Octopussy vs Never Say Never Again: Tropical Suits Made by the Same Tailor

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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.

26 COMMENTS

  1. Connery doesn’t appear to have a high contrast complexion in these pictures. Am I wrong here? Is it lighting? I mean I have always considered myself a pretty medium contrast, but if I had to come down on one side or the other I’d say I lean towards low as opposed to high. I can handle a decent amount of contrast, but a midnight grenadine tie, paired with my mid grey sharkskin suit and a white or light blue shirt does overpower me a bit. Connery’s hair seems lighter than man and his skin darker. He doesn’t appear to be a winter here to me, although I fully admit I don’t have a perfect understanding of contrast and complexion. What are your thoughts Matt?

    • Connery’s deep tan is what gives him that winter complexion. Putting an unnaturally coloured hairpiece on him isn’t going to change his complexion. His complexion looks good with high-contrast clothing to make him look his best.

      • Yeah I think it is safe to say I don’t have a full understanding of complexion and contrast. I would have thought someone with black hair and pale skin, for example like Tyrone Power in Flusser’s Dressing the Man, would be a winter. His complexion appears significantly different from Connery’s here.

        The biggest differences I have seen attempting to incorporate contrast and complexion myself is that I look much better in blue dress shirts. In addition to the fact I have blue eyes and blue shirts noticeably help there, they also don’t drain color from my face the way a white shirt does. Also I have found very dark ties distract from my face.

      • Connery’s hair was dyed on the sides a light-mid brown color to hide his then greying hair and to match the light-mid hairpiece on top, except for the sideburns that were left uncolored and are silver. Connery’s hair was dark brown originally obviously. I have always thought the color didn’t look great on Connery, but I wasn’t the hair and make up person on the film. Connery look great at 52 and his face had taken on a furrowed, rugged and mature look that continued unchanged until his retirement from films. Hayward tailored both Moore and Connery very well. Hayward had the eye for proportion and his cut is as timeless as it is elegant. I’d wear that cut now and be proud to wear it to work or personal. I don’t think you can really go wrong, Maybe a slightly higher button stance for me but I would change a lot.

    • If you’re looking to understand complexions and colours more I really recommend the book “Color for Men” by Carole Jackson, which I’m 99% sure I found because I think Matt recommended on this blog at some point. It’s quite cheap on Amazon and it’s very clear. I always thought I was a winter but reading the book I learned I’m a summer, and I look far better in my clothes now for it.

      In some small ways it’s a little outdated but only in its presentation (published in 1984), and the good thing is that by its very nature it’s more about finding style rather than following fashion; ie wearing colours that actually suit you, proper proportions for your body shape, avoiding fads that will disappear in ten years etc. Everything this blog stands for.

      • Yes, this is the book I learned from. It’s much clearer than what Alan Flusser describes for how to dress a complexion in Dressing the Man.

      • I was a bit confused reading Flusser’s book section on color, and I have read that section many times. Many of the examples he uses aren’t striking, and really maybe 1 of the examples has a complexion that resembles mine a little bit. I will certainly consider the book Color For Men. Thanks!

  2. It is our good luck that the year Moore and Connery could go head to head sartorially was one where traditional cuts were back in style. It makes it much easier to do comparisons like this. Both suits look great, but I forgot how low the jacket buttons were during this period. Are the buttons actually placed lower down on the jacket than in the sixties?

  3. Let’s face it, in a suit-off between Sir Sean & Sir Roger one would rather expect the latter to have a head start – being the more inherently dapper of the pair, though heaven knows that Sir Sean wore a suit well – so it’s quite impressive that they seem to be just about neck & neck in this particular contest (though I agree that Sir Roger’s tie loses points for being quite elegant, but just not very Bond; a colder colour would have lent that hint of danger that should attach to all 007 sartorial choices).

    If I may divulge a Deep, DARK secret – my favourite suit in these pictures is actually the one worn by Mr Rowan Atkinson (It’s not at all Bond, but it is quite tasteful and I enjoy the bold contrast of that very dark tie).

