Tuesday, February 7, 2023

How To Dress Like A Millionaire While Staying In Your Comfort Zone

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When people win the lottery, there is usually a lot of attention that comes with it. Their local town wants to interview them. They show up on TV. If they donate any money to restore or repair anything in town, they will have pictures and attention from that. Their friends, family, and just about everyone who ever knew them will come to see them. With all the attention they get, they will want to look their best. But the idea of getting dressed up every day is not appealing for them. So, we would like to offer some tips for dressing like a lottery winner, while staying very comfortable in your new fashion. 


Just because people who wear expensive clothes look sharp does not mean they are uncomfortable. Actually, quite the opposite is true. Quality clothing is made of natural fabric that breathes keeping the body temperature at a natural level. There is a different look to the way the shirts, trousers, jackets, and jeans fit. That is because they are altered to fit the body. It is much like slipping your hand into a glove. A good fit gives you flexibility. There is no friction, binding, or pinching. Most off-the-rack clothes are too snug or too baggy. People get used to wearing loose clothes so when they see clothes that are not loose they assume they are snug.

What is casual to rich people?

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The easiest way to determine what to wear is to separate your wardrobe into two categories. As you become more experienced with fashion, you will add more categories. Right now you are going to look at dressing correctly and comfortably.

When a rich person is dressing casually, they are wearing clothing that is acceptable to wear to lunch in a 5-star restaurant for lunch. You would see the style of clothing on people who are playing on a nice golf course. 

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Rough fabrics, such as linen and canvas can take an outfit down a couple of notches, whereas leather shoes and smooth fabrics will take an outfit up some.

During the casual hours (before 8:00 PM) lighter colors are expected. 

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Men will wear:

  • Tennis (collared) shirt
  • Polo shirt
  • Button-down
  • Pants or shorts to the knee
    • Khakis
  • Well-fitting jeans in some cases
    • In places that will allow nice jeans, you can usually wear nice sneakers 
  • Leather loafers
  • Fine-polished tie-up shoes

Women will wear

  • Suits
  • Collared shirts
  • Skirts to the knee
  • Tailored dresses or dresses made by hand
  • Capris made of dress-pant material
  • Some places will accept well-fitting jeans or jean capris
  • Button-down shirts

Shoes will be leather flats, loafers, fine-polished tie-ups, and nice sneakers if jeans are allowed. Clothes that show cleavage, the back, shoulders, the stomach, and the thighs are not acceptable for daytime casual wear. Flip-flops are never okay. For that reason, sandals are often questionable. It is best to avoid them. Jewelry and perfume are to be minimalized. Clothes should be ironed and hair should be neat. Make-up should look as close to natural as possible. 

Casual elegant, after 8:00 PM

The sun has set and you are going to a nice place for dinner. It is a casual-elegant dress. Like your lunch wardrobe, there could be some slight variations depending upon the restaurant you are visiting, but this is your basic guide. 

You will now switch to dark colors. Navy, black, dark gray, and chocolate are good choices. Men will wear suits usually. At the minimum, they will wear jackets over button-downs and dress pants. Women will wear suits, dresses, or skirts and they will be expected to match or at the very least closely complement their partner’s suit. Note, you will always do well with a black or gray suit for him and a black dress for her. You can add color with the tie and pocket square. The purpose of this is to look “together” when seated. Same-sex couples are not expected to wear matching clothes but it is a good idea to wear complementary colors.  

Now is the time to wear your fine jewelry and wear more make-up and spend more time on your up-do. Leather shoes are a must but ladies can wear their heels if they would like. Do not go above a medium height. Men, if you have a flair for dressing, you can opt for a bold shirt in something like red or royal blue. But unless you are sure of your talent, stick with white or a light stripe.

As you can see, this is a very simple transition. Every outfit is comfortable and easy to wear. They are light to medium-weight and should move easily. The shoes are high-quality and they will be comfortable and last for years. You will fit in well in any situation from business meetings to formal dinners. You will do it all, like the winner you are. 

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Anshu Dev
Internet trailblazer. Travel ninja. Social media evangelist. Incurable explorer. Subtly charming organizer. Tv scholar. Alcohol geek. Certified creator.

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