The Difficult Art of Dressing Down

Had an unusual experience recently. I had an engagement in a context with which I was unfamiliar. However, I was pretty clear that it was a context in which my normal suited and booted professional dress would come across as OTT. So I needed to make alternative arrangements.

For a number of reasons I felt it was important to dress down. In part, to make others feel less uncomfortable. In part, to create a particular impression of myself. First impressions count after all…

Dress Down FridayMostly, however, it was an attempt to avoid giving the impression that I was a middle class tosser who had no idea how real people lived. I confess that I don’t think that I am a middle class tosser, but then I suspect that such people rarely do. Nonetheless, I believe that I can fairly easily give that impression when all dressed up, which is my default setting, of course.

So the task was to dress in a way which didn’t look too sharp, but neither too shabby. It needed to be conservative, so no bright colours, and sufficiently smart to look professional, whilst at the same time sufficiently casual as to project approachability without straying too far into looking like an extra on Father Ted or Rev.


I hope this sounds suitably complicated, because it was. I found that I really didn’t have anything that easily fit into that kind of category. I’ve got clothes that broadly can be described as smart, smart casual, or shabby. What I don’t have is clothing which fits into an ‘I’m not trying very hard chic.’

Moreover, there are no clear rules for what constitutes dressing down, particularly if you wanting to preserve an impression of professionalism whilst doing so.  There are pretty clear rules for men who are dressing up and the more formal you get the more clear and explicit the rules become.  However, the converse is equally true. The more casual, the fewer the rules.


I can remember reading somewhere that the art of dressing like a gentleman is to to take your time when getting dressed and then to forget about it completely. The object is to look as though you haven’t tried very hard.

When I get dressed however, I do take my time when getting dressed but unfortunately I then look like I took my time whilst getting dressed. So rather than looking like a gentleman I fear I look more like a dandy than I do Mad Men.

Mad Men

It was the dandy look that I was trying hard to avoid. I think I got there in the end but it took quite a bit of effort and trial and error.

Sometimes I fear that dressing down can be a more difficult discipline than dressing up. It can be really easy to get it very,very wrong….

Dress Down day short shorts

Anybody else have that problem?


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