Fit:  By far, the most important piece of the puzzle is Fit.  You can make a plain white button down shirt from the Gap look like a million dollars–if it fits you to a T.  But if your shirt doesn’t fit you quite right, it’s going to look cheap, even if you paid a small fortune for a designer brand. 

For button down shirts, look at how the shirt fits at the shoulder.  Most everything about your shirt (sleeve, waist, etc) can be tailored to fit you, but the shoulder is the one place where you can’t alter the shirt.  We recommend that the shoulder seam (the line of the shirt that connects the body of the shirt to the sleeve) should rest in the little gap between that little bump at the end of your collarbone and your arm. For more information on fit, read John’s tips on how to fit a button down shirt.

Color: Sure, you could go with a standard blue or white shirt, but why not find a shirt whose color suits you?  Be bold and try a different shade.  Try navy instead of traditional medium blue.  Reach for a royal purple shirt.  Or be really bold and try a salmon colored shirt.  Remember, getting dressed should be fun–make it that way with a shirt that’s completely you.