Two Very Different Jackets and Jeans


When a jacket-and-jeans combination works well, it is one of the most stylish outfits a man can wear, successfully bridging the casual and the formal, and merging the best elements of both.

It is, however, hard to get right. As mentioned in a previous post on The Newsreader Look, if the jacket and other elements in the top of the outfit are too formal, you can split yourself in half – giving the impression that you only paid attention to your upper torso, because you are going to sit behind a desk on TV.

The key to getting that combination right is making sure the fabrics of the more formal elements – jacket, tie, shirt, possibly handkerchief – are as casual as they can be. So no suit jackets (worsted wool cannot look anything but smart), no silk ties, probably no linen handkerchief and realistically no white shirt.

Two recent photos from the Sartorialist illustrate this very well. The younger gentleman has chosen casual fabrics for everything in his top half: rough woollen jacket; silk, stuffed handkerchief; a wool or cotton-mix tie; and a blue, oxford-weave, button-down shirt. By getting the fabrics right, he has managed to wear both a tie and handkerchief with faded jeans and plimsolls; the ultra-formal with the ultra-casual.

This is one extreme end of the spectrum: every fabric here is the casual choice. He could have opted for one or two more formal fabrics (white shirt, cashmere blazer) and it would still have worked, held in place by the casual material of the shirt and tie. He didn’t have to play it that safe.

The second, slightly older gentleman is at the other end of the spectrum. The shirt is white, of a smooth cotton with a spread collar. It is accompanied by a white, linen handkerchief. The material of the tie is hard to discern, but it is certainly more formal than that of the previous example. The only saving grace is the herringbone jacket.

Now, the jeans are admittedly darker and smarter. So the top half has less work to do in meeting the bottom half half-way, as it were. But the top half is still too pristine. The way the handkerchief is folded so precisely. The flash of a tie clip. It all smacks of dress attire and isn’t suited to jeans.

He wouldn’t have to change much to get my (entirely subjective and arbitrary) approval. Just wear a blue shirt. Or stuff the handkerchief in. Even unbuttoning the shirt collar would save the day.

Jeans and a jacket can easily go wrong. But bear the materials in mind and you’re half way there.


Simon Crompton is a journalist and a style enthusiast living in London, who blogs at He has too many suits.


  1. Great observations on the proper way to mix jeans and a jacket. I loved those pictures from the sartorialist also, he has alot of great photos on his page.

  2. Nicola Linza says:

    I will preface this by stating that I respect your opinion nine times out of ten Simon, but this time I have to disagree with you. I find the man on the right looking positively polished, and very urbane. He is clean, crisp, has a great looking leather bag, well-styled hair, and good glasses. This man can take his casual outfit many places in one day from lunch to shopping (and not being looking at with a skeptical eye by the staff) straight on to a casual night out. Whereas, the boy on the left, while there appears to be an honest attempt to achieve a pulled together look it is however one that is all wrong in my view. Let us examine this in detail; the boy’s outfit shows a lack of quality in fit and fabrication. He is wearing elements that look to me as if they belonged to someone else, or are from a flea market. It is pulled together but not in my sense of the phrase, only by the fact that each piece is obviously distressed, and not in a good way but from age, washing, and too much wear. The jacket is rumpled, the tie looks faded (and is nearly in his crotch,) the right pocket flap is missing (or tucked in,) the jeans are short and have holes (that do not appear to be designer styling but obviously from age and wear,) the footwear looks juvenile, and the bag is too big and ugly. Frankly, at first glance, with that bag, my initial take was that he looked positively disheveled. There is nothing contrasting as there is nothing ultra-formal about anything the boy has one in that photo. I thought you were contrasting the two, but to see that you find fault with the man on the right amazes me entirely. That man on the right could take that look from morning to night. I applaud the boy for the honest attempt you have shown, but he would find himself thrown out of a few establishments with that outfit, of that I am sure.

  3. I completely agree Nicola. The man on the right looks sharp and impeccable. The young man on the left looks ragged. As if he read this blog in the future on jacket and jeans and tried to attempt the look. Yet he bought all his clothes (jacket,jeans,shoes) from a thrift shop. The only thing wrong with thrifting is when you purchase items that look like they belong in a thrift shop.

  4. i agree with nicola also. i believe both of these were taken at the ralph lauren show by scott schuman during fasion week. both looks are very good but very different. yet, both looks fit the wearer. well- cut, premium denim these days looks as formal- and cost about as much as a great pair of slacks. i know here in dc i wear tailored blazers with high quality shirts(robert talbott, rl purple label, paul smith) and matching quality ties. in the winter i am a tweed and flannel whore. i love this look because i can go right from work to a great happy hour and get told how great it looks from the subway to the club.

  5. by the way, here’s alan flusser doing it impeccably.

