Become More Stylish As You Get Older

It is your mission in life to become stylish, the older you get.

This is an article about being stylish as you get older. It is based on the time I lived in Japan and in some ways is related to an earlier article I wrote on Charisma.

When you’re living in a new country, you become as a child again. Everything is new and lots of things record themselves onto your mind. Its been almost 6 years since I left, but its funny how when I think of blog ideas, stuff from Japan keeps coming back. They’ve been there floating around in my grey matter for years just waiting for the chance to be released.

A Country of Stylish People

This is not Paris or Milan, but it could be. If you’ve been to Japan and especially Tokyo, you’ll notice that many people look good.  It’s not just the young people who care about fashion, but also the middle-aged. Disregard the salaryman and salarywoman (Office Lady) look. This is simply a work uniform.

Japan is a strongly consumerist society with plenty of department stores and brands. Perhaps it’s no different to the West in this respect. However in Japan, I would say that a lot more people have a good sense of aesthetics.

They know how to pick clothes and look stylish. They design their style. It’s not just about expensive brands for them. It’s about everyday brands that make them look good. If you took a hip Japanese person dressed modestly in well-thought-out clothes from Uniqlo or Muji, and put them next to a young rich Chinese tourist carrying Gucci and wearing Prada, the Japanese person would probably look much more stylish, even though the amount of money they spent on clothes is far less.

Being stylish is not necessarily about spending huge amounts of money, though that helps, but having an eye for style and fashion. This combined with them being some of the most slimmest people on the plant, sure does make them all look good.

Not Seeing the ‘Stylish’ Light

Before I went to Japan, my fashion sense was next to non-existent. There must be many old pictures in people’s photo collections of me looking like a fashion-casualty. I didn’t wear the right sized clothes. I sometimes bought the most uncoolest, cheap tops from market-stores and wore them without any sense of the awfulness I was projecting onto the world.

As a school kid, I bought a Harley Davidson belt buckle and I may even have worn it once. By the way, I grew up close to Birmingham, UK, not Birmingham, Alabama. This is not biker or cowboy country. I bought clothes from questionable shops. You know something is wrong when the shopkeeper tells you they’ve run out of shopping bags so they have to give you your clothing in a black bin-bag.  I’d tuck my shirts into my trousers (as a young man). On one occasion I even buttoned my shirt all the way to the top with no tie – a terrible fashion faux pas and I probably dressed worse than your dad. And I was in my 20s. Please, why did no one put me out of my misery?

Some Redemption: Learning to Become more Stylish

However after living a short time in Japan, their sense of fashion and style rubbed off  on me and several things happened. I bought my first ever Men’s fashion magazine when I was there and I also willingly started going to a local department store to check out what they had. I also started observing other men to see how they dressed and then started experimenting with my own fashion. After time, I even started getting some compliments on some of my choices of clothes and footwear, and if you receive compliments from Japanese men, then you know you are on the right track.

If you want some unique fashion advice, I recommend checking out the Admiral trainers brand in Japan. Surprisingly, it’s actually a British brand, but it’s completely unavailable in England. Its only sold in Japan and its looks similar to Adidas. Also watch the Japanese clothes sizes. They’re usually a size smaller than their Western counterpart. A size M Japanese item is the equivalent of a size S in the UK, even if it is the same brand. You need to try on clothes there.

Some Examples from Japan

Going back to the title of this post. I saw some of the most incredibly stylish elderly people in Tokyo. One time I was waiting in a clothes shops and an elderly small man walked past wearing a black suit and black shirt. He was well-groomed and carried off a Sean Connery look with his balding head and grey hairs. He looked great and quite sophisticated. Although, I wasn’t sure if he was a shop worker at first. Either way, he was stylish. I saw several elderly Japanese women, dressed splendidly walking around. Often in black. Their choice of clothes, jewellery and their look was well thought out. They were absolutely stunning and after seeing these people, I thought, when I get old, I want to be like them.

Seeing them made me appreciate fashion even more. It really is important. It is a form of self-expression. We are given these shells to experience the world with. Well what’s wrong with painting them the best we can? If we can find pleasure in expressing creativity on paper or on blocks of wood or clay, well why not on ourselves? Fashion and style are some of the things that give our reality colour. It is something to be enjoyed, but also it can be unique, a way to express our distinct style and taste.

