Poll: Which Tailor Dressed Roger Moore Best?

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While Sean Connery had the consistency of being dressed by Anthony Sinclair for all six of his James Bond films, Roger Moore was fitted by three different tailors over his seven Bond films. Cyril Castle, Roger Moore’s tailor throughout The Saint and The Persuaders, dressed Moore for his first two Bond films, Live and Let Die and The Man with the Golden Gun. Italian tailor Angelo Vitucci of Angelo Roma dressed Moore for The Spy Who Loved Me and Moonraker. The famous Douglas Hayward came in to dress Moore for his three 1980s Bond films: For Your Eyes Only, Octopussy and A View to a Kill, and Hayward went on to dress Moore until the former passed away in 2008. Moore’s three tailors each gave him a unique look, from the ultimate in fashion to understated elegance. Vote at the end of the article for who you think dressed Moore best.

Cyril Castle

Cyril Castle was a neighbour of Connery’s tailor Anthony Sinclair on Conduit Street, though his cut was more flamboyant and focused on fashion trends. Building on the first major* foray into fashion Bond took in On Her Majesty’s Secret Service, Castle dressed Moore in tailored clothes that took hints from the fashions of the early 1970s. He introduced Bond to flared suit trousers, though they are more of a subtle bootcut than a bold flared leg. The lapels are of a classic width in Live and Let Die but widened to a trendier width in The Man with the Golden Gun. Castle also introduced the double-breasted suit to Bond, though George Lazenby previously wore a double-breasted blazer.

Though Castle cut a jacket in the English tradition for Moore with soft shoulders and a full chest, the small details also fascinated Castle. The cuffs of most of the jackets are notable for their flared shape with a kissing link fastening. The silk ivory jacket in The Man with the Golden Gun dispensed with the link cuffs for gauntlet (turnback) cuffs, a classic Edwardian detail that also featured on Connery’s early dinner jackets. The English details were important to Castle, and they also included deep double vents and slanted hip pockets.

Castle mostly made clothes for Moore in the classic Bondian blues and greys but also included brown, black and olive suits. Connery had previously worn the first two of those three. Castle more prominently used some of the flashier fabrics that Connery wore on occasion in his Bond films, such as mohair and silk.

Angelo Roma

Angelo Roma is the tailor Roger Moore is more usually associated with due to the bold 1970s look he gave Moore. House owner Angelo Vitucci’s suits are beautifully cut in the Roman style with straight shoulders and an elegant clean cut. For The Spy Who Loved Me, Vitucci widened the already wide lapels that Moore previously wore in The Man with the Golden Gun, and he also widened the flared trouser legs for an update look.

The details of Vitucci’s clothes included flapped breast pockets on some of the sportier jackets and front-pocket-less trousers. But he normalised the jackets an ordinary four-button cuff and used a regular width for the pocket flaps so not to overwhelm the front beyond the oversized lapels.

Vitucci dressed Moore in one blue suit and one grey suit in Moonraker, but his most infamous suit for Moore is a rich brown silk suit in The Spy Who Loved Me. Though the colour could not be more flattering to Moore’s warm complexion, and it’s worn appropriately in the Mediterranean, the shade of brown is unfortunately most associated with 1970s fashions. Vitucci also modernised Moore’s blazers with four-hole metal buttons rather than the more traditional shanked style. Following Bond tradition, Vitucci used silver-toned metal rather than yellow-toned metal, except on the double-breasted blazer in Moonraker.

Though Vitucci’s look was only featured in two films, Moore will forever be notoriously remembered for wearing these fashionable 1970s clothes, despite the many positive traits of these clothes.

Douglas Hayward

Douglas Hayward is the most famous of Roger Moore’s three Bond tailors for his work on many films beyond the Bond series and celebrity clients such as Michael Caine and Terence Stamp. Of Moore’s three tailors, Hayward gave Moore the most classic style appropriate for the 1980s without worrying too much about 1980s fashions. Hayward brought back a more traditional English air to Bond, with soft shoulders punctuated by roped sleeve heads. Hayward narrowed the lapels for For Your Eyes Only, and then even more for Octopussy so they were back down to a balanced, timeless width. The trousers no longer were flared but featured a straight leg, which also got narrower from For Your Eyes Only to Octopussy.

