Sean Connery embodied James Bond. He laid the groundwork for what would become the longest film franchise ever.

He was an exceptional movie star, actor, sex symbol, and status icon.

Millions of men have looked to Sean Connery’s style for guidance – from his first appearance on screen in 1962 to his more modern cinematic moments.

Connery was the epitome of suaveness, sophistication and manliness.

Today, I’m paying tribute and I’m giving you (00)7 style lessons you can learn to be more like Bond.


Click Here To Watch The Video – 007 Style Secrets To Steal From Sean Connery (The ORIGINAL 007)

Sean Connery Style Tip 1. Classic Tailoring is Crucial

sean connery style classic tailoring

Sean Connery sporting a light grey mohair and wool suit with a dark navy blue grenadine tie from Turnbull & Asser.

From his first appearance as 007 in Dr. No, Sean Connery’s tailoring is on point. In Dr. No, Connery’s wardrobe was tailored and produced by world-renowned Saville Row Tailors. From this point onwards, men across the globe used Connery’s Bond-style as a template for their own fashion choices.

There isn’t a more iconic suit that the glen check three-piece suit from Goldfinger or the classic Midnight Blue Shawl Collar Dinner Jacket worn during his first appearance in Dr. No.

His jackets were tailored with a full chest, a gently nipped waist, and roped sleeve heads. This was paired with trim forward-pleat trousers with side-adjuster. Connery’s suits were made to fit him like a glove.

In fact, the director of Dr. No, Terrance Young, told Connery to sleep in his suits to become as comfortable as he could in them. He did and the effect of shoes. Connery moves in a suit like a cat – smooth every step of the way with effortless sophistication. This couldn’t have been done unless the suits fit perfectly.

Don’t be swayed by tight pants and extremely short jackets you see today – the perfect suit fit will never let you down.

Sean Connery Style Style Tip 2. Leverage Texture in Your Suits

sean connery style suit you only live twice

Sean Connery wearing a grey herringbone suit in You Only Live Twice.

In Dr. No, Sean Connery wears three gray suits – all in different shades. He is known to have a particular fondness for the gray suit however has been known to wear dark blue or brown on occasions. Other than that, Connery wore the occasional dark blue suit or dark brown suit.

The thing that made Connery’s Bond stick is that they are far more than basic solid worsted wool suits. Connery wore shiny lightweight wool, pollen flannels, mohair blends, and duping silk. When he did wear suits made of worsted wool, they had textural patterns like herringbone, pick-and-pick, and various forms of the glen check.

Let’s face it – some men face limitations when it comes to the colors they can wear with confidence. What’s the solution? Textures. They provide a more subtle way to vary the look of your everyday suit.

From Russia with Love give us a great example of this in the suit Connery wears at the end of the film. In Venice, Connery wears a heavy navy flannel suit with grey chalk stripes. The jacket has two buttons with a relaxed fit, draped chest, natural shoulders, and slight waist suppression. The jacket also has flapped pockets, four-button cuffs, and a single vent. The suit trousers match the suit’s pattern with double forward pleats, side button tab adjusters, and turn-ups.

This suit could have just been a standard navy suit, but the added extra detail of a chalk stripe is subtle and allows Connery to stand out from every other man.

Sean Connery Style Tip 3. Don’t Be Afraid of the Three-Piece Suit

 sean connery style three piece suit goldfinger

Connery’s legendary three-piece glen check suit in Goldfinger.

In today’s relaxed culture, three-piece suits can seem overkill. Connery knew the power of it and used it. Starting in Goldfinger and continuing through the rest of his tenure as 007, Connery used the three-piece suit to mix up the status quo.

The three-piece suit is an excellent way to set yourself apart from the crowd, and Connery knew this. Any guy can slip into a two-piece suit but adding that vest is a perfect finish giving you an exquisite and stylish look.

Take Connery’s famous grey and white glen check three-piece suit from Goldfinger as an example. This suit made by Anthony Sinclair (Connery’s tailor of choice) is just a standard two-button suit with narrow lapels and double vents. But by adding a matching waistcoat with six buttons, notch lapels, and four welted pockets, this suit is elevated to legendary status.

