved his regret by starring in McQ, Clint Eastwood was finally offered the role.

One of my first posts was about a similar San Francisco inspector who plays by his own rules. However, Bullitt and Dirty Harry are two very different policemen: both have their own methods and are disliked by superiors, but where Bullitt is more free-wheeling and liberal, Callahan is shoot-first, ask-later and considerably anti-crime.

This change is reflected in their wardrobes as well. Bullitt prefers a casual look, layering a raincoat over a tweed jacket and jumper. Callahan, the more conservative cop, also wears a tweed jacket but with a necktie and sweater vest. Interestingly, and perhaps not too coincidental, Rick Santorum sported sweater vests when he was an early contender for the Republican presidential nomination in 2012. Perhaps Santorum felt that channeling a conservative film hero would make him more appealing? (And that’s as political as this blog will ever get.)

What’d He Wear?

As mentioned in the Bullitt post, San Francisco is not a place for T-shirts and shorts. Callahan smartly layers up with a tweed sport jacket and sweater vest over his tie and slacks.

The sportcoat is a gray single-breasted herringbone tweed coat with dark elbow patches. There are 3 buttons in the front and 2 on each cuff. Harry often closes the middle button of the coat over his sweater. It has a long single vent in the back. Despite being from the 1970s, Harry’s sportcoat is not very dated, with only mild swelled edges and standard lapel sizes.

Harry’s best side must be his left side?

Harry’s maroon sweater shines a bright red in some light. He coordinates it with a Brigade of Guards regimental striped repp tie, with thick left-shoulder-down-to-right-hip British-style maroon and navy stripes. His shirt is a pale blue with button cuffs and a long point collar.

Clint Eastwood won the Academy Award for Best Steely Gaze in 1971.

Evidently, Harry is very choosy about his pants, a pair of slim cut charcoal flannel trousers with side pockets, belt loops, and cuffed bottoms. After getting some buckshot in his leg, Harry is given the option to have his pants cut off or painfully remove them himself. When the doctor warns him that the latter option will hurt, Harry shows that a BAMF can be frugal as well: “$29.50, let it hurt.” That would be just under $170 in 2012 dollars.

Strangely, although buckshot damaged his leg and got his blood on his $29.50 pants, there were no rips or damage at all to the actual pants. Movie magic?

Harry wears a black leather belt with a gold single-prong buckle. It is this belt that assists with Harry’s most famous piece of attire: the massive light brown leather shoulder holster for his Smith & Wesson .44 Magnum revolver. The holster was made by Bucheimer-Clark and copies made by Lawman Leather Goods are still for sale on their page.

If you’re not wearing your shoulder holster when you go to your doctor’s, you’re DOING IT WRONG.

On his feet, Harry wears a pair of black leather dress shoes with laces and black socks.

Harry’s few accessories are minimalist, practical, and good quality. His Timex watch is stainless with a thin stainless expanding bracelet and a white face.

The recoil from Harry’s .44 gives us a look at his watch, cuffs, and elbow patches. Aren’t we lucky, punks?

Finally, Harry wears black-framed Ray-Ban Balorama wraparound sunglasses. Launched in the late ’60s, these frames were also worn by Eastwood in the Don Siegel-directed Coogan’s Bluff (1968).

Harry in his Ray-Bans.

The wraparound Balorama frame was launched by Ray-Ban in 1967 and remains most popular in the black-framed, green-lensed configuration: Prices and availability current as of Nov. 22, 2023.

Go Big or Go Home

One word that can be used to describe Harry is American. He has a clean and classic American look, even wearing red and blue like the American flag. His gun—and a big one at that—is a Smith & Wesson, an American manufacturer dating to the 1850s. His car is a midnight sapphire 1968 Ford Custom, a no-frills sedan with a powerful V8 engine that would beat any standard four-cylinder rice-burner on the roads today.

And, of course, this opening sequence introduces us to Harry’s “usual lunch”—a hot dog on a bun. Despite its German origins, frankfurters are now regarded as an American staple, seen at picnics, ballgames, and cookouts.

To be “Dirty Harry” Callahan, you just need to be American.

The best opportunity Dirty Harry has for relaxation is when buckshot is being removed from his leg. Naturally.

