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Step 1
The pants are the most important aspect when it comes to dressing casual. They can instantly change your attire to sloppy or professional. Look at the pants and ask yourself if you would work out and exercise in them. Chances are you would never go for a jog in a pair of jeans or khakis, which means these are perfect pants for casual wear. Sweatpants and sports shorts, on the other hand, should be avoided. Keep these for working out.
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Step 2
Browse through your shirt selection. Shirts are a little more forgiving. The first step is to look if it has sleeves. No sleeves means not casual, and you should skip them (for men as it is generally acceptable for women). Make sure the shirt fits. A shirt that is several sizes to big will look more like sleeping wear than casual wear. The casual shirt you want fits properly and is free of stains and holes. This can go from T-shirts to polo shirts. Button-downs can be fine until you begin tucking them in. This will change your entire outfit from casual to business casual.
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Step 3
Pick out a pair of shoes. For the most part, if they are free of holes and are not grungy shoes you would paint your house with, you'll be fine. However, shoes or extremely tall high heels you would wear with a suit should not be used. Yes, they may look nice, but they probably aren't comfortable. Comfortable is the key here.
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Step 4
Deciding on a hat can be a little more tough. It depends on the situation. Generally speaking, a hat can be acceptable for casual clothing, but you have to adapt to your surroundings. Wearing a hat outside or in your own home is fine, but once you begin wearing a hat inside of a restaurant while you eat, this can be considered rude by some, and place you in the same category as the guy who showed up with sweatpants and a cut-off T-shirt. This is a group you will not want to be placed in, so avoid hats at restaurants. Outside of this situation, you should be fine.