Another great advantage of wearing a three-piece suit is that you have more options. By owning a few three-piece suits, you can mix the waistcoat with different jackets and pants from another coordinating suit. This gives you a less formal look but is a style move that most men are afraid to pull off.

goldfinger tweed country jacket

The brown houndstooth check jacket with the odd beige waistcoat from Goldfinger.

Goldfinger is a masterclass of waistcoat style as Connery pulls off an odd waistcoat in the film as well. After returning from a rough hotel stay in Miami, Bond returns to his boss M to report what has happened (and get a scolding from M).

Bond wears a country suit in a mid-brown and black houndstooth check. Under the jacket, we wears an odd waistcoat in beige wool. This makes the suit stand out in a crowd. While not the most appropriate office wear, Connery wears this suit with great swagger and confidence.


Sean Connery Style Tip 4. Pay Attention to the Details

Another way Connery’s style has stood the test of time is the attention to detail he has.

Sean Connery’s Cocktail Cuff Shirts

cocktail cuffs sean connery

The “cocktail cuff” made famous by Sean Connery.

Let’s take his shirts as the first example. Sean Connery mostly wears solid shirts with his suits and sports coats. Connery’s shirts follow English tradition varying in color from plain white, light blue, medium blue, and cream like his suits. How did Connery make these shirts stand out – the cuffs.

Connery wears the cocktail cuff. This cuff is a sorta hybrid between a French cuff and a barrel cuff. This cuff is a double-length-barrel cuff that’s folded over itself with cuff hems on a diagonal line that is fastened with buttons instead of cuff links. This was his go-to cuff for all of this suit (other than dinner jackets)

Sean Connery’s Shoes

sean connery goldfinger

Connery wearing brown suede shoes paired with the brown barleycorn tweed hacking jacket in Goldfinger.

Another example of details Connery’s choice of shoes. From ankle boots to espadrilles, his shoe game was always appropriate and stylish. Connery mostly favored a black three-eyelet derby (blucher) and a two-eyelet derby. In Thunderball, Bond wore a pair of short black boots with his suits. It’s very slight, but eagle-eyed views can catch them at the beginning of the film.

Even though Daniel Craig takes all the credit for making suede shoes cool again, Sean Connery was wearing them all the way back in 1964 and 65 in Goldfinger and Thunderball. These casual two-eyelet derby shoes were in a dark brown suede and looked like a short chukka boot. The soles were dark brown rubber, making them perfect for country wear as Bond wore them in the countryside in both films.

Sean Connery’s Sunglasses

 thunderball sunglasses

The iconic sunglasses from the film Thunderball.

No man can go without accessories, and Connery didn’t disappoint. In From Russia with Love and Thunderball, Connery rocked a pair of black Wayfarer style sunglasses with two rivets on each side and front of the temples. These work both in a dress and casual atmosphere and are effortlessly cool.

These glasses have been remade by the company Curry & Paxton and are still available today. The model is named “Sean” and is a great tribute to the pair worn in Thunderball. Click here to check them out!

Connery’s Bond also wore a few unique hats. In Dr. No and From Russia with Love, Connery wore a trilby. The Dr. No trilby has been identified as being from Lock & Co. Hatters. In Thunderball, Sir Sean wore a pork pie straw hat with a blue and white checked cotton ribbon.

Sean Connery’s Rolex

sean connery rolex

The legendary Rolex 6538 on an undersized nato strap in the film Goldfinger.

For his watch, Sean Connery famously wore a Rolex Submariner 6538 in all of his films. This scarce watch exudes timeless style and elegance. This particular reference of watch goes for anywhere from $92,000 all the way up to $544,939! This watch is ideal for James Bond – it’s durable, precise, and looks great with a tuxedo or a swimsuit.

An interesting feature of the 6538 is the lack of crown guards and the over-sized crown. For the time, this was an oversized crown, and it’s a substantial distinguishing factor from other Rolex Submariners.

Also featured on Connery’s Rolex are the black gloss dial, baton, and dagger markers, as well as a revolving black bezel. Connery wore this watch on a nato strap and a leather strap throughout his tenure as Bond.