The Gun

Dirty Harry’s Smith & Wesson Model 29, a .44 Magnum revolver with an 8 ⅜” barrel, is his iconic weapon quoted as “the most powerful handgun in the world”. The .44 Magnum cartridge was initially developed by Elmer Keith for Smith & Wesson. The Model 29 was introduced the same year as an item in Smith & Wesson’s large N-framed series. The official “Model 29″ nomenclature was designated two years later. The Model 29 is a double action revolver with a six-round cylinder and has been offered with 3″, 4″, 5″, 6″, 6½”, 8⅜” and, later, 10⅝” barrel lengths. It had value amongst handgun enthusiasts and some hunters throughout the first sixteen years of its existence, but with Dirty Harry‘s release in 1971, it became wildly popular and shops had trouble keeping it in stock.

A Smith & Wesson Model 29 with the 8 ⅜”barrel, as carried by Clint Eastwood in Dirty Harry.

In this first film, Harry carries his 6 ½”-barreled S&W Model 29 in a light brown leather Bucheimer-Clark right-handed draw shoulder holster with a sewn yoke, tension screw, and narrow belt strap. The rights were purchased by Jerry Ardolino in the 1970s after the company folded. Lawman Leather Goods produces a high quality similar holster although it has a laced yoke, no tension screw, and a wide “cobra head” belt strap. The rumors of an 8 ⅜” barrel or different caliber models being used in “Dirty Harry” are untrue, although 8 ⅜” barrels were used in some publicity photos. (Thanks to Jim Tusing and Max Simmons, two great followers of this blog, for the information.)

From the imfdb article on Dirty Harry:

As the script originally called for a Smith & Wesson Model 29 with a 4″ barrel, this eventually proved troublesome for the filmmakers, since the Model 29 was no longer in production at the time. Before shooting began, Eastwood contacted Bob Sauer (then a representative for Smith & Wesson) to acquire the gun for the film. It was a challenge, but Fred Miller at the plant had a couple assembled from parts eventually. To better familiarize himself with the weapon’s handling and recoil, Eastwood took one to a gun range and fired live rounds through it. Unlike the gun in the script, the only barrels acquired for the guns in this film were the 8 ⅜” barrel and the 6 ½” barrel. Both can be seen used in some scenes. The blanks it fired were custom made since the 5-in-1 blank didn’t fit the chambers. It is said scriptwriter John Milius as presented with one of the actual guns used in the film as a gift later on. As for Harry’s line in the film about the .44 Magnum being “the most powerful handgun in the world”, one should note that even in the 1970s, the .44 Remington Magnum cartridge had been eclipsed in size and power by the .454 Casull round, however, the first widely available commercially sold revolver chambered for the 454 Casull would not come for another ten years, so his statement for the time frame is accurate.

Harry’s use of the .44 Magnum Model 29 was both iconic and influential; the next James Bond film after Dirty Harry, Roger Moore’s first outing in Live and Let Die in 1973, featured Bond wielding the massive Model 29 during the finale, worn in a similar shoulder holster as Harry’s.

How to Get the Look

Clint Eastwood in one of his most iconic roles, Dirty Harry (1971).

Clint Eastwood in one of his most iconic roles, Dirty Harry (1971)

Harry manages to pull off this look—very prep and conservative in other settings—like a BAMF would and not just because he’s Clint Eastwood. He walks with confidence and assurance, wearing what he does because it is practical and comfortable and not to make a fashion statement.

  • Gray herringbone tweed single-breasted 3-button sportcoat with notch lapels, slight swelled edges, welted breast pocket, flapped hip pockets, long single vent, dark right and left elbow patches
  • Pale blue poplin shirt with long point collar and 1-button barrel cuffs
  • Maroon & navy striped Brigade of Guards regimental striped repp tie
  • Burgundy red sweater vest
  • Charcoal pleated slacks with side pockets, belt loops, and turn-ups/cuffs
  • Black leather belt with a gold single-prong buckle
  • Black leather derby shoes
  • Black dress socks
  • Ray-Ban Balorama wraparound sunglasses
  • Timex analog wristwatch with an expanding stainless bracelet and a white dial
  • Bucheimer-Clark light brown shoulder holster (RHD) with a sewn yoke, tension screw, and narrow belt strap, to carry a Smith & Wesson Model 29 revolver

Do Yourself a Favor and…

Check out the Dirty Harry collection.