Whilst Hayward was not into gimmicks, his jackets feature a very low button stance that was a hallmark of 1980s and early 1990s tailoring. Apart from this, the suits would not look at all dated today.

Hayward tailored suits mostly in blue and grey flannel solids and chalk stripes for city wear along with an appropriate tan or light brown gabardine suit for the sunnier locales in each film. For evening wear, Hayward tailored beautiful dinner jackets in black and midnight blue wool and ivory linen, with either peaked or notched lapels. He also gave Moore a variety of navy blazers and understated tweed sports coats for more informal occasions.

Each of Moore’s three tailors offered the Bond films something special. Cyril Castle brought a unique creativity to Bond’s tailored wardrobe. Angelo Roma made Bond look current, and despite the clothes being some of the most dated in the series, they still look fantastic on Moore. Douglas Hayward returned Bond’s wardrobe to the classic elegance that defined Sean Connery’s Bond wardrobe, but he did it in a way that was appropriate for an older Moore. Which approach do you like best?

Which tailor dressed Roger Moore best?

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37 COMMENTS

  1. I like something about all of Moore’s Bond tailors, but Douglas Hayward’s understated style has to win out for me. Hayward made his blazer’s dressier then Anthony Sinclair with straight flapped pockets contrasting with Sinclair’s open patch pockets. Cyril Castle and Roma did slanted flapped pockets on there blazers.

  2. I have gone with Hayward but I’ve never liked that almost transparent shirt he wears in Octopussy with the Ivory dinner jacket, and as you stated, the button stances are distractingly low. I also think some of the jackets could’ve been taken in at the waist and little more – Angelo’s fit the best but the details, lapels and colours date the clothes too much. Hayward did away with that. My dream choice would be the details of Douglas Hayward but with the fit of Angelo Roma.

    • That shirt was made by Frank Foster, Hayward was only responsible for the dinner jacket and trousers. Voile is indeed very transparent, but it breathes better than poplin shirting would during an Indian summer.

  3. I voted for Douglas Hayward because I have one problem with some of the Cyril Castle suits.
    Sometimes I find that Castle’s jackets give Moore’s upper torso a somewhat barrel shaped look (I don’t know how to describe it better).
    The look I mean seems to be more evident in The Saint outfits but it is also sometimes visible in the Bond movies.
    I love Castle’s creations like the navy blue suit and overcoat in Live and Let Die and the grey silk suit that Moore wears when arriving in Hong Kong in the man with the golden gun.

  4. Though it’s far from his best film, I’ve always thought that Moore looks all around at his best in The Man With The Golden Gun, so I’ll go with Castle, though I respect and admire the Hayward suits as well. Angelo’s, while some of the best-fitting of the entire series, are just too fashion-forward to be timeless which places his contributions beneath the other two for me.
    Happy New Year to all!

  5. All three tailors have something to recommend them (obviously!) but if fit is paramount, I might argue that the much-maligned Angelo suits fit best of all.

  6. All three are great. Especially if you think for a second how much better Moore is dressed compared to Daniel Craig.
    I went with Angelo Roma, because his suits have the most beautiful shoulder line of the 3 tailors.

  7. This was a hard one! Everything Moore wore as Bond is admirable in terms of top quality tailoring although I have to say that in terms of fit the Angelo suits are as close to flawless as can be. Yes, the lapels are wide and the trousers are too flared but the fit of the suits more than make up for it. I think the stronger shoulders and overall slim cut compliments Moore’s body extremely well. The Cyril Castle suits are a VERY close second for me and the fit is flawless and the details are more Classic. The only reason I think the Angelo suits are better is because of the shoulders. The softer and narrower shoulders of the Castle suits doesnt build Moore up the way the Angelo suits does, however they are still better on him than the Hayward shoulders, I think. Hayward’s suits are absolutely fantastic but someone had to be number three and what places the Haward suits the lowest for me is the narrow shoulders and the low button stance. To me it doesnt flatter Moore’s specific body as well as the other suits. The narrow shoulders takes away from the V-shape of Moore’s torso and coupled with the low button stance it makes his upper body look a bit straight and shapeless. I also feel the suitings and styles of the 80’s where a bit less creative and interesting than in Moore’s earlier films. But this is really nit-picking and one cannot deny that all three examples are the best of the best in terms of tailoring and style. I wonder if we will ever see this again in a Bond film…

  8. Moore’s Hayward suits weren’t as shaped at the waist as the suits from Castle or Roma. This may have been done deliberately as Moore was now well in his 50’s and not as trim in the waist as he had been a few years before. Hayward probably thought it would be more flattering on Moore at the time.

