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I wouldn't suggest doing it with slacks or more formal khakis and pants.
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Hmm..what about with chinos? I was reading an AskMen article earlier about different types of pants because I never understood the difference between khakis and chinos (I am bad at stuff like this but thanks to this thread hopefully getting better!) and the author mentioned that chinos are considered a tad dressier than just normal khakis.
Also I was thinking if there is anything specific you should look for in a dress shirt to do this. For example, don't some dress shirts have the back longer than the front?
Little off topic, but I've been browsing Banana Republic's website lately (thanks to this thread) and see they are offering 30% off on jeans. Seems like a nice deal looking at the normal prices of their jeans.