James Bond’s Tailored Casual Trouser Style

People usually think that a tailor is who they see for clothes to wear when dressing up, but they can be much more than that. Tailored trousers, for example, can be used to make a person’s casual style more elegant. They are stylish for daily casual wear as well as for business casual. By tailored trousers, I mean trousers made in a tailored style as opposed to a jean, chino or athletic style. Such trousers don’t have to be bespoke or made-to-measure, but it is more difficult to find ready-to-wear tailored casual trousers today than it used to be.

Sean Connery wears charcoal flannel tailored trousers for golf in Goldfinger

Throughout the James Bond series, particularly from the 1960s through the 1980s, James Bond often wears tailored trousers when dressing down. These trousers are usually made by the same tailors who make his suits, in the same or a similar style to the suit trousers in the respective films. A conversation with my friends at Mason & Sons, who have made tailored clothes under the Anthony Sinclair brand (Sean Connery’s tailor) for over a decade now, inspired me to think more about smart casual trousers. They made a few pairs of wool trousers for me, in cavalry twill and plain-weave wool, that I wear both for dressing up and down.

Sean Connery wears fawn cavalry twill trousers with a black long-sleeve wool polo in Thunderball

Tailored casual trousers are the same trousers than can be worn with sports coats. They are exceedingly versatile and can be dressed up with a jacket and tie or dressed down with knitwear or sports shirts. They are not good for activewear or workwear, but they’re best in a smart casual context such as for relaxed social gatherings and restaurants.

Cloths for Casual Trousers

Roger Moore wears fawn cavalry twill trousers in For Your Eyes Only

When it comes to tailored clothing, cloth determines the formality more than anything else. Casual tailored trousers should not look like suit trousers, and that is determined by the cloths. Seasonal cloths with texture are where casual trousers excel.

Cool-weather casual trousers include woollen flannel, wool cavalry twill, wool whipcord, corduroy, heavy serge, moleskin and brushed cotton. Tweed can also work, but it often does not tailor as well as it doesn’t hold shape.

Roger Moore wears linen tailored trousers in For Your Eyes Only

Warm-weather casual trousers can be made of linen, high-twist tropical wool and fresco, wool hopsack, cotton poplin, and blends of cotton, linen and/or silk.

For the between-season trousers, wool gabardine, cotton gabardine and cotton drill can be useful. Chino cloth can also be made into tailored trousers, but it’s usually made up into a less smart style with straight outseams instead of a more tapered cut that dressier trousers have. They don’t take a crease as well and look less neat.

Cloths to Avoid

Dressy suit cloths are best avoided. In particular, smooth worsteds with little texture work unsuccessfully as casual trousers. This is usually in the form of a prunelle (a smooth twill) or a finer serge. Heavier serge with a prominent twill, however, can work well. Plain-weave worsted can go either way, but they usually look neutral enough that they dress up or down equally well.

Roger Moore dresses down his navy worsted suit trousers in Octopussy when in a bind

Worsted flannel can work as casual trousers, but it’s more of a suit cloth and will always look inferior to woollen flannel in a casual context.

Mohair’s sheen can make it look too dressy for casual trousers, but it can be good for a dressier non-suit look in hot, humid weather without a jacket. Barrathea is only for formalwear and never casual trousers.

Pinstripes and chalk stripes should always be avoided because they look like dressy business suit trousers. Solid-coloured herringbone and self stripes usually look too formal as well. Large, bold checks and windowpanes can be casual enough but they may draw too much attention down to the trousers; dressing well typicality means drawing attention up to the face and not down to the feet. Small worsted suit patterns like birdseye, nailhead and sharkskin should usually be avoided in casual trousers because they look like suit trousers.

There’s always the person who can wear some of these trousers stylishly, but it’s the exception to the rule, and they’re never the best choice.

Trouser Colour and Pattern

Sean Connery wears charcoal wool tailored trousers for his nighttime adventures in Goldfinger

These trousers can be made in any colour. No colours are off-limits, not even black or navy. Neutrals in the grey, brown, khaki and beige families are the easiest to wear, but bright colours are allowed too. Colourful corduroy and moleskin trousers are classics, but they’re not something James Bond wears. He usually sticks with neutrals except for the occasional navy.

Daniel Craig wears checked tailored trousers with a cardigan in Casino Royale

Bond doesn’t often wear patterned casual trousers, except in Casino Royale. Checks make for good trousers as long as they are small or subtle. Checks are where the worsteds that are usually exclusive for suits can work for trousers. Classic glen checks, houndstooth checks and two-and-two checks can be effective casual trousers, even though they’re suitings. Herringbone patterned trousers can look good too.

Casual Trouser Styling

The style of casual tailored trousers is more flexible than that of suit trousers, but it does not have to be different. James Bond’s tailored usually made the same style of trouser for Bond’s suits and casual dress, but sometimes they have subtle tweaks. The shape of the legs tends to be whatever is in fashion, whether it’s tapered, straight or flared. Tailored trousers almost always are pressed with a crease for a neat look.