Sean Connery Style Style Tip 5. Find a Hairstyle That Works (and Stick to it)

connery hairstyle

Sean Connery in the film Goldfinger.

“If it ain’t broke, don’t fix it.” This statement couldn’t be more true when it comes to your hairstyle. Connery knew this. His timeless side part was a perfect example of this. Short sides, low maintenance, this haircut fit the bill. Even in Connery’s later years, he continued to keep his haircut short and a beard impeccably trimmed.

Don’t experiment with things that don’t need it. Keeping a flattering long-term hairstyle will make you appear confident and self-assured. Connery’s haircut worked with his face correctly, adding a little volume to his hair to balance out the rest of his facial features.

Sean Connery Hair – How to Get the Look:

Wanna know how to get Connery’s side-part? It’s pretty simple, but here you go.

How to Cut:

  • Two inches of length on the top
  • Taper the sides and back to half an inch

How to Style:

  1. When your hair is damp, take a pomade and work it into your hair gently down to the roots
  2. Use a comb to attain your final look
  3. Pro Tip: use a hairdryer as you comb it into place for more volume.

The Side-Part is a timeless look suitable for any situation. Not sure what haircut works best for you? Click here to discover more about picking the right hairstyle for your hair type.


Sean Connery Style Tip 6. Presidential Fold is a Must

pocket square sean connery james bond

Sean Connery sporting a white linen pocket square in Dr. No.

Throughout his first three Bond films, Sean Connery wore a white linen folded handkerchief in his jackets’ breast pockets. This style is most associated with 60’s style and is something that most men neglect these days. In fact, I’ve been complimented many times for the pocket square by random people stating, “They love this look and wish more men would use it.”

Folding a handkerchief to wear as a pocket square is relatively simple. Connery opted for the Presidential Fold, which is the cleanest and most versatile fold to use.

How to Fold Your Pocket Square Like James Bond

  1. Begin with the pocket square face down
  2. Now fold in half from right to left
  3. Fold in half from left to right – leaving a gap at the right side
  4. Next, fold in half from top to bottom
  5. Fold the bottom up and behind the front.

Before placing the now folded pocket square in your breast pocket, you have the option to iron it flat. This will tame the fabric and is likely what Connery did with his springy linen handkerchiefs.

Inserting a pocket square can be a pain – here’s a tip: Fold the handkerchief in half again bottom to top and place it in the pocket with the amount you want to show. To get it to fill the pocket’s height, I hold the top in place while using the back end of a pencil or pen to gently push the pocket square down int the bottom of the pocket.

Connery kept his handkerchiefs looking neat by keeping the edges hidden. Dandies will often show the edge of their pocket square as a sartorial flair.


Sean Connery Style Tip 7. A True Dinner Jacket Is Midnight Navy, Black or White

As Vesper Lynd said in 2006’s Casino Royale – “There are dinner jackets and dinner jackets.” Sir Sean knew this all the way back in 1962. Sean Connery has inspired more men to wear black-tie than any other person. His 007 sets the ultimate example of how to follow the black-tie dress code.

He follows the traditional protocol for black tie dress codes. Connery wore a tuxedo in every one of his films and showed exactly how to pull off the three options you have for black-tie.

Midnight Blue Shawl Collar Dinner Suit from Dr. No and Thunderball

pocket square sean connery james bond

The midnight blue dinner jacket in Thunderball.

In Dr. No, Connery was introduced as the character in a traditional midnight blue shawl-collar dinner suit made by Anthony Sinclair. The dinner jacket featured a shawl collar in midnight blue satin silk, silk gauntlet cuffs that turn back at the end of the cuffs, one button, and two vents.

The turn-backs at the end of each cuff is a unique flair, but a welcomed one. Connery breaks black tie rules slightly by having two vents in the back of his jacket. Traditionally, a dinner jacket show has no vents, but James Bond is a man of action, so it is acceptable. The trousers have a traditional rise and a silk stripe down each side of the leg.

He wears a white shirt with a pleated front, spread collar, and double cuffs that take cuff links. His bow-tie has diamond pointed ends and a white pocket square that matches his shirt in his breast pocket. He finishes the outfit off with black cap-toe oxfords.

