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.

For the man who usually wears tailoring, the key is to treat jeans as a direct substitute for chinos. A straight fit is vital: neither too skinny (unsuitable), nor too baggy (hello, dad jeans). The denim should be dark and uniform in colour with no distressing. This straight-leg pair are from Richard James so they feel appropriately grown-up and properly tailored. Ideally, the jeans will finish on the shoe without the need for an attention-drawing turn-up. Opt for a softer shoe than the usual black Oxford – blue jeans and black shoes rarely go together. Chocolate-brown suede chukka boots are understated and will combine well with a dark-brown leather belt without being too forced a match. Similarly, a formal business shirt with a spread collar and double cuffs will jar with denim – a cotton button-down is more versatile and can be worn with or without a tie.

Double denim is not easy to pull off successfully. Those who manage it tend to be confident, creative types. A suit would stifle their artistic flow.

A useful tip to make this look suitable for work is to incorporate colour, pattern and accessories to break up the double denim – achieved here with a bright check flannel shirt, jeans that have been turned up to show a chunky brogue boot and a canvas bag. Using the denim jacket as a layering piece underneath a statement item – a brightly coloured coat – also softens the impact. This is a true workwear look beloved of urban frontiersmen who take their locavore produce, vintage vinyl, indie cinema and selvedge seriously. The indigo denim will likely be raw rather than prewashed, and the turn-up will highlight the selvedge – a telltale sign of quality as well as another pop of colour. (For non-denim nerds, selvedge – or “self edge” – refers to the woven seam running down the outer legs of good quality jeans which helps to prevent the denim from unravelling or fraying.)

It often pays to be dressed for anything in case the unexpected happens – the CEO drops in unannounced from global HQ, or you’re asked to attend a client dinner and you’ve no time to change. 

This versatile look will work whatever suddenly pops up in your iCal. Blue Blue Japan’s cotton twill will Jedi mind trick any doorman, no matter the dress code – whether it’s The Ritz (no jeans) or Soho House (no suits). Even though these are cut very slim, they are blended with stretch to ensure comfort – important if you are wearing them all night as well as all day. And they are over-dyed with indigo for an inky blue colour that, when worn with a navy blazer like this, could pass for an unstructured suit at a glance. Dial up the formality with the knitted tie; dial it down without.

A man who works hard but plays considerably harder needs an outfit that will glide seamlessly from business to pleasure. It’s not your boss you’re dressing to impress: this fashion-forward look is ideal for the worker who has one eye on the clock and the other on the intern he’s taking for a drink once it hits six.

Black jeans have rock‘n’roll connotations, but this pair from A.P.C. are not so figure-hugging as to cause any discomfort – either for the wearer or for whoever is sitting opposite him in the team meeting. Black denim looks smarter than grey and goes well with black boots. Combine with a slim-fitting white shirt worn buttoned up sans tie for an office-friendly look with just the right amount of edge. Just don’t come in wearing the same shirt the following morning.

Many offices have informal dress codes – particularly on a Friday – but casual shouldn’t equate to slovenly. You can still be well-dressed and dressed down. The lighter the wash of jeans and the more whiskering and fade lines, the more casual they are.

Ordinarily, jeans as well-worn as these ones from J.Crew would be best kept for the weekend. But paired with tan suede desert boots instead of sneakers and with a collared chambray shirt and washed-out unstructured chore jacket in place of T-shirt, so that all the faded colours work together, these jeans are elevated to office-appropriate (for a non-client-facing day). If you’re going to turn up your jeans, three is the maximum number of turns – anything more looks too bulky around the ankle. And you can always lose the sweatshirt and add the navy knitted tie you keep in your desk drawer should you need to.