In the first of a series on sartorial problem-solving, we show you how to wear denim at work.

Casual Friday has a lot to answer for. In today’s fluid and creative business environment, working and socialising often happen at the same time – or they can certainly segue from one to the other. (We’ve recently heard people using the phrase “bleisure” – a portmanteau of business and leisure. Then we cringe.) This brave new office world can present dilemmas for the modern working man. Such as: “Can I claim that dinner back on expenses?” and “What should I wear?”

We’ll leave you to wrestle with the former conundrum, but as for the latter, we would like to present the business case for denim.

Many professional men, particularly those north of 40, are most comfortable wearing a suit to work. It is a uniform of sorts, requiring little mental exertion beyond picking out the right tie. It is when they are encouraged to dress down and loosen up – whether for casual Friday or a company away day – that panic sets in. No one wants to be the stiff in the suit when everyone else is dressed more informally. But the wrong jeans – otherwise known as “dad jeans” (or, in the States, “Obama jeans”) – can quickly make someone look as dated as they would carrying a flip-phone.

For a generation that has grown up with digital fluency as its birthright and jeans-in-the-office as a default setting, the challenge lies in dressing them up enough to make them suitable for the working week. This usually means choosing dark jeans with minimal wash and no distressing.

The trouble is, most of the men you see photographed wearing denim well – rock stars, actors, off-duty sportsmen – never have to darken the doors of an office. So by way of role model inspiration we have assembled five very different denim-based looks that you can dress up or down as your diary dictates.

And good luck with those expenses.