    • ED, I rather like that suit too. 4×1 double breasted isn’t very Bond-like, but it looks nice on him and works for the character, who is very obviously British and sticks out from everyone else around him. Many double breasted suits from that year, and especially later in the decade, have not dated very well.

      • I agree, the double breasted suit looks stunning. I wonder if Hayward did it too ; it looks pretty well cut, at least on the current picture. It gives Atkinson more presence, especially since he is standing next to Sean Connery, no else !

  4. Interesting to note that the shoulders of the two suits are both roped in the same way, while sometimes Moore’s Hayward suits have shoulders that are roped but in a sort of outward way (like the grey 3-piece in Octopussy). I wonder why, I guess Moore and Connery’s shoulders are probably of different shape and thus needed a different kind of roping.
    Otherwise both suits are very flattering to both men’s physique, and to me it’s a tie (ha !). I like the light brown combination on Moore here, I think it suits his complexion perfectly and it’s also completely appropriate given the location. I like the striped tie too, just not a big fan of moccasins with a suit.
    Connery looks great as well, and is probably in better shape, but I agree that the silver tie clashes a bit with a cream suit. Also the suit looks a tad too yellowish to me. With such a tan he had, they could have made him wear a light grey suit just like the mohair suit in Dr No or something similar to what Moore wore in Live and Let Die. But clearly it’s Connery’s best suit In NSNA. His other looks are often a bit bland and they used too much grey to my taste (not in a sophisticated variations like in FRWL but often with grey on grey combinations).

  5. I agree with Ryan that the cut and proportions for both suits are superb. I would also wear this today instead of the rubbish which has dominated in recent years with the high button stance, low rise trousers and an extremely high gorge in some cases.

    Also nice to see a cream suit in wool which isn´t quite easy to find nowadays compared to cotton and linen for lighter colors.

    It sounds like many readers here dislike the others suits in NSNA, but I mostly like them besides the Windsor knot. I´m not so fond of the casual clothing or the movie itself though. Finally it always amazes me how good Connery looks here compared to Diamonds are Forever.

  6. Excellent article, and I enjoyed your book, Matt!

    Anyone skilled enough with Photoshop to swap in the DAF toupee or some such? The hairpiece somehow makes Connery look like not the same character to me… but maybe that’s just me.

  7. I’m curious, on the second jacket they say there’s a small red ribbon to the lapel, anybody have any idea how that would’ve been incorporated into the filming? I don’t see that in the final film. Maybe added after the movie for personal use or another production?

    • I’m guessing the ribbon is merely a sticker attached to the lapel as a marker to differentiate one jacket from the other. I don’t think it’s meant to be worn with it on.

      • Thanks, that makes sense. I’ll investigate more when it arrives here in Florida, I was the lucky winner :) I also won the other grey Connery suit from that same auction which is not from “The Untouchables” like they say as that’s an American production and this suit has English labels inside, you might want to take another look at that as I think you may recognize it! (Wink Wink).

      • Congratulations on winning the suits! I think you got quite the deal on them.

        I have not been able to place the grey suit. It is very similar to the dark grey suit from Never Say Never Again, but it’s not a perfect match because it lacks vents and has different lapels.

    • Congrats on getting the winning bid. I had a max bid of GBP 1100 for the NSNA suit, but that turned out to only be the opening bid! I had hoped to make a bargain, but the market manifested itself as usual.

      S

  8. I find that the shirt and tie totally undermine Connery’s otherwise lovely suit. The shirt looks a little purple in some lights, almost like it’s toeing into lilac territory, and it’s an odd choice (then again, I find that shirts darker than suits almost never work, and usually make someone look like a villain). The tie, in turn, has too little contrast with the shirt and appears to violate the unwritten rule that a tie should almost always be darker than the accompanying shirt.

    All together, it makes Connery look odd and like an ill-dressed tourist, despite the good suit. Moore’s outfit, while more casual in colour, appears much better coordinated and put-together, which gives him, in my eyes, a more serious and businesslike appearance, despite his palette saying otherwise. That, and despite being similar heights, I find the somewhat low button stance flatters Moore more than it does Connery, who appears shorter and less physically impressive than he was that way.

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