One of the key reasons I believe well-worn clothes look better on everybody is that the wearer is inevitably more comfortable in them. You never look stylish when you are conscious of what you’re wearing.
“Clothes should be worn. They should be used. They become more personal, more distinctive and more beautiful – for me – when they have been worn lovingly for years.
This leads to several conclusions. First, invest in clothes that are good enough to last a long time. Cheap clothes come and go. You rarely develop the same connection with them as with something that has worn with you over several periods of your life.
Second, don’t acquire too much. I know it’s a wonderful position to be in, but I know I have too many shoes. Even with a rigorous policy of giving away or selling old pairs, I have too many shoes. It is noticeable that the newer pairs take a lot longer to acquire character, because they are not worn as much or polished as often. They will probably never catch up. When you get more money, buy better shoes, not more shoes.
Third, look after clothes well and pay to have them repaired. Few stains can’t come out of a shirt if dealt with quickly. They can be taken in and out (to an extent) as you lose and gain weight. Treasure the frayed collar or cuff as signs of your connection to that cloth – don’t wear that shirt to a job interview, but be aware of how good it looks with your old denim and worn-in brogues at the weekend. This is age-worn, old-money style.
At some point you will have enough clothes. That’s ok. Like gradually filling up your house with good-quality furniture, your consumption will inevitably slow. Spend the money on something else. Your kids perhaps. The consumerist urge will fade, and give way to a far richer, more rewarding period in your life filled with easy, simple elegance.”
Words of wisdom from the menswear blogger Permanent Style.