The Dress-Down Friday

Credit: Pete Souza

It is said there are two types of men; those who look forward to dress-down-Friday, and those who dread dress-down-Friday. The former encapsulates all the slovenly, tie-off-as-soon-as-I-leave-the-office, ‘Beer is Life’, ‘cool clothes’ loving office-misfits – the man who should be a surfer but ended up as an account manager. He doesn’t want to be in an office and, barring his efficiency, the office rarely welcomes his apathy. However, his one moment of defiant victory comes every dress-down Friday when he is permitted to wear his beloved jeans.

Yet, whilst appropriate for the colder times of year, there can’t be anything less comfortable than wearing heavy jeans in summer heat. A recent dress down Friday at work prompted thought on the topic as I gazed upon the mass of smokers stood outside in the sunshine, predictably attired in denim. Though they may have chuckled at my green trousers and tie – “It’s dress down mate, not dress up!” – their almost religious attachment to denim and its connection with dressing down provoked a similar response from me.

As ‘cool’ and ‘trendy’ as denim may appear to be, I think it is extraordinarily overused. I enjoy wearing it but it’s remarkable that a great many men, given half the chance to break out of ‘uniform’, never opt for anything else; no cords, no linen, no moleskin, nada. Just jeans, jeans, jeans. Followers of this mantra usually take one of two lines; “jeans are ‘cooler’ than anything else” or “jeans are more comfortable than anything else.”

‘Denim jeans are more comfortable’

Bilge. Denim jeans are not at all comfortable. Not compared to flannel trousers, cords, moleskin trousers, linen trousers, chinos and almost any other trousers you care to mention. Psychologically they are perceived to be more comfortable than anything else because they are common and casual; a man can wear them without worrying someone will point and stare and without any preconceived perceptions of them being special. For the winter, cords are warmer and softer; in the summer cotton chinos are cooler and more comfortable too.

‘Denim jeans are cooler’

Maybe once, about 50-60 years ago, when jeans were a symbol of rebellion. Not now. They represent conformity, the crowd; anyone believing they are still a badge of anti-establishment youth needs their head seeing to. Instead of aspiring to attire that chases end-of-the-rainbow nebulosity, a man should step apart and choose something really rebellious (green chinos anyone?) if his desire is to rebel; if it isn’t, and I suspect this is the case, plenty of other options – khaki chinos are an excellent example – reflect conformity as ably as denim.


  1. Justin Ennis said:

    Winston! I’m so with you on this! I used to be one of those who happily changed into my jeans on a casual Friday and I gave one of my dear friends at work a hard time about wearing slacks. Then he looked at me and said, “But my pants are more comfortable than your jeans.” And you know what, he was right.

    Plus I just feel better about myself when I’m dressed right.

    Oh, and the picture of guys who wore jeans to meet with President Obama is absolutely perfect for this post, but I cringe when I see it.

    April 15, 2011
  2. At last someone has said it and most eloquently too; I refer to Winston Chesterfield’s article on dress down day at the office. I’ll just add another thought; most men wear denim constantly because they are too damn lazy to choose anything else.

    April 15, 2011
  3. Boon Goh said:

    Eloquently put! Your article addresses both style and practicality. I’ve been asked time and again why I seem to favor cords or heavy twill in the winter, and khaki chino in the summer. This article will be sent to friends and colleagues who’re still puzzled by my jeans-less life (and how I’ve managed to survive America without denim)!

    April 15, 2011
  4. Lark said:

    Never denim. I believe I have a pair somewhere for casual hikes over rough country in cold weather, but even my painting pants are actual pants. Denim stretches and bags if it’s all cotton but doesn’t hold up well if it’s not. It’s heavy in summer and insufficient in winter. It “goes with everything” and thus nothing.

    I don’t particularly mind it if it’s part of a definite look – young men in baggy pants and so on are doing something intentional and stylish on its own terms – but as a default, it’s depressing.

    April 15, 2011
  5. dennis said:

    I have been wearing jeans for many a year, and then started working in an office. I wear shirt and tie most day and I wore a suit for formal friday.

    I do wear jeans and even Cowboy boots. I still do some work that gets me dirty, I train Soilders and while i still wear a botton down short or polo will doing it, jean do take to the woods a little better thnan chinos.

    I had never wore a par of cords untill two months ago, and I was missing out. love ‘m.

    April 15, 2011
  6. dennis said:

    WoW, with all the errors in my comment, you can see why they still send me outside to get dirty….

    April 15, 2011
  7. Nice post, couldn’t agree more. Jeans definitely have a large place in my wardrobe, but they should have no place at the office. Particularly the type of jeans most men tend to wear, which add ten pounds and ten years.

    April 15, 2011
  8. Eli said:

    I partially agree. First, if your photo above was shot in the Oval office then shame on those three knuckleheads for being so boorishly underdressed…they are obviously too immature to comprehend the space in which they stand. As for Denim, yes it is no longer the “anti-establishment” symbol and conversely has become quite the uniform BUT I really love wearing my clean dark 514’s with one of my navy blue or charcoal sport jackets, a pale blue button down oxford, skinny mod tie and monskstrap shoes…now that’s “dressing” down.

    April 16, 2011
  9. Jim said:

    I never wear denim because my lifestyle does not extend to ranching.

    I don’t think most people wear denim because they are lazy; they wear denim because they are not confident enough to break with social norms.

    April 16, 2011
  10. Harry said:

    Hear hear!

    April 18, 2011
  11. VanZ said:

    As for Fridays, I work at a studio where sweatpants are pretty normal, and jeans/t-shirt is almost uniform. Casual Friday would either be pointless, or result in nudity, so I’ve pushed us in to having “Formal Friday”. People have a bit of fun, put on clothes they wouldn’t otherwise, try new things, and are set for a Friday night out looking swanky!

    Denim is merely lazy, or for farm worker? I think that’s crap. A good pair of dark indigo jeans are a solid base for a great many occasions and styles.

    And really, there’s no need to disparage something merely because it isn’t to your taste.

    May 20, 2011

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