Thunderball Black Underwater

Thunderball Black Underwater

Sean Connery swims in black wool trousers with Daks tops in Thunderball

The English style of trouser—what Bond usually wears—can have various waistband styles, with either side adjusters or belt loops. Trousers with side adjusters are not only for dressing up; side adjusters have no inherent formality, though they look neater than belted trousers. The waistband with side adjusters, either with straps and side buckles or the Daks style with buttons (traditionally a small rim-less faux smoke mother-of-pearl button) and elastic tabs, has an extended waistband with a hook and eye closure for a clean look. English belted trousers do not have the extended waistband, but they usually still have the hook and eye closure. Continental belted trousers usually have a short waistband extension with an outside button closure. There are no rules here, just customs with a lot of flexibility. The Gurkha waistband, a fussy military style that has been trendy lately, is another option.

A fishtail back for braces, however, is best saved for formal trousers unless one’s body type requires them.

Sean Connery wears grey wool trousers with frogmouth pockets casually in You Only Live Twice

Like suit trousers, the casual trousers may have on-seam or slanted side pockets, but there is more freedom here for other styles. Bond’s casual trousers in the 1960s are often dressed down with frogmouth pockets, a more casual top-access pocket designed to make the pocket easier for horseback riding. Roger Moore’s trousers often only have cash pockets (a large coin or fob pocket on each side of the front) below the waistband with no other front or side pockets for a trimmer look on screen. This pocket situation is not the most practical, especially on casual trousers that are not worn with a jacket.

Roger Moore’s tailored trousers in For Your Eyes Only only have cash pockets

Bond has worn casual trousers with one, two or no rear pockets. British trousers are commonly made with only one rear pocket on the side of the wearer’s dominant hand since that is the pocket that is used, but two rear pockets look more balanced on casual trousers where a jacket does not hide the rear of the trousers. Going without rear pockets has a more feminine look.

Roger Moore’s black tailored trousers in Moonraker have no rear pockets, though he pretends to use one earlier

Pleated, darted and flat fronts are all appropriate for casual trousers. James Bond’s casual trousers rarely have pleats outside of the late 1980s and 1990s when they were popular.

Casual trousers are often finished with top stitching down the outseam, sometimes 1/4-inch from the edge, for a more rugged look.

Sean Connery wears linen trousers in Thunderball

Trousers may have plain hems or turn-ups, and there’s no rule to determine which. Bond’s casual linen trousers in Thunderball have approximately 2-inch vents at the hem on the outseam. I do not know the purpose of these vents, though they may be there to make it easier to pass the foot through the narrow hems. These trousers are also hemmed shorter to sit above the sandals so they don’t run against the feet.

How to Wear Casual Tailored Trousers

Casual tailored trousers need more care when putting together an outfit than trousers like chinos or jeans do. Well-tailored trousers need a well-fitting shirt or piece of knitwear up top to match the elegance of the trousers.

Roger Moore’s worsted safari suit in Octopussy has properly tailored trousers

A sports shirt made of oxford, jersey or linen is a good complement to tailored trousers. Dressier sports shirts with a two-piece collar should be tucked into tailored trousers. In warm weather, a safari shirt or a camp shirt in cotton poplin, linen, silk or terry cloth can also go well with tailored trousers, and these should not be tucked if they have a straight hem. Cotton pique polo shirts are more difficult to pair with tailored trousers, but they usually look better tucked like in Dr. No. Tucking or not tucking can ultimately depend on the specific shirt, and there are always exceptions to these rules.

In cooler weather, knitwear excels with tailored trousers. A jumper over a sports shirt, a cardigan over a sports shirt (or even a t-shirt like in Casino Royale), a polo neck, or a wool or cashmere polo are perfect with tailored trousers. Wool knitwear is the easiest way to dress down tailored trousers because it complements wool trousers because it matches the smartness of the trousers while not looking like a tailored jacket is missing.

Roger Moore’s bit loafers pair perfectly with his casual trousers in The Man with the Golden Gun

The right shoes are also key to making tailored trousers work well in a casual manner. Many different kind of shoes can work, but loafers complement tailored trousers especially well in a casual way. Other shoes such as brogues, derbys and bluchers with plain toes or apron toes, monk shoes, chukka boots and Chelsea boots are easy to pair with tailored trousers. Single soles and double soles can both work with heavier trousers, while single soles often better balance summer trousers.

Dressy shoes like cap-toe and semi-brogue oxfords and wholecuts are too formal to wear in a casual manner. Very casual shoes like trainers, hiking boots and work boots do not pair well with tailored trousers because they clash with the trouser’s trim lines. Sandals, like what Sean Connery wears on occasion, and boat shoes can sometimes work with tailored trousers but are difficult to pair successfully. Espadrilles are the easiest casual summer shoes to pair with tailored summer trousers.

There are two significant downsides to wearing tailored trousers opposed to chinos and jeans: cost to purchase and cost to maintain. Tailored trousers cannot usually be machine washed, so they need to go to the dry cleaner for cleaning and pressing.

For more tips on how to dress down smart trousers, read about How to Wear Smart Casual Attire Like James Bond.

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