The Quote

You’ve heard it a million times, probably bastardized, but here it is:

I know what you’re thinking. “Did he fire six shots or only five?” Well, to tell you the truth, in all this excitement I kind of lost track myself. But being as this is a .44 Magnum, the most powerful handgun in the world, and would blow your head clean off, you’ve got to ask yourself one question: Do I feel lucky? Well, do ya, punk?

Harry never actually says “Do you feel lucky, punk?” in this scene.
Do you feel stupid for always quoting it that way, punk?


    • Max

      Nice article in the most recent American Rifleman about the Model 29 that Eastwood & Warner Bros. presented to John Milius at the end of production for Magnum Force. Also delves into the back-story of the guns that actually made their way into Dirty Harry. Roy Jinks evidently tells a story different from the one on IMFDB.

      • Jim

        THE IMFDB has numerous errors. The picture of the 6 1/2 inch M29 is a picture of 6 inch M29. How can you tell the 1/2 inch difference? The barrel is not pinned. 6 1/2 inch barrels were pinned.

  1. Max

    Outstanding. Very nice catch on the wristwatch especially. Perhaps the best part of the character’s wardrobe is that he follows up the initial violin teacher outfit with a chemistry teacher plaid jacket (also with sweater vest) in the next segment and dares you to snicker. True BAMF.

    Word is that you order the holster from Lawman at your peril, i.e., he takes cash up front then ignores your calls and e-mails for 2-3 years, although most people appear to get their holsters eventually.

    Keep up the excellent work! Always eager to see what comes next.

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  4. jim

    Lawman Leather wasn’t around until the mid to late 1970’s so they didn’t make the holster. The holster was probably made by Bucheimer-Clark. Also the S&W Harry used had a 6 1/2 inch barrel not a 8 3/8 barrel.

    • luckystrike721

      Thanks, Jim. This is the first I’d heard of that, but after doing a little digging around, it looks like you’re right on the money with this one. I’ll make some changes and give you credit in the article. Also, at http://www.imfdb.org/wiki/Dirty_Harry, it is written that both the 6 1/2 and 8 3/8 barrel models were used on the film.
      As a side note, have you ever fired a Model 29? Still on my to-do list.

      • jim

        A 6 1/2 inch gun was in the movies while some publicity shots used the 8 3/8 inch gun. Often sited as a 8 3/8 gun in the movie is when Harry shoots the Scorpio killer on the football field. The gun barrel looks extremely long because of the camera angle but it is a 6 1/2 barrel. One of the guns used in the movie is in the NRA museum while the other was returned to the prop company. Also of note is that as the movies progressed Harry’s gun was a contemporary version of the S&W Model 29 available at the time. S&W replaced the 6 1/2 inch barreled guns with 6 inch versions in the late 70’s early 80’s. As a result, the last three Dirty Harry films had Harry toting a 6 inch Model 29. Also, the holster Harry used in the latter films was not the Bucheimer Clark holster seen in the first films but a Bianchi X2000. This is seen in Sudden Impact where Harry is in the woods shooting his 44 AutoMag. WHile watching this scene take note of the continuity error where the straps on Harry’s holster change position.

        And finally, (whew) – yes I’ve shot the S&W 44 Magnum many times. I’ve owned one for almost 30 years. With 44 Specials it’s a very pleasant gun to shoot. With 44 Magnums I don’t find the recoil all that bad but it is very noticeable. I carried the gun for several years in Bucheimer Clark or Bianchi shoulder holsters. The gun is extremely accurate and in this day of just about everyone carrying autoloaders it gets attention at the range. When asked why I carried a S&W Model 29 I usually replied “Shooting more than once to put a target down is just plain silly.” When you get a chance to fire a Model 29 jump on it. You’ll smile big after shooting it.


        PS – Great blog btw. I sent the link to several friends.

      • Max

        My understanding is that Bucheimer manufactured the holster using a pattern devised by Jerry Ardolino who shortly thereafter took his design and had it manufactured through his own shop starting around 1975. I think the company has had a few names over the years, but Ardolino has been the constant. He suffers probably the worst reputation for customer service I’ve ever heard of, but they are damn fine holsters. I picked one up on eBay last November, and it is the perfect fit for my 29-2 (vintage 1974, 6-1/2 in. barrel).

