Re-using the Denim Jacket



I am often surprised by the number of friends and acquaintances of mine who admit to owning, though rarely using, a jacket constructed of denim. I am a monumental hypocrite in this regard, as I still own one bought earlier in my youth; one which I enjoyed wearing with smart black trousers, a white shirt, a slim black tie and black loafers.

Though not an offensive aesthetic in retrospect, it is fair to say that I have moved on – in both age and style – since those days and, though I cherish the fond memories of wearing the jacket as well as wrapping it around the shoulders of ludicrously underdressed young ladies on a stumble home, I have not found many uses for it recently.

This is not without trying, as I have often attempted to mix it into an ensemble for an evening’s fun on the town. The trouble is, I look at the jacket and see myself eight or nine years ago; a cocky, floppy-haired whippet. As I scan up to my aging face, conservative hairstyle and tired eyes, it becomes clear that I need to rethink my continual efforts to reincorporate it into my regular wardrobe. Call it age denial, call it sentimentality, but I cannot find the courage to bin the thing. Instead of being anti the denim jacket aesthetic, I have come to the conclusion that I simply don’t understand it anymore.

However, on pondering its removal to make some much needed space in my reserve wardrobe, I thought through some potential ensembles which, come the spring, may be worth attempting. It is often worn with matching jeans, which is a disastrously studied and dated look, though there are some who wear it with denim of a contrasting tone and texture; a stonewashed jacket with new denim, and vice versa. However, I think it is best deployed when no other denim is on show, particularly with khaki chinos; it needs to stand out, and therefore needs contrasting materials and colours.

This is perhaps why, in my mind, a suitable spring ensemble for a denim jacket might be a pair of slim fitting khakis, a white shirt, a denim jacket and a pair of sockless penny loafers. Arguably, still a youthful look but one which a man nearing thirty has more confidence in attempting. Adventurous chaps may wish to add a seersucker bow tie to prep it up and, for the Layerists, to button up a slim-fitting denim jacket under a cream trench; keeping it Americana-but-still-Ivy-League will prevent it going the way of the cowboy hat.


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at


  1. wheres the prob, can’t wear a denim jacket then don’t

  2. With respect, you’re overthinking this one. I’m 34 and wear a denim jacket whenever the temperature and formality are aligned. You’re right about chinos being the solution. Beyond that, rock it out and relax. It’s a relaxed look, but the shape it provides keeps you from looking like a slob. It might be one of the easiest damn things I own.

    Some rules off the top of my head:
    1. Avoid the “Denim tuxedo”
    2. Wear it with pride.
    3. Don’t be afraid to use it as an ice-breaker.

  3. Hmmm…
    I do have one. Lee Cooper. Somewhere. Probably somewhere in my parents house.
    Bought large about age 11, I still wore it to about age 15 or 16.
    Perhaps one of my daughters might like it in ten more years.