For the balding man, the world of style can feel somewhat inhospitable. Models tend to be blessed with full, leonine hair, while the grooming pages – when they do address the hair loss that afflicts 40 per cent of men by age 40 – nearly always do so in terms of staunching the loss or disguising your follicular trajectory.

But why? The secret to good style is about working effectively with what you’ve got. Mr Stephen Monaghan – director of fashion PR agency Sane Communications, co-publisher of The New Order magazine and notably stylish dresser – puts it perfectly: “Being bald is not the same as going bald. Going bald is where the stifling insecurity emanates from. For me, it added something to me as an individual.” Or, as Mr Larry David once said: “Anyone can be confident with a full head of hair. But a confident bald man – there’s your diamond in the rough.” With that in mind, here’s a helpful guide to see you through it all.

When you finally go skinhead, intentionally or otherwise, you’ll need to reassess your wardrobe. Your proportions will have changed slightly so oversized jackets can swamp you. Anything military should be worn in moderation – too much camo and you risk looking like you’ve been kicked out of the TA. Crew necks should have a closely fitting collar – wider openings can make you look tortoise-like. Bomber jackets are risky as they can feel redolent of the worst end of skinhead culture; jackets with a shawl collar work better.

Generally, shaving your head will make you look a bit “harder”, so think about softening and relaxing your outfit to counterbalance this. Use colour and patterns to contrast the stern look going on up top. As Mr Monaghan points out, the benefit of a shaved head is that it makes you something of a blank canvas. It frees you up to have more fun with matching, clashing, colours and shapes. “I like pattern, I love texture and silhouettes, from iconic styles like an M65 to a technical piece, all the way to left-field sportswear – I choose to mix them.” Push the boat out.

Ms Marie Wilkinson, design director at Cutler and Gross, says that “bringing angles to a rounded shaved head would be the top of my list – square, rectangular and D shapes would look best. Translucent and pale tones work really well as subtle colours come into their own on a blank canvas.”

Mr Jason Jules, a stylist and one of London’s most well turned-out, close-cropped men says, “I tend to recommend simple, classic ones with solid or half frames.” According to him, prescription glasses that are too over-the-top tend to dominate the face. “The impression you want to convey is that your specs are a functional piece that happens to look good, rather than a fashionable piece that might be functional, too,” he concludes.

Sunglasses are a challenge. Even the mildest-mannered baldhead can suddenly look a touch disreputable once the shades go on. Ms Wilkinson avers that “an oversized rectangular shape with a luxurious and complex combination of metal and acetate,” is your best bet to avoid the thuggish look. “I am all for recommending flatter base curve lenses,” she adds. “Either flat or 2-base curve, 4-base, or at the most 6-base to avoid the wrapped-sunglasses look.”

Particularly on the paler-skinned, the regular baseball cap can make you look like you’re convalescing – the more relaxed six-panel shape from AMI and Norse Projects, or any of RRL’s Americana models work better. With woolly hats, cashmere has a tendency to cling uncomfortably to stubble, so go for regular wool or cotton.

“The beard allows for a stronger facial look and can accentuate angles and lines in the face”, says Mr Darren Fowler, artistic director at London salon Fowler35. “Any good stylist should talk you through creating lines in the beard and how they accentuate your look and how you should maintain them.”

Mr Jules makes the case for using a beard as a counterweight to your clean head. “Once I realised my hairline was actually closer to my neck than my forehead, I started allowing my beard to grow,” he recalls. “Eventually, I realised it meant there was a certain balance achieved that had been lost by going bald.” Mr Jules adds that, when developed correctly, a beard can give you the stylistic flexibility of head hair. “There are loads of reasons why I might advise a client – or another fellow bald guy for that matter – to grow their beard. It frames their face in a way that can highlight their cheekbones, gives the impression of fuller lips and actually extends their jaw line – or maybe even hides a double-chin,” he says. “Ultimately, I think beards are fun. They say, with no apology, ‘even though the hair on my head has given up on me, I haven’t given up on my looks.’”

Where possible, even a barbering job that looks this straightforward should be left to the professionals. “Always the Turkish barbers,” says Mr Monaghan. “I love the ritual and the ceremony. It makes a follicle-challenged man feel special, if only for half an hour.”

Mr Fowler stresses the pecuniary benefits of a good relationship with your barber. “Fortnightly would be the general frequency for most of our guys with a shaved head. Your hairdresser or barber will have this factored into the price list, so maybe you’re just coming in for a 15 to 30-minute appointment to maintain the look.” He generally cautions against the full wet-shave, as “the head shape would have to be super good for this. It’s good to leave some shadow as this gives a framework to the face and contrast to the skin and eyes.”

The skin up top needs caring for just as much as your face. “We need to be aware of the higher levels of UV exposure to areas that may previously have been protected by the melanin in hair,” says Dr David R Jack, an aesthetic doctor based on London’s Harley Street. “Over the long term, increased UV exposure can result in areas of increased pigmentation and other skin abnormalities such as thread veins and even skin cancers. Likewise, as hair follicles are lost, some of the natural protection from sebum is also reduced, resulting in increased dryness in certain areas. The best way to deal with these effects and protect against future damage is by using a good broad-spectrum SPF moisturiser all over the exposed scalp.”

Dr Jack continues, “Pigmentation from longer-term damage can be treated using skincare with ingredients such as vitamin C and retinol. Serums can be good, particularly those containing hyaluronic acid. In terms of dryness, usually all that’s needed is a good anti-dandruff shampoo such as T-gel.’ He further advises that skincare needs to start at the point of the haircut, not afterwards. “For those who are clean shaving, there is sometimes an issue of folliculitis. Antibacterial products can help with this, particularly post-shave preparations containing natural antibacterial ingredients such as tea tree oil.”