        The character Dirty Harry carries a 6.5″ version (although I suspect it may have been 6″ in Sudden Impact and/or Dead Pool, since S&W switched to 6″ for some time during that period). In some shots for effect, however, they used an 8-3/8″, most notably when Harry shoots Scorpio at the football stadium. Rumors have been around forever that the guns were actually Model 25s in .45 Colt used for the ready availability of blanks and the more dramatic bore (.454 vs .429), but I’ve never seen it substantiated, and Milius insists they were all .44s.

        • jim

          Jerry Ardolino did not design the holster. The holster was designed by Clark in the 1950’s. It can be seen in the movie “It’s a Mad Mad Mad Mad World.” Spencer Tracy’s character, Capt. T. G. Culpepper, wears one. Since the movie came out in 1963 Jerry would have been a young teenager when he designed it. Jerry bought the rights to the holster in the 70’s when Bucheimer-Clark folded. Also, the holster offered by Lawman Leather is not an exact copy of the Bucheimer-Clark used in the movie. The holster used in the movie has a sewn yoke, tension screw and narrow belt strap versus Lawman Leather’s laced yoke, no tension screw and wide “cobra head” belt strap. The holsters produced by Lawman Leather are indeed high quality and will last a lifetime.

          The story that Model 25’s were used in the movie has indeed been around and is wrong. Model 25’s at the time were not chambered in 45 Colt. The last run of S&W 45 Colts was in the late 1950’s early 60’s and only a few hundred were made. The Model 25-5 in 45 Colt wouldn’t be a cataloged item until 1979. 44 Special blanks were used in the gun in the movie. Also, in the high def DVD’s of the movie the guns are marked 44 Magnum on the side of the barrel.

      • luckystrike721

        Jim & Max,

        You guys are treasure troves of information – Thanks! Plus, you both have S&W .44 Magnums, which elevates you into a higher category of Man than most could strive for! The only Smith revolver I have right now is a .32 Hand Ejector manufactured in the ’30s… certainly not very powerful, but fun to take to the range and interesting for its historical value.

        To be safe, I want to confirm the following info before I incorporate it: In the first film, Harry carries his 6.5″-barreled S&W Model 29 in a Bucheimer-Clark holster with a sewn yoke, tension screw, and narrow belt strap. The rights were purchased by Jerry Ardolino in the 1970s after the company folded. Lawman Leather produces a high quality similar holster although it has a laced yoke, no tension screw, and a wide “cobra head” belt strap. The rumors of an 8 3/8″ barrel or different caliber models being used in “Dirty Harry” are untrue, although 8 3/8″ barrels were used in some publicity photos.

        Max – Mind if I ask how much the Ardolino holster set you back? If you’d like, you can just answer in degrees of reasonability (“very reasonable” to “broke the bank”).

        Jim – Glad to see the mention of “It’s a Mad, Mad, Mad, Mad World”, one of my favorites when looking for a classic comedy to watch. Also, people seem to respect the “Why shoot more than once” argument – myself included! Lee Marvin had said that he had live-fired the S&W .44 Magnum prior to filming “Point Break” and found it to be much smoother than he anticipated and he had to fake the recoil for the film itself when the director said he made firing it look too easy.

        Thanks for the help and keep reading,

          • Max

            It doesn’t surprise me in the least to learn that 90% of what Ardolino says is B.S. If he didn’t produce (eventually) quality holsters, he’d probably have been completely discredited by now. I got my holster in near-pristine condition for $140 and have seen them go for as much as $400. I literally fell asleep while trying to win a Bucheimer that went for $225 and have been kicking myself ever since. In addition to the 29-2 (which gets fired about six days out of the year) I have a 29-8 Mountain Gun that I regularly abuse (and that sometimes abuses me, depending on how what I load it with).

            The strangest rumor I ever heard on this topic was that the guns were actually Model 57 .41 Mags because S&W had stopped producing the Model 29 — as if under such conditions S&W would opt to keep the 57 in the catalog rather than the 29.

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  12. Ryan Hall

    Harry wears the jacket later in the film again with black slacks. Shows how he only needs a few sport coats, a few different coloured slacks and he has then many outfits simply by mixing and matching.

  13. jack baumun

    You say little about Dirty Harrys’ dress shirt – a brief mention on it being pale blue ; on VHS it looks white .

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  17. theelectricshadow

    ❤️GREAT POST. Love it. Especially regarding the sansabelt trousers or whatever they were. $29.50, bullets will not penetrate this fabric, just your skin – you’ll get bloodied, you may bleed to death but your pants – intact forever!

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