Learning from Bond: A Checked Jacket and Flannel Trousers


I almost always think about James Bond when I purchase clothes and when I put them on, but I like to put my own spin on how I compose my outfits. Every part of my outfit pictured here is inspired by James Bond, but it does not directly copy any James Bond look. The mostly monochrome outfit consists of a black and cream checked jacket, grey flannel trousers, a white shirt, a grey tie and brown chukka boots.

The jacket is a vintage find from the 1980s. It does not have a brand label inside, but I think it may be from Paul Stuart. The cloth is 50% silk and 50% wool, and it has a bold black and cream plaid that is larger than a Glen Urqhart check. Overall the jacket reads as mid grey. I got it because it reminded me of Roger Moore’s bold checked jacket in The Man with the Golden Gun, and it also reminded me of some jackets that Pierce Brosnan wears in Remington Steele, another significant style influence for me. The jacket has a button-two front, flap pockets and long double vents. The gorge is slightly lower than on a modern jacket, but it looks classic.

The trousers are medium-dark grey flannels from Niven Tailors. They have frogmouth pockets, which were influenced by Sean Connery’s frogmouth-pocket trousers in Goldfinger and You Only Live Twice. The grey flannel was inspired by the trousers that Connery wears with his blazers in Thunderball and Diamonds Are Forever. Instead of Connery’s Daks tops, these trousers have slide-buckle side adjusters inspired by Daniel Craig’s Tom Ford suit trousers. I find that this kind of support functions better. The trousers have a narrow straight leg like George Lazenby’s trousers in On Her Majesty’s Secret Service have.

I went with a low-contrast jacket and trouser combination like Sean Connery often wears as Bond. Overall, my trousers look a little darker than the jacket, so there’s that contrast. The contrast in the perceived shade of the jacket’s grey and the shade of the trousers’ grey varies depending on the light, and in lower light there is surprisingly more contrast. The main contrast between the two is in pattern and texture. The jacket has a bold pattern and a little sheen, whilst the trousers are solid with a nap. The two fabrics are very different, but they play well together because both are in medium-weight cloths.

The low contrast and monochrome look of Sean Connery’s hacking jacket and cavalry twill trousers in Goldfinger served as the primary concept behind my outfit

The white cotton poplin shirt is from Turnbull & Asser and is a bespoke shirt sample that I won in a contest sponsored by HandCut Radio and Thomas Mason. The shirt has a larger variation on their Prince of Wales spread collar, which was inspired by Pierce Brosnan’s collar in Tomorrow Never Dies, and the new ‘1962’ cocktail cuff that Turnbull & Asser recently developed based on the one that Connery wore in the Bond films. More on this shirt will be coming at a later date.

The grey tie with a grey jacket and trousers was inspired by how Bond wears grey ties with his grey suits with grey ties in For Your Eyes Only, Skyfall and Spectre. This grey tie in particular is a bespoke grey grenadine from Sam Hober. The grenadine tie is a Connery Bond staple and is a staple of my wardrobe with over 30 examples. Bond wears a grey grenadine tie such as this in For Your Eyes Only and Never Say Never Again, though I only had the former film in mind when I got the tie. The tie is untipped, like in the early Connery films.

The colour palette of this outfit from Skyfall was the main inspiration for the colour pairings in my outfit.

With a grey tie and trousers, a jacket that reads as grey, and a white shirt, the outfit looks monochromatic. Daniel Craig’s similarly monochromatic and low-contrast suited looks in Skyfall and Spectre were some of my main inspirations here, but Sean Connery’s all-blue outfits in From Russia With Love and You Only Live Twice, and his all-brown outfits in Goldfinger and Thunderball originally turned me on to the single-coloured looks. I particularly like Craig’s low-contrast monochrome looks because they look good on my low-contrast complexion. My colouring is similar to Craig’s.

The traditionalist in me wanted to wear black shoes, as that’s what Bond would have worn and they would have kept the outfit entirely monochrome. But I went with brown footwear because I knew I was going to be outdoors in a park, and I wanted brown boots to dress down the look just a little. The boots are the Crockett & Jones ‘Tetbury’ chukka boot in brown leather, which Daniel Craig wears in black in Skyfall. If I could make a change to this outfit, I think that my tobacco suede chukka boots would have worked even better. Black ‘Tetbury’ chukkas like Daniel Craig’s might have been the best for this outfit. I do not own any black shoes that could have dressed down this outfit in the way I wanted to.

The outfit is finished with a white folded linen pocket square, inspired by Sean Connery’s Bond in Dr. No and From Russia with Love. Daniel Craig’s white pocket squares may have been in the back of my mind as well, but like Connery’s, mine does not match my shirt.


  1. This outfit is great, I love such a low contrast matching, it is tasty and elegant. A true application of Bond style, not a copy. Cut and volumes are classic, maybe slightly on the large side, but still nice

    • Thanks! Indeed, the low armholes are a classic sign of ready to wear. But it has full canvas construction, so it’s already on the higher end of ready to wear.

  2. Looks great overall. How do you feel about the length of the jacket? It seems an inch or so too long.

    • I think the length is spot on, and it is perfect by the traditional standards. It just covers my seat and is approximately half the length of my body from the neck down.

    • It’s interesting, I had a conversation with a customer about this the other day. He wanted a traditional length jacket, but his wife wanted something more “European”. I split the difference and made sure it still just covered his rear. Oddly, “European” would have been shorthand for the baggy style suits that were fashionable 25 years ago…

  3. I agree, a great outfit. Also think that jacket is spot on lengthwise, and the trouser fit looks great, if you told me you were 6 foot tall I’d believe it based on that bottom photo. I’m considering a glen check sport coat like that, maybe not a quite as bold a pattern, but in a similar mid gray overall effect. What other trousers would you pair with that jacket?