Ageing does not equal becoming less stylish

Perhaps we have this negative perception towards ageing. That old people look old, they dress old, they talk old. Because that’s what old people do. But its not true. When we get older, we can become stylish. Even more stylish than when we were younger, because we no longer have to try as hard as when we were younger. We can dress to impress ourselves, not our peers. No one expects an older person to look stylish so you’ve got nothing to prove.

If fashion is not interesting to you, than that’s fine. My father doesn’t care for fashion and will wear second-hand clothes or hand-me-downs gladly. Basically, he is real ‘old-school’ guy. He was born at the start of the war period and grew up in incredible poverty in London. It coloured his mindset accordingly. I do understand his views, but it did make me a little depressed to see him wear a 20-year-old t-shirt that was literally falling to pieces. I would describe it as a T-rag. It was that bad. It wouldn’t have been any big deal to have thrown it out and updated it. But he didn’t want to. He was comfortable with it. He has other clothes that he proudly tells me are even older than me. Unfortunately, We’re not talking the classic vintage look. These clothes really do look their age and are long due a cremation.

Scarcity Mindset

This view towards clothes reflects his mindset. He still lives with a scarcity mindset. To be fair, it has helped him live a long life devoid of all the corrupting materialistic temptations that have been unleashed on the West since the 1980’s. However I think this takes it too far. One time, a friend of his bought him a brand new jacket. It wasn’t a cheap one either and there was an immediate transformation. It made him look really good. But typical of my father, he tried to pass it on – to give it to me. He just has an internal issue with wearing good things. But I absolutely refused to take it. That is yours Goddamit. Just look good already! Perhaps some people are afraid of looking good, afraid of standing out, being noticed?

Your Style can Reflect your Values and Mindset

I think that fashion – the clothes that you choose reflect you in a far more fundamental way than most people think. It reveals your attitudes and character. A good example is guys wearing football tops with other guys names on it. What does that say about you? For me, it tells me that you want to become part of a tribe. That you are a follower, but also that you have no sense of your own identity. Does that sound harsh? The hipsters these days are interesting. They clearly do care about style and fashion. It’s not my style personally especially the beard, but I respect that.

But again, fashion is not just the domain of the young. As we get older, it is the one area we can truly shine and it is so easy to look stylish as we get older. It is the time in life when the classic look fits. In fact its our duty to look good.

Some Advice

So here’s some general pointers from what I’ve learnt (for all ages):

  • Observe what people wear. If you see someone stand out with ‘style’ – study that.
  • Find your style. Consider it. Think about it. Dont just copy. Ask what is your style. How do you express it?
  • Avoid buying clothes in the larger mass-produced chain stores or supermarkets. Edge towards quality.
  • Don’t buy too much. A few items of good quality clothes is better, even if they are a bit pricey, will last you years longer than lots of cheap stuff.
  • You need a top quality coat and good quality shoes. And a good watch. Everything else can come from less expensive places.
  • Treat your clothes with respect. Dry-clean good quality items and always hang them up or store with care. Also polish your shoes regularly.
  • Wear clothes that fit you properly.
  • Be wary of yoga pants (for women). They’re like a double-edged sword. Some people pull them off really well. But for others, not so.
  • Never wear yoga pants (for men).
  • Don’t get obsessed with clothes. They’re just clothes in the end.


And if people give you compliments on what you’re wearing and your style, you’re doing something right. I think another consideration of how you dress also relates to your environment and the area you live. Sometime back I lived in a rural part of the West of England, and I found that people tended not to care about their appearance so much compared to the cities. Dressing too smart didn’t fit and so I started dressing down. For some this would be a positive point, but for me, this was a negative point and it made me aware that I didn’t really fit the place. It’s also not always easy to put the time into your appearance around other obligations and life commitments, so at the very least it’s worth building a default level of style. This way, you always have a minimal standard which doesn’t require too much work.

To end, its kind of ironic that I’m giving fashion advice. I’m not the most fashion conscious person around. I can be quite lazy at times with my appearance, but, I think I’ve come some way and some of my points are valid.

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