For the famous 1983 battle of the Bonds between Roger Moore in Octopussy and Sean Connery in Never Say Never Again, both actors were outfitted by the same tailor: the legendary Douglas Hayward of 95 Mount Street in Mayfair, London.
After years of speculation, an auction at Lyon & Turnbull confirmed that Douglas Hayward tailored Sean Connery for his 1983 return to the role of James Bond in Never Say Never Again. They sold his cream suit (with two jackets) from the film on 23 June 2021 for £5,250. The trousers have a label with a production date of 21.7.82, which means it was made at the right time for Never Say Never Again. The auction listing incorrectly states that it was made for Connery’s 1982 film Five Days One Summer, which was filmed in 1981 according to IMDB Trivia.
Hayward tailored three different actors for Bond: Roger Moore for For Your Eyes Only, Octopussy and A View to a Kill, Sean Connery for Never Say Never Again, and Peter Sellers for Casino Royale. Hayward is the most famous London tailor to have outfitted Bond, and he’s also tailored more actors to play Bond than anyone else has, even if two of the films he made for were not part of the EON Productions Bond series.
When Roger Moore’s Bond arrives in India in Octopussy, he is wearing a tan lightweight cotton suit. When Sean Connery’s Bond arrives in the Bahamas in Never Say Never Again, he is wearing a cream tropical wool suit with a slightly more formal look. The suits are variations on the same theme—lightweight and in the same colour family. Tan perfectly balances Moore’s warm complexion, while cream (bordering on a pale beige) helps Connery’s deep tanned complexion glow. Wool drapes better than cotton and tailors better, so Connery’s suit looks a bit neater than Moore’s. Cotton may feel cooler against the skin in hot weather, but lightweight open-weave wool ultimately breathes better.
Both suits have the same cut and style. The jackets are tailored with soft shoulders, gently roped sleeve heads, a clean chest and a suppressed waist. Because the shoulders have only light structure, the jacket takes on the shape of the man wearing it. Both Moore and Connery had large builds, but Connery’s shape was more athletic whilst Moore’s was boxier. The cut of the suit accentuates each man’s build. The roped sleeve heads help Moore by giving more definition to his silhouette, which Connery already has.
Both suit jackets are made in a button-two style in a low stance and have medium-width notched lapels with a straight, high and shallow gorge. The jackets are detailed with flared double vents, straight hip pockets with flaps, and three buttons on each cuff. The jackets have light-toned horn buttons to match the suits.
The trousers have a similar style with belt loops and a medium-width straight leg with plain hems. Connery’s trousers have a slightly more classic cut with extra fullness in the upper thigh than Moore’s have. Connery’s trousers may have a slightly lower rise, ultimately owing to a different body shape than Moore’s. Connery’s trousers also have a more traditional pocket style, with slanted side pockets and one rear jetted pocket. Though the tops of Moore’s trousers are unseen with this suit, his Hayward trousers ordinarily were made with no side pockets, a cash pocket below the waistband on each side of the front, and two rear jetted pockets.
The way they accessorise their suits is much different than the suits themselves. Moore’s shirt from Frank Foster is an airy white cotton voile with a high long-point semi-spread collar, a front placket and one-button cuffs with large buttons. Sean Connery’s Turnbull & Asser shirt is periwinkle cotton poplin and has a more classically proportioned semi-spread collar—which is likely his own version of the Classic T&A Collar—a front placket and single-button button-down cocktail cuffs. Moore’s shirt is lighter in colour than his suit whilst Connery’s shirt is darker than his suit, and these colour contrasts are what primarily differ these two outfits. Moore’s shirt is neutral to take advantage of how the tan suit flatters Moore’s warm complexion. Connery’s shirt brings a little coolness and contrast to the look to flatter his cooler complexion.
Moore’s tie matches his suit with tan and brown stripes to play up the warmth of the suit’s colour. Connery, on the other hand, wears a light grey textured tie with thin, wide-spaced blue stripes, which coordinate with the shirt’s cool theme. Moore’s tie is made with a four-in-hand knot while Connery’s is made with a Windsor knot, matching their personal preferences.
Both Moore and Connery wear a brown belt and brown shoes. Moore’s shoes are his usual loafers. If Connery’s shoes shown under his bed in a later scene are the same as what he wears with this suit, they are mid-brown three-eyelet derby shoes with a moccasin toe. So they both wears shoes with moccasin toes.
Overall, Connery’s outfit has a more classic look, and a slightly dressier look. It brings back the cream suit idea from Diamonds Are Forever over a decade earlier and does it considerably better. The suit in Never Say Never Again fits much better than his previous cream suit as Bond, it has lapels in a timeless medium width, and the wide and short pink tie is replaced with a classic tie in cool colours. It makes up for Connery’s most-maligned suit of the series.
Roger Moore’s suit is a reliable choice for the heat, but it doesn’t look as neat as Connery’s does. His outfit has a classic Moore-Bond look, which breaks away from the older Connery style but looks superb on Moore. The Hayward cut works well for both men, and neither suit looks particularly dated today.
If I had to pick a winner between the battle of the Bonds as far as these two tropical suits are concerned, I prefer Connery’s suit for its neater drape and I prefer the outfit overall for the shirt’s blue colour. Moore’s shirt in cotton voile, however, wins for practicality and for the drama of the higher collar. I think Connery’s grey tie clashes a little with the cream suit (though grey and cream can work well together in certain contexts) and does not have enough contrast with the shirt. I would have put him in his classic navy grenadine tie from his older Bond films. Moore’s tie, while not to my personal taste, works perfectly with his outfit.
If I’m considering the wardrobes of the two films overall, I prefer Moore’s for the striped grey three-piece suit in the London scenes. Ultimately, the wardrobes of each film work well for the respective actors and any preference for one over the other is a matter of personal taste.