I started losing my hair in my twenties. Looking back at pictures from college, you can see the tell-tale signs of receding hairline and, less obviously, a rapidly thinning area on top (accentuated by a double crown).

I did experiment early with cutting it all off. While I was travelling in Israel, aged 20, I let a friend shave my head and sent a picture back to my parents. My mother wasn’t a fan; she thought it made me look ill. 

Perhaps it was that comment, perhaps it was having a job and being more professional, but it took me a long time to shave my head again. It’s only now, in my forties, that I have it almost as short, and would be happy cutting it back to zero. 

I mention all this because a couple of readers asked recently what I thought about hair. They were balding and unsure whether to cut it all off. I don’t know anything about pills or plugs, but I do have opinions on how a man presents himself, and have my personal experience to relate. 

My overall take would be, don’t worry about shaving your head. Everyone looks better than they think they will and it’s amazing how quickly all your friends, family and colleagues (and indeed you) get used to it. 

Plus the biggest danger is definitely on the other side: appearing a little ridiculous and unconfident by hanging on desperately to the hair that’s left. Keeping the hair long and combing it forward or, much worse, growing it long on the sides and going for the Bobby Charlton combover (above, first image).

I know a fair few people in fashion that speak favourably of the Pier-Luigi Loro Piana style of haircut, where the hair is kept long and swept back, almost revelling in what’s left (above, second image). Aside from liking the style, I think the reason is that speaks of confidence – something the combing-direction options don’t. 

I did not follow this advice. I worried about shaving my head, and only cut it shorter gradually over the years, always feeling self-conscious and afraid it wouldn’t suit me. 

I did an article a couple of years ago that I think about often – on learning to dress my body better. It included a few different examples, including height, weight and sloping shoulders. But the image that stayed with me was the one above, showing how my hair has got shorter and my beard longer over time, and how much better I look as a result. 

My hair is even shorter now. In the right-hand imageI was cutting it to grade 1, last year I shifted to 0.5. I still wince when I see my long, pale head in a photo, but I now realise that having even slightly longer hair was accentuating the effect, not hiding it. 

As with a few things in the past few years, I owe some gratitude to Ethan Newton, who in his gruff-and-loving way has pushed my hair and beard in these directions. God I hate it when he’s right. 

I also owe something to Stefan Avanzato, who has become my regular barber and I featured originally in 2020, in a parallel article about beards. 

“We have this conversation so often,” says Stefan. “Men aren’t always keen to talk about it, but when they do there’s a real outpouring – all the worry they have, how they think it’s going to affect their image.”

“I think you’re right Simon that most people look better with a shaved head than they think they will, but I also think they shouldn’t cut it off too early,” he says. 

“There are a few options with how the hair is cut – often particularly short at the sides – and with using products to plump up the hair. If you want to keep your hair it’s also important to start taking supplements earlier rather than later.”

The virtues of pills and surgical treatments are not something I’ll go into (although readers with experience, feel free to jump in) but I would say it’s invaluable having someone like Stefan (below) to talk to. He’s seen a lot of people try these things, he’s seen the results over a period of years, and he’s both more objective and personal than random coverage on TikTok.

There’s probably one parallel with clothes here, in that it takes all of us time to get used to a new look. You get a western shirt for the first time and you probably feel self-conscious about the pearly snaps, walking around just waiting for someone to say “Howdy, cowboy!”.

But five or six wears later, chances are it will feel completely normal, and when someone says “Yee-ha” as you enter a room, you’ll simply smile indulgently. Silly little frightened man. 

Cutting off your hair is the same, with the bonus that I think it’s unlikely anyone will ever actually tease you about it. There’s too much respect for it, too much recognition of the bravery it took to change your face – that most prominent part, the bit everyone looks at the most – so dramatically. 

So take Stefan’s advice and cover all the options first but, if cutting all your hair off is the best option, do not be afraid.