Interestingly, Connery doesn’t wear a waistcoat of cummerbund here; however, Bond often doesn’t wear one. I would recommend always wearing a waist covering – only Sir Sean can pull it off without one.  ?

Ivory Dinner Jacket from Goldfinger

goldfinger tuxedo james bond

The ivory dinner jacket worn by Sean Connery in the film Goldfinger.

Just as iconic as the midnight blue dinner jacket that introduces Bond in Dr. No, Sean Connery wears a white dinner jacket at the beginning of the film, which is an excellent option while in a warmer climate.

This dinner jacket isn’t strictly white but somewhat closer to an off-white or ivory. Connery’s Goldfinger tuxedo features peaked lapels that aren’t silk. This is in line with traditional black-tie rules. The jacket closes at the front with a single button and has four-button cuffs. The lower pockets are jetted without flaps, and the back has no vents.

His trousers are black with a double forward pleat, slanted side pocket with a silk stripe down each leg. Connery adds a red carnation in the lapel, which is a huge contrast against the ivory jacket, which adds to the outfit’s flair, making it memorable.

Interesting Note: Daniel Craig paid homage to this tuxedo in Spectre in 2015.

Black Notched Lapel Dinner Jacket in Goldfinger

The notched lapel on a dinner jacket gets a lot of hate. The argument is that these lapels are not formal enough for black-tie. Connery gets a pass here because of the circumstances he is in.

connery black dinner jacket

While having dinner with M and Colonel Smithers in Goldfinger, Connery is wearing a black notched lapel dinner jacket.

The notched lapel is more appropriate here because it is a private dinner and less formal than a large gathering.

The jacket is single-breasted with one button in the front, cuffs with four satin covered buttons.

It’s unknown whether the jacket features vents as the back is never seen. The trousers remain a mystery, but one could surmise they match the dinner jacket and feature silk stripe down each leg and are a double forward pleat (a favorite of Connery’s Bond).

BONUS Style Tip 8. Casual Doesn’t Mean Lazy

james bond goldfinger golf

The iconic golf outfit from Goldfinger.

When Sean Connery did dress casually, he was never sloppy about it. The film that shows the most causal outfits for Connery’s 007 is Thunderball.  Taking place mostly in Nassau, Bahamas, the warmer climate is a perfect opportunity to flex his relaxed muscles.

Connery’s casual outfits were all made from a combination of polo shirts, camp shirts, and swimming trunks.

While on leave at Shrublands health clinic, he wears a black lightweight cashmere long-sleeve polo shirt. The polo shirt has a three-button placket with white buttons. Bond rolls the sleeves up over the elbow. He wears a pair of brown flat front cavalry trill trouser with frogmouth pockets. Because he is sneaking around, he doesn’t wear and socks or shoes.

sean connery style thunderball casual

Connery wears a rose-colored short-sleeve line shirt with a slightly curved hem and small side vents in the Bahamas.

This shirt features a french front with a camp collar and a round breast pocket. Bond wears light blue swimming trunks and a pair of canvas espadrilles.

Connery also wears several other casual outfits and camp-style shirts and polo shirts throughout his tenure. The one characteristic that stays true throughout – he looks the business.

Sir Sean would never be seen wearing athletic shorts out and about or t-shirts. He always elevated his style from others around him, and this includes his causal style.

If you’re interested in any of the casual style shirts Connery wore during his tenure as 007, Orlebar Brown has released several 007 collections with pieces made after clothing from Bond films. Click here to check out Orlebar Brown’s 007 collection.

BONUS Style Tip 9. Keep it Simple

james bond dr no suit

Sean Connery in Dr. No wearing a dark grey flannel suit made by Anthony Sinclair on Conduit St. in London.

Sean Connery avoided wearing overly trendy clothes. In general, he wore classic, timeless pieces. The great part about this is you can take almost any outfit (minus a certain terrycloth playsuit in Goldfinger and all of Diamonds are Forever) from his tenure as 007 and wear it today. Nothing would look out of place or extremely strange.

The strangest look might be the pleats that Connery was so fond of in his trousers, but everything else would match perfectly in today’s world. Therein lies the benefits of avoiding trends.

