I generally prefer to keep things simple and wear solid colors in neutral tones or classic patterns such as stripes or hounds-tooth checks. However, I am a push-over for an amazing print or bold pattern (particularly in Spring and Summer).
So, what constitutes an “amazing print/pattern”? Most importantly, you should love and be drawn to it. Much the same way as you would be drawn to a particular piece of art. Does it “speak” to you?
Second, does the print/pattern contain some colors you normally wear? If you wear a lot of blues, then a printed silk shirt in navy/white/aqua/yellow is probably a good choice. However, if a patterned sweater is army green/chocolate/yellow, it may not be your best bet.
Third, what printed or patterned article of clothing are you considering? Swim trunks or shorts are an obvious choice for a print. However, sometimes a printed shirt is a great way to punch up a staid grey suit.
Prints and patterns tend to be memorable, so be cautious when buying an investment piece, such as a coat, in a print or bold pattern. However, sometimes there are exceptions to this rule. For example, I have an amazing woven, lushly patterned, multi-colored rain coat from Belgian designer Dries Van Noten which reverses to solid black. Depending upon my mood, I can choose whether to wear the pattern “out” or “in” and the coat is less limiting within my wardrobe.
Keep in mind, prints and patterns with darker backgrounds will tend to trick the eye into reducing size, while prints and patterns with lighter colored grounds, such as white, tend to have the opposite effect. Pattern direction can also trick the eye. If I had a dollar for the number of times I have seen a larger person wearing horizontal stripes…. not usually a good thing.