The standard wardrobe choices for men for social events is simple and stale: pair of jeans, short sleeve/long sleeve shirt and dress shoes. Walking into a restaurant for a happy hour or to an outdoor bar and grill, every man will look the same and women vary in their dress. Men can also do so and they do not have to feel that they are too feminine or "metrosexual" by wondering what they will wear. That is why men depend on "staple" pieces in their wardrobe--items that make them feel comfortable categorized by the occassion. A man may have a favorite shirt for work that he looks good in and doesn't pull or feel uncomfortable. He may have a short sleeve knit button down shirt that he likes to wear when he goes on vacation to a tropical location and a watch to go hiking and one to go out at night.
A man shouldn't worry about going outside of his comfort zone when going out.
He should start slow--
- try on pieces of clothing in the current wardrobe that haven't been worn in awhile.
- focus on texture whether it is thick fiber or poly-cotton--if you like how it fits but not the texture, try to buy another piece similar.
- Don't be afraid of a little bit of color--it doesn't have to be flamboyant but there could be one piece with a color that breaks from usual browns, blacks, grays, dark green and blue.
If there aren't good pieces available in one's closet, then grab a pen and pad and write down things you want. Then, jump online and begin to web search any and every store's line. Web retail can help men who really just want to buy the items and not have to wade through the pitch of an eager salesperson. Also, low-end retailers like Target, Walmart and KMart have good clothing pieces which are good economic choices. The conclusion would be that going out won't be tiresome and boring depending on how good the locale you are going will be that night and will break the boredom of choosing the same wardrobe pieces each time.