  9. Hayward’s suits would be perfect if they had the button stance of Castle and shoulders of Roma. AS everyone is saying, it’s really hard to pick. In the end I’ve gone with Cyril Castle, as his fashion elements are least offensive to my eyes. I’m not fond of flared trousers, but I’ll take them over Hayward’s very low button stance, but only barely.

    The truth of the matter is I would happily wear a suit from any of these tailors without hesitation.

  10. I want to echo the majority opinion on this subject. It is hard to choose a favorite among these tailors. I was in high school at the time of Moore’s 80s-era Bond films and was just noticing men’s tailored clothing then. So, the Hayward suits have long been the most recognizable, or natural-looking, to me. But I find the low button stance more and more distasteful. Moreover, when I compare the Hayward clothes to the beautiful shape of the Vitucci/Roma suits and jackets, I have to pick the latter. I could not tolerate the flared pant legs, but I could stomach the wide lapels and would be delighted with the colors, if only I could wear such beautifully-cut clothes.

  11. I went with Hayward, but if the question had been phrased differently – i.e. which taikor’s suits fit the best – I would have picked Angelo. Fit is of course very important, but it doesn’t exist in isolation. Hayward’s tailoring, while not exactly to my taste, is the most balanced in terms of fit and fashion.

  12. All three suits are uniquely crafted my master tailors, I would have no issue wearing any suit from Castle, Roma, and Hayward. However, I had to chose Roma over Castle and Hayward. On Hayward’s suits the button stance is extremely low which is something I really don’t like. Castle’s suits are a little fashion forward for me just like Craig’s fashion forward suits on Skyfall and Spectre. Too me Roma is a great in between and the fit is perfect. The structured fit of Roma’s suits is very flattering to Moore. My issue with Roma is that the lapels are too wide but that was the style at the time. The same could be said about the extremely low button stance on the Hayward suits.

    On a side note, I would like to wish all the readers a very Happy New Year! I can’t wait for more of Matt’s post in the upcoming months.

  13. Personally, for me, Hayward comes out on top. His house style just looked so, almost effortlessly, elegantly executed. I think both Castle and Vitucci have their pluses. The latter seems to be dismissed because of fashionable touches like flared trousers and wider than average lapels but his cut and balance overall is exemplary. Would that I would see suits cut as superbly nowadays but we can but hope that when this lousy current trend passes and if suits are worn at all KN a few years time that such proportion and balance might again be witnessed. Castle seems to hit somewhere in the middle. His suits for Bond have little to fault them and I love the unique narrow wrap of his DB suits, for example. It’s all good and this is why Moore’s wardrobe became my personal template for refinement, good taste and the model to aspire to for over 30 years now! Btw, Happy Birthday, Matt

  14. Happy birthday Matt, and thanks for such a great blog. I have almost as many new suits- mostly off the peg, admittedly (but including some in shades of brown!)- as the months I have been checking in. I now believe I’m due a tailor-made dinner jacket!!

    I’m a James Bond fan, but I no longer return here so much for the JB connection as for your attention to detail and your very obvious and infectious passion. I hope you continue what you do and find ever more resources to mine in our favourite series.

  15. I voted Hayward. I think a lot of the button stance that people refer to is down to the fashion at the time.

    Did he use Frank Foster for his shirts throughout this time? BTW the gossamer thin Dress shirt he wears is faboulous. I had Frank make me one some years ago. It’s a truly beautiful thing to wear.

  16. It’s interesting how the lower button stance of the 1980’s has become the main focus of the Hayward suits which are otherwise, almost universally admired. Again, as with the criticism of 1970’s features, it seems that it’s a psychological reaction to something which is now remote from current fashion. The thing is though, it’s the current button position (with the top button of a 2 button suit sitting almost close to the sternum) which is far removed from the classic positioning rather than the low button stance which, although lower than what would be considered absolutely classic, at least has the merit of a clean line between jacket and trouser waist. Something you yourself have pointed out many times before here.