    • Thanks! That’s the power of well-proportioned clothes and good photography angles!

      With a more subtle black and white glen check jacket, charcoal trousers work well.

  4. A lovely outfit and the jacket length is perfect – it helps you look taller without being ridiculously short. I understand the sort of monochromatic look you are going for, but for my money a red or rust overplaid or windowpane check would have added a little interest to the outfit.

  5. Matt— this is a terrific look! Before I started reading, I noticed the cut of the jacket. The width of the lapels looks modern enough though. A timeless look. The contrast with trousers works well. Beautifully done, palette in grey.

  6. I actually prefer a medium height gorge, like this or just slightly higher. The shirt collar fits neatly into the open space and lines up with the notches. The problem with having the gorge so high that it crawls practically over the shoulder is you end up either ignoring collar alignment completely (like the Skyfall still above) or having to wear one of those extreme wide collars which show about two inches of tie length on either side of the knot. Great colour choices too.

    • I agree, this gorge looks just about right. It avoids the extremes of the 80s (too low) and present (too high).

  7. Nice outfit ! I especially like your new collar proportions and the jacket’s gorge, very classic, reminds me of the TWINE shirt and suit proportions. I have a very similar vintage sports coat, do you think it would work with mid grey or mid brown cavalry twill trousers as well ?

    • I think this cavalry twill trousers in either colour could work well depending on the exact colours of the jacket. With my jacket here, it has a warmth that goes well with my tan cavalry twill trousers. Grey trousers need to be a least a little darker than mid grey, as these are, or charcoal.

  8. Wonderful outfit. Very elegant. How are Sam Hober grenadine ties? I like grenadine, but most grenadine ties are rather heavy and the knot comes out bulky. I’d like to buy a lightweight grenadine tie with very light interlining that would make it possible to create a small elegant knot. Yours looks fine.

    • Sam Hober use real grenadine silk and make very fine ties. The ties are bespoke, so if you want one with a very light interlining like Connery’s, they can do it. I asked them to make the neck area of the knot a little narrower than usual so the knot will be shorter, but no less thick.

    • I’ll second Matt’s assessment of the Hober ties. If you’re wanting a trimmer knot in a grenadine, I’d recommend the fina/piccola grenadines instead of the grossa. They seem to make a somewhat smaller knot. Their grenadines are truly lovely (as are their other materials… I particularly enjoy the mulberrywood weave and shantung). Their pocket square selection is spectacular. Great folks to work with, too!

      Great. Now I want to go order more stuff from them. Thanks, guys.

      Great outfit, by the way. Very classy (and not just because of the Hober tie).

    • Here’s a third thumbs up for Hober ties. I have a number of their ties including several of the Grenadine and they are all well made and you the get the length, width and all that you want without having to settle for something pre-made. I think you will be pleased.

  9. What? The most stylish Bond, Dalton had nothing to do with this look?

    Jokes aside. I love this look, but also this kind of article. Hopefully, we get to see this as a series!
    Every time I put together this kind of outfit, I always wish I’d owned a pair of black boots. Even though it’s a formal colour, it’s something I feel needs to be in one’s wardrobe when black loafers just don’t feel right.
    Also, based on what I learned from one of your previous articles, this must qualify as a “dog robber” look!

    • I agree with you E.O. This would make as a interesting series. I am always inspired by your technique of dressing, Matt. You follow the Bond Inspiration, but you do not cosplay the character. I like the barleycorn tweed hacking jacket look you recently posted on your Instagram story. I like how you pair this jacket with the pink shirt. Great review of a great jacket.
      My regards

  10. I’ve visited this site now and then, and in the past year, quite regularly. Thanks for continuing with this blog… and an instructive and useful post! I hope you continue the blog for years to come.

    I’ve been rewatching the Mission: Impossible films, and thinking about Bond sartorial comparisons–especially the most recent M:I film or two. Perhaps a blog entry someday?

    Thanks again.

  11. The jacket is a nice one and as you suggests it the cut is classical but beyond it I’d say timeless style. That said there is a special feature much appreciated, the natural position of the upper button, the one to button; a contrast with modern production on which the upper button is situated slightly higher.
    Now I’m heading for amazon to order a copy of your book.
    Best regards from France

  12. It’s a good look on you, Matt (though I might have selected a grey a few shades darker for the tie for a bit of contrast in the ensemble, myself, but I’m biased ‘cos I’m a very fair-skinned guy and any costume in light monotones washes me out).

    Can’t help but wonder if that jacket is full-canvassed? Or only the enteral compromise of ‘half-canvassed half-fused’, for which we can thank the Germans (well, it did lower suit prices dramatically, plus there’s much to be said for the ability to wear a suit on a day out and not having to worry too greatly about spills or mud or pigeons . . .)

    • It’s indeed a full-canvas jacket.

      If you have fair skin and dark hair, a darker tie would indeed look better on you. But if you have light hair or no hair, you would look more washed out with more contrast. It helps to match the contrast in your outfit to the contrast in your complexion.

  13. Looking back at this post, I must say I really admire the checked jacket you own Matt and you assembled the outfit beautifully! Being a young man (approaching his 20s), I would very much want to have a tailor make me a similar looking jacket as it would fit many of my day to day needs (where a suit maybe too formal and a sport coat would be better). Though being a short man at only around 5’4 1/2 (and fairly lean), would you say Matt that the pattern of your jacket would be too big and unflattering to a man of my stature or is it something not too big that I can pull off and would still flatter me well?


Please enter your comment!
Please enter your name here

This site uses Akismet to reduce spam. Learn how your comment data is processed.