Winter is the time of year for wearing heavy and fluffy tailored clothes, with a focus on flannel. Autumn and winter tailored clothes are mainly interchangeable, so most of Bond’s tailored outfits that I put in the top (00)7 list for autumn can also be worn in winter, depending on the temperature outside. This list is of tailored clothes that are appropriate for the cooler half of the year in a temperate climate, and in some colder parts of the world these clothes may be appropriate for the three colder seasons of the year.
Many of these winter Bond outfits were more common in the first three decades of the series when Bond’s tailored clothes came from British tailors. Heavy cloths have largely fallen out of favour today due to modern heating, and they can sometimes look old fashioned, but they are still popular with British tailors who appreciate their drape.
1. Midnight Blue Velvet Dinner Jacket
James Bond only wears a velvet dinner jacket once in the series—on a cruise ship in Diamonds Are Forever—but it’s Bond’s only dinner jacket in the series that is exclusively for colder weather. The black or midnight blue wool barathea dinner suit is Bond’s usual choice for black tie in cooler weather, but the velvet jacket is a more iconic look for winter. Bond’s dinner jacket has one button and a self-faced shawl collar. He pairs it with midnight blue wool evening trousers with a stripe down the side. Bond dresses it down with a light blue shirt, but his usual white pleated dress shirt would be a more classic choice.
2. Grey Flannel Suit
The plain grey flannel suit, usually in dark grey, is Bond’s most common suit of the series. Though he has not worn one since Tomorrow Never Dies, it’s the ultimate suit of the classic Bond. Flannel also is the quintessential winter suit, with a soft and fuzzy finish that makes it warm, relaxed and comfortable. He wears it as either a two-piece suit or a three-piece suit, which builds on flannel’s warmth. The grey flannel suit is his first suit of the film series in Dr. No when he arrives in Jamaica. It demonstrates how he dresses on an average day for business in London, but it’s unbearably warm in Jamaica’s heat and humidity.
While the flannel suit is a menswear classic, it is not a particularly durable suit. For James Bond its status as a classic suit for the middle class businessman trumps its delicate nature, even for his rough lifestyle. Bond wears both woollen and worsted flannel suits, but in grey he chooses the classic woollen flannel variety more frequently. The fuzziness of woollen flannel accentuates the varied shades of grey twisted into the yarns.
3. Navy Flannel Suit
Bond wears plain navy flannel suits less frequently than grey flannel, but for Connery and Moore it’s a reliable cold-weather business suit. Bond’s plain navy flannel suits are made in worsted flannel rather than woollen flannel. The worsted variety milled to have a soft and fuzzy finish, but compared to woollen flannel it is sturdier and better suited for Bond’s active lifestyle.
4. Chalk Stripe Flannel Suit
The chalk stripe suit in grey or navy is Bond’s alternative to the solid flannel suit for the office, usually as a three-piece suit. The chalk stripe is reminiscent of the soft line drawn on a fabric by a tailor’s chalk. Bond often wears it throughout the first three decades of the series. Compared to the plain flannel suit, the navy chalk stripe suit can look more serious like the dark pinstripe suit, but fuzziness of the stripe makes it less formal than the sharp pinstripe.
5. Navy Doeskin Blazer
The metal-buttoned navy blazer was a Bond staple for the first four decades of the series, and his first four blazers of the series—Sean Connery’s three single-breasted blazers and George Lazenby’s double-breasted blazer—were made of wool doeskin, a type of flannel with a short nap. Unlike ordinary flannel, doeskin has a slight lustre to it. Connery’s blazer has two buttons and three patch pockets. Lazenby’s blazer has three buttons with all three to fasten and hacking pockets, an unusual but then-trendy style for a double-breasted blazer. Bond pairs the doeskin blazer with dark grey flannel trousers, matching those of his dark grey flannel suit. Bond wears a doeskin blazer in Jamaica and the Bahamas, but because doeskin is a type of flannel it is much better for the cooler half of the year such as in its later appearances in On Her Majesty’s Secret Service and Diamonds Are Forever.
6. Grey Tweed Jacket
The grey tweed jacket is not a Bondian staple, but it’s a classic winter sports coat that Bond wears a few times. Compared to the earthy brown tweed jacket of autumn, grey tweed looks more wintry. Both colours, however, are appropriate for both seasons. The first time he wears it is in the form of a grey herringbone jacket in Never Say Never Again. This jacket is one of Bond’s most classic sports coats and is detailed in a classic British manner with hacking pockets.
Roger Moore brings the grey tweed jacket into the EON Bond series in A View to a Kill, and his is plain grey tweed detailed with three patch pockets instead. Though he wears it in disguise as James St John Smythe, the jacket’s simplicity is equally appropriate for Bond. Like with the navy doeskin blazer, Bond pairs the grey tweed jacket with dark grey flannel trousers.
As an honorary mention, Pierce Brosnan’s grey windowpane tweed suit in The World Is Not Enough almost fits into this same category, but it’s a full suit.
7. Navy Overcoat
No winter tailored wardrobe is complete without an overcoat to wear over a winter suit or jacket, and the navy overcoat in heavy wool melton is the perfectly Bondian complement to any tailored winter outfit. Bond’s are usually knee-length, but sometimes the length is a little longer or shorter. Bond’s relationship with the navy overcoat started with Sean Connery in Dr. No wearing a Chesterfield coat with a fly front, but every James Bond has since worn a navy overcoat, often as a double-breasted coat in various styles. Daniel Craig continued the tradition with navy topcoats in a lighter weight and slightly shorter length to follow modern trends. The length and weight of a coat should be determined by the temperature and wind, not by fashions. Hat and gloves are optional, but they are a very practical complement to the coat.