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Maybe you have been a working man all of your life. There is nothing wrong with that. This country was built on blue-collar workers. But now you have finally arrived! Now you have the money to live a life of luxury. You want to look the part! In this article, we are going to give you instructions for looking like you won the lottery. So, let’s get started.

Classy, not Flashy

There is a saying in high-society. “New money talks, old money whispers.” Old money has circulated through a family for generations. It is not something that you call attention to. It is understated, expected, and tasteful. A man of this status feels perfectly comfortable showing up for a casual lunch in khakis, a light-coloured polo or golf shirt, with a sweater draped over his shoulders. His clothes are not going to be bold in colours or prints. They will not support logos. They will not be made of polyester. 

His shoes will be real leather and they will be in perfect condition. Since a good pair of leather shoes last around 15 years, they should be taken in annually for any repairs and to be polished and checked over by a shoe professional. Shoestrings should be replaced and the leather should be carefully cleaned and conditioned.


Men of wealth spend money on their looks. This is not a “female” luxury. Looking good is a requirement and they can afford it. They have a good hairstylist that keeps their hair in good condition and style in a way that is easy to care for and in a way that is flattering to them. Their skin routine is important. Their skin must be clean and moisturised for a great look when they are caught by photographers. They keep their facial hair and eyebrows trimmed to perfection. 

Quality over Quantity

Many people have the idea that just because a man has a lot of money that he spends a fortune on his clothes. While he may spend more than the average man, it is because he buys clothing that is of better quality. He doesn’t necessarily buy more clothes, he buys better clothes. 

Today’s man is aware of where his clothes are made. He understands the impact that buying clothes from countries with sweatshops and no environmental controls have on the planet and the workers. A major portion of those poorly made items ends up in landfills. Many of the people who make them end up sick, hurt, and sometimes killed while working in very poor conditions. The only way to stop them is to put them out of business. 

For the lottery winner who wants to improve his style, he will first have to find a style that looks great on him. Until he has reached that point, it is best to rely on the oldest tip in the book. Stick with the classics. The classics never go out of style and will always flatter the wearer and look sharp. You can dress them up as you go. In the beginning, it will just give you quiet charm.

Here is a list of must-haves:

  • Button-down shirts
    • Several in white
    • Light blue
    • Pinstripe
  • Oxford shoes
  • Straight-fit jeans
  • 2-button, single-breasted navy, suits
  • Medium grey suit 
  • Camel coat
  • Silk tie and pocket square
    • At least two
  • Dress socks
  • Quality underwear to wear under suits
  • Quality leather belts
  • Nice watch

You can be a trend chaser or you can do what men of class have done for generations and will do for years to come. You can stay with the classics. The clothes listed above fit into that class. These clothes will never go out of style. That does not mean they have to be boring. You can easily dress them up with the accessories also listed. A nice navy jacket looks great with a neatly ironed button-down. A grey suit can go from day to evening wear with the change of light to a bold coloured tie and pocket square. 

To make your clothing look ultra-chic, take extra steps. Match the leather pattern of your belt to the leather pattern of your shoes. Buy a nice watch. The watch should be in a style that fits you. It is not about flash or bling. It should be a quality and functional watch, and it should go well with anything. 

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