Dear Simon,

In a recent post (The modern man needs a good blazer) you explained  how versatile a blazer or odd jacket can be, and how to wear one. The image, however, showed a jacket with a shirt and tie, and jeans. Do you think this works well? Or is a tie too formal with jeans? I like the look but don’t know whether I could ‘pull it off’ as they say.


Hi Jeremy,

It absolutely can work, but it is one of the hardest things for a man to get his head around because there are so many moving pieces. The contrast with a navy suit and black shoes is pretty stark.

The keys are colour and texture. More subdued colours and rougher textures are more casual. Match these to the casualness of the jacket, trousers and shoes.

As jeans are pretty much the most casual trousers you can wear with a shirt and tie, both should be as casual as possible. A blue shirt is more casual than a white shirt. A wool tie is more casual than a silk tie. A knitted tie is more casual than a printed tie. An oxford-weave shirt is usually more casual than a smooth twill.

That extends to design elements as well. Single cuffs are more casual than double cuffs; plackets are more casual than plain fronts; button-downs are more casual than spread collars.

Hopefully you get the idea by now.

The image from Brunello Cucinelli that you refer to (reproduced below) includes a white shirt with a spread collar and single cuffs, and a woven, cashmere grey tie. Personally I would have gone with a button-down shirt rather than a spread collar, or a blue shirt, but you can see how casual elements have been included to make the shirt/tie fit better with the jeans and brown jacket.

The image at top, taken from The Armoury’s wonderful Tumblr account, also uses a white shirt but you can see how the knitted silk tie adds a casual element. Suede in the belt helps too – more texture.

Good luck with your combinations.


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no simon, never wear a tie with a button-down shirt…


Thanks Simon, most helpful. I look forward to trying this out.


jeans should be as dark as possible, preferably indigo, and slim. APC and Uniqlo selvedge jeans both work.


Ah, one thing has just occurred: I’m a smidge over six foot, and knitted ties seem to be made for much shorter men; they all seem to end above my belly button. The only way to avoid this would be to tie it so that the flattened area which is supposed to go around the neck is actually part of the knot. Is it acceptable to have a knitted tie very short, or is there anyone who makes them in longer sizes?

Alexander Hugh Jarce

Excellent post Simon, Italian ties seem to be cut longer,maybe for more intricate knots.Either way just adjust the back blade’s length and all is well.Ties and Jeans work if the jeans are darker, as mentioned above,and not distressed.Broken in good, worn through bad and sad.


Simon– Your suggestions have made the tie/jeans combo as palatable as possible.
However nothing will ever make me like it.

Theodore Bouloukos

Shocking to me that this combo still leaves some befuddled. I can go back 30 years to prep school (American equivalent of your public schools), and recall younger faculty sporting such a look without note. By the way, Simon, you looked great in your cycling togs. Thanks for your blog!


I strongly disagree that plackets are more casual than plain fronts. At the very extreme, yes, a bib-fronted evening shirt for wear with white tie will have a plain front. But in every other formal context from black tie down (the abomination of pleated and fly fronts aside), it’s plackets all the way. By contrast, when I want my shirtmaker to run up a casual short-sleeved number for the seaside, I’ll tell him to give it a flat front.

Roman Kaiser

I don’t like the jeans-and-tie look at all. Partially because I think trousers should always have a crease. But the look either says “I have to be formal by wearing a tie but I want to be comfortable wearing a jeans.” or it says “I am young and fashionable. I am wearing a jeans and a tie as fashion accessory.”


I ike this look a lot but probably wear with a tie loosened around nthe neck and deliberately left a little undone .. makes it look more relaxed, and although not strictly correct gives a little sprezz to the look..

One issue I have with this though is can you wear any type of coat over this? With a suit it is natural to put on an overcoat ( perhaps a camel one like the one you had made at gb or a mac in more temperate but rainy weather), with a blazer or sportscoat can you


Cont… With a blazer or sportscoat I not sure a mac or overcoat would work although may be equally necessary? How would you play this Simon?



Hello Simon. I have this tie in mind from Drake’s to wear with my PS Oxford Shirt and denim jeans. Let me know your thoughts?


Hello Simon. Considering the fact that I intend to wear jeans for now and as I’m building a casual wardrobe around it and the pieces that would work with and around jeans. My thoughts are of having two indigo raw and around two mid-blue colour jeans and rotate them? Let me know your thoughts?