    • If I had to choose between a Hayward suit and a currently fashionable suit I would choose Hayward in a heartbeat, but I still think a slightly higher button stance (like Angelo’s or Castle’s) keeps the tie from flopping around and is more forgiving to a slight paunch. But we are splitting hairs here – any of the 3 suits are far superior to anything Bond has worn in a long time.

    • I understand what you mean David and I agree that its sometimes easy to unintentionally fall into the trap of judging something based on the current state of things, simply because we lack distance to it. However, I personally detest the high button stance of today’s suits and for me and my body type I think a classic to lower button stance works very well roportionally. With Sir Roger though I feel that it does make the proportions slightly uneven (with emphasis on the word slightly since, as Dan points out, we are truly splitting hairs here). Haywards suits are absolutely stunning and are some of the best tailored clothes ever put on screen by anyone wearing them, be it Sir Roger och Michal Caine or anyone else. I just think that the low button stance doesn’t work so well on Moore specifically, not that there is anything wrong with coats cut with a lower button stance in and of themselfes. And its of course my own personal view, comparing the various suits Moore has worn by different tailors.

  17. Hayward gets my vote on the basis of the grey chalk stripe and navy double-breasted suits in Octopussy, although the latter is far too briefly seen.

  18. Angelo fitted Moore best.

    If you consider the three suits in grey side by side Moore looks best in the Angelo suit.

    Yes they are of their time, but so are all clothes.

    All great tailors, beautiful clothes, but if one modified some of the more flamboyant features of the cut, then we are left with Moore in a beautiful fitting suit that exudes style.

    A little panache is not a bad thing and is in keeping with the Bond character, who was not always conventional. All three tailors certainly beat the suits of Craig, which make him look like a second rate estate agent.

  19. I agree to your observation. I myself prefer Castle on the whole but your remarks about Angelo concerning fit are correct. Hayward’s suits for Moore in FYE show slight fit problems – especially around the waist (the grey flannel suit therefore looks a bit sloppy IMO).

  20. I much prefer Cyril Castle and Douglas Hayward over Angelo Vittuci. Anything within the distinctive range of an English cut would flatter the type of character Bond is. However, I can see Moore in odd jackets and sport coats from Vittuci, though the trousers are notwithstanding.

  21. Here I go again making suggestions. …

    What’s appropriate to wear when going through an airport? I myself still wear a suit even if I’m sitting in economy. I did get a free upgrade once and access to the lounge which was great.

    Is a rolling luggage bond like?

    • If you wear a suit when flying, a softer one is the best choice.

      Rolling luggage is not Bond-like, but if your luggage is too heavy to carry yourself and you don’t have someone to carry it for you, wheels are a practical innovation not even Q could think of.

  22. When wearing a v neck collar, should the shirt collar be in or out? What does it say if you wear it one way or the other?

    • If you’re wearing a tie, the collar should be inside the jumper’s collar. If you’re wearing the shirt collar open, it can go either way, so long as it doesn’t the collar doesn’t look forced inside. Different shirt collars and different size V-necks can make a big difference. It doesn’t say anything either way you wear it.

  23. Hayward 80s cut didn’t do it for me. The button stance and gorge etc. The too clean chest. I don’t think they were flattering on Moore. The 60s style for Thomas Crown looked more “classic” (jacket and trousers). The Cyril Castle cut on Moore for his Bond films were very complimentary in my opinion.
    Cheers.

  24. Speaking about tailoring have you ever compared Mr mason’s off the peg 007 suit to the bespoke 007 suit? I spoke to him about it and he basically said the main differences are half canvass and full canvass. Your thoughts?

    • You can get full-canvas with Mason’s Special Order suits, as well as change many things about them. But only with bespoke can you get a suit exactly like Connery’s, with a fuller chest and button-tab side adjusters. The make of bespoke will be better than Special Order with full canvas, and the fit will be even better.

    • That would be a vote for Cyril Castle! Castle cut the clothes in his own unique style for The Persuaders, while Moore picked out the cloths and chose details for the suits.

  25. I have just watched a Commentary on The Man with the Golden Gun (iTunes download – extras). Here Sir Roger Moore says that the suits in this Bond film is made by Angelo…

    • I’ve heard the commentary, but Moore remembered incorrectly. One of the Cyril Castle suits from the film was sold at Christie’s a few years ago, which proves it beyond just seeing that the suits in The Man with the Golden Gun have Castle’s very distinctive cut and style.

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