  6. Nicola Linza says:

    I had not seen that interview with Alan Flusser before, that link is very good, thanks Derrick.

  7. Nicola Linza says:

    I am glad to see that I was not alone here. Look, many of us have great items that we have inherited, that we take on as our own, and use with great success. I think I am safe to say that applies to vintage finds too. So yes, secondhand is perfectly fine in my view, as long as it does not look it – that is the key, as “smooth” stated (that was an excellent example in your comment “smooth,” regarding the issue of thrift.)

  8. Our problem with the guy on the right is perceptional; from the pic he looks sharp, but we’re not seeing the jeans as jeans….just as dark slacks or khakis which would have been the correct choice based on the rest of his ensemble.

    I suspect if we saw the entire outfit there would be a complete disconnnect between the top-half and the bottom.

  9. once we hit the era of $200+ jeans, i’m sure we all can agree that jeans are looked at differently in functionality as well as aesthetic. the diffence between what you would wear a pair of classic-cut, raw APC jeans for vs a pair of worked over diesels is stark. there’s no longer a monolithic way of looking at jeans anymore. in both of these pictures, the jeans represent what the wearer was trying to put across and personally i believe the gentleman on the right did it much better.

  10. Nicola Linza says:

    You bring up a valid point, for the man on the right, if they were simply dark slacks or khakis…yes, perfect; however, I have no problem here as denim, as we have to consider that the upper leg of the man on the right is dark blue, and fitted, as a jean would fit. Therefore, we have to presume they are certainly dark denim, simply dark crisp denim that I have to say works perfectly with the crisp upper half. I just would not pair that upper look with worn denim, ever. Well, frankly I would not wear worn denim in the city anyway, no matter the circumstances. I wear that type of look on the right many times and with dark denim. I would have liked to see his footwear choice, with that particular look and tote. I would specifically pay attention to the footwear, to balance the upper half; as footwear always tells more about a man than most else. What I would have done here on the right is say Gaziano & Girling’s Canterbury in Vintage Cedar that is precisely my gut choice, something clean and chic, a tad darker than the bag, with just a hint of detail keeping the overall impact minimal. The mid-section pant region is dark so regardless of fabrication, it simply blends between the upper half and the footwear. Any well cut dark pant would work on that man, of course, the tote, I also believe cannot and should not compete with the footwear and the most tailored item, here being the blazer. The look on the right just works me. It says simple, unadorned, and clean, timeless. To me, one cannot go wrong with that particular look; crisp, minimal and clean, it is always a powerful, handsome casual look for a man, of any age.

  11. Simon Crompton says:

    Thank you all for your comments and I have to say I agree with nearly all of them. To me the chap on the right is just too perfect – I think it’s those damned points on the pocket square.


  12. Nicola Linza says:

    It is honestly good to hear from you. Please allow me to make clear that I find your fashion sense to be important, and your sense of color, in my personal view, is exceptional (I never say such things lightly.) I also find it important that you consistently chose to write especially on issues of men’s style and tailoring that many tend to overlook. We have all been able to re-examine our individual position on this particular type of look from your presentation, and such a push and pull process is never easy, yet it is the foundation for a great style forum. This article has certainly created such a debate; this has been one of the liveliest discussions I can remember on an issue. I would like to think we all learned something in the process. I have to say that I appreciate the serious and open element of Mensflair. This site is one that allows for an open and honest exchange of various positions on men’s style. Here one consistently finds high levels of talent, honesty, sincerity and authenticity – that is important as many are coming here from different parts of the planet and are from different backgrounds. I believe a man’s individual personal style is not a copy, or one hit wonder taken from another, but is one developed over a lifetime. I personally do not believe personal style is developed by simply looking at or taking pictures of strangers on a street corner, but by personal trial and error after careful consideration of the quality level of what one is being presented. It takes frank open discussions where knowledge is critical, depth is essential, and honesty is genuine. Mensflair allows for that rare interjection of wide-ranging fresh and maybe overlooked approaches and ideas to men’s style; and frankly, to use an overused expression – at the end of the day, that type of interchange is where many great original ideas can be formed. Thanks Simon, you gave us something here to consider, examine, and re-examine.

  13. Neil Chappell says:

    Personally I cannot stand the jacket & jeans combination. And tut to myself when I see it.
    The only time I have ever seen it work is on Daniel Craig in Layer Cake, however Daniel Craig can look good in anything. Mere mortals should steer well clear!

  14. layer cake is awesome! to each his own. i live in the jacket/jeans combo. jeans can take the hustle and bustle of city life much better than any pair of slacks i’ve had. plus they wear out cool:). by the way nicola, those g&g shoes you mentioned are tres cool. what other shoe brands do you dig?

  15. Nicola Linza says:

    The top item on the page link below is the black monk strap I was mentioning at Artioli, actually I like all three selections presented on that page,