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Dirty Harry’s Herringbone Tweed and Red Sweater Vest

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

Vitals

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

Background

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)

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.

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?

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