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.

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Arctic Penguin

The way the man on the right has folded the pocket square really is too much.. though even with a smart suit, such peaked folds to me just smack of some sort of hideous perfection. But I agree that the upper half does not wear well with jeans at all, even if they are dark and more formally cut/styled. Actually one of the best shots of anyone wearing jeans with a suit was recently done by GQ, of all magazines.. the shoot featured Jason Stratham wearing dark, trim but not slim dark jeans with a suit jacket and an oxford shirt, and the result was particularly inspiring in that the entire outfit worked well, and did not divide the person wearing it in the way that this week’s right hand man is divided.

I guess I’m alone in thinking that with the exception of the tie length, the young man on the left looks quite good. I feel the point of combining jeans with a jacket is to look more casual, to dress up jeans.. the man on the right simply should forgo the jeans and use some other pair of trousers.

Arctic Penguin

One last thing, something that I feel is very telling about the way someone is dressed: do they look comfortable? The young man on the left looks like he was born in those clothes. I feel that the man on the right looks stiff in his posture, and in his face, the way his arms are positioned. It’s easy to over analyze these things, but I see them nonetheless.

Easy and Elegant Life

It smacks of dress attire because (I’m afraid to tell you) it probably is… .

Scott Fazzini

Does anybody know where the beautiful guy on the right got that PERFECT bag?

Horatio

This discussion is fascinating. Personally, I find denim unacceptable with neckties or sports coats, tatty denim even more so. Yet you and your commenters discuss this at length, and I found the discussion valuable.

I agree with Nicola: to me, the young man on the left looks slovenly, and the one on the right looks sharp (though I probably wouldn’t like his pants if I could see them well). Then again, I favor a tidy appearance, and I like neatly folded points sticking up out of my breast pocket.

More generally, I can’t stand the asymmetry of the four-in-hand knot, yet I know some people favor it for precisely that reason–it looks less planned. I understand the dégagé argument in favor of spending 20-30 minutes planning your clothes so that you look like you gave no thought to your attire; I just don’t agree with it completely. I find some of the tricks employed by those who follow that school of thought to be artifice-ful (as it were)–like Gianni Agnelli’s watch–yet also acknowledge their overall superb taste.

Ultimately, it’s a matter of where the individual places the boundaries, and what, for him, bends the rules in one case, and breaks them in another.

Balfour

Dear Simon,

I couldn’t find anything in the archives on this. Do you have any recommendations as to where to find a simple cotton summer jacket? Nothing at Orvis or Barbour was particularly inspiring. Sunspel only has a Harrington jacket.

-B.

nicholas clark

I will attending my sons wedding in Thailand on the 24th January 2016 moi is a little overweight!! waist 40in, and neck 17.5 collar size, what would be the best attire for a beech wedding??? I am looking at having some white linen shirts made to measure would you suggest anything else??

Prince Florizel of Bohemia

Do you concider linen handkerchief to be more formal than linen one?

Prince Florizel of Bohemia

My apologies! I meant to write ”Do you concider linen handkerchief to be more formal than a silk one?“

Prince Florizel of Bohemia

Thank you! I understand. Off course that color, pattern and texture plays a role but I always thought that a plain or relatively simple shiny silk handkerchief is more formal than more linen, which is by nature slitghly iregular in texture.