Instead of spending tons and tons of money on the latest pair of sneakers (that will go out of fashion in a year), use that money on a timeless suit or pair of dress shoes that will never go out style. Investing in high-quality, timeless options will save you money as you can wear them forever.

Stick with timeless, stylish options in an interchangeable wardrobe, and you will not only save money, but you’ll always look amazing.

BONUS Style Tip 10. Real Men Wear Kilts

sean connery kilt

Sean Connery in his custom-made kilt with his custom tartan pattern in the background.

Mr. Connery is Scottish – in case you didn’t know – and he wasn’t afraid to show it. Sir Sean would often wear his Scottish Highland dress as an alternative for black tie.

Sean Connery’s style of kilt was made by Holland & Sherry in Peebles, Scotland, in the finest Scottish cashmere. His kilt is the most expensive ever created in Scotland for $10,000. The tartan pattern of the kilt was specially designed for Sir Sean.

Sir. Sean Connery wasn’t afraid of embracing his roots and showing off his ancestral colors. You shouldn’t be either.

You don’t have to wear a kilt to do this – it can be anything for your ancestors. For instance in America, traditional clothing would be western wear. You could add flannel shirts into your wardrobe or maybe even just maybe cowboy boots in your casual footwear.

If you want to go back further in your family line, research your family tree, and determine exactly where your ancestors came from. Most countries and towns have their own patterns similar to Sir Sean’s tartan design. Have a coat of arms? You could get cufflinks made with your coat of arms in it as a small nod to your history.

BONUS Style Tip 11. Invest in a Quality Robe

goldfinger robe

Sean Connery sporting a black and white nailhead robe in Goldfinger.

In five of his seven James Bond films, Sean Connery was seen in a robe. Sir Sean knew that you had to always look good, and he never scrimped when it came to leisurewear around a home.

In Goldfinger, Connery wears a black and white nailhead silk robe in his hotel suite at the Fontainebleau Miami Beach. This was an ultimate style move. This isn’t something he got from the hotel. The robe has torn back cuffs and a shawl collar with black piping. The robe is tied around the waist with a belt and reaches below the knee. Underneath this silk robe, Connery wore light blue cotton pajama bottoms with a white drawstring.

In Thunderball, Connery briefly wears a navy silk robe with turn-back cuffs and a shawl collar. Earlier in the film, while at the Shrublands health clinic, Sir Sean sports a terrycloth robe with a narrow shawl collar and a belted waist.

The key takeaway – invest in a quality robe. Don’t be like every other guide and wear sweats and a t-shirt around the house. Step up your leisurewear game, and people will notice.

you only live twice james bond bath

The yakata robe in You Only Live Twice.

Suppose you’re feeling very adventurous and have an appreciation for Japanese culture. In that case, you could get a yukata as Connery wore in You Only Live Twice.  Yukata is a casual kimono made of cotton. The name itself means “bathing clothes.” Bond’s yukata is a printed pattern of grey on white the looks like trees and water.


Conclusion – Sean Connery Style Tips

A man who lived on his own terms, Sean Connery set the template for all men to copy – rugged machismo, sly humor, effortless style.

In this article, I broke down eleven Sean Connery style tips to steal and make your own.

  1. Classic Tailoring is Crucial
  2. Leverage Texture in Your Suits
  3. Don’t Be Afraid of the Three-Piece Suit
  4. Pay Attention to the Details
  5. Find a Hairstyle That Works and Stick to It
  6. Presidential Fold is a Must
  7. A True Dinner Jacket is Navy, Black or White
  8. Casual Doesn’t Mean Lazy
  9. Keep it Simple – Avoid Trends
  10. Real Men Wear Kilts
  11. Invest in a Quality Robe

Sean Connery set the style foundation for every other James Bond actor to follow and made an indelible mark on the style world forever. But did you know 007 makes style mistakes? Click here to see the 7 ways James Bond breaks the style rules and still gets the girl.

The post Sean Connery Style | 007 Tips to Steal From The Original James Bond appeared first on Real Men Real Style.

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By: Antonio
Title: Sean Connery Style | 007 Tips to Steal From The Original James Bond
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Published Date: Tue, 03 Nov 2020 12:55:16 +0000