Sean Connery Style | 007 Tips to Steal From The Original James Bond

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.

1. Classic Tailoring is Crucial

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.

2. Leverage Texture in Your Suits

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.

3. Don’t Be Afraid of the Three-Piece Suit

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.

4. Pay Attention to the Details

Sean Connery’s Cocktail Cuff Shirts

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

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

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.

Sean Connery’s Rolex

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.

5. Find a Hairstyle That Works (and Stick to it)

“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.

6. Presidential Fold is a Must

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.
  6. 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.

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.

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.

9. Keep it Simple

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.

10. Real Men Wear Kilts

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.

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