Hawaiian shirts are both fun and popular, but knowing what to wear with Hawaiian shirts will enable a person to avoid any fashion faux pas while still taking advantage of this unique warm weather attire.
Even before considering what to wear with a Hawaiian shirt the wearer should know how to wear one. The size should be loose-fitting but not baggy. Material will vary from cotton, to rayon, to silk, with many of the high end clothing manufacturers now (i.e. Tommy Bahama, Ralph Lauren, etc.) opting for silk. Due to the warm climates in which they are traditionally worn, silk and cotton are preferable to man-made materials, due to their breathability.
When fully buttoned up, the wearer should be able to fit two fingers between the neck and shirt collar. However, even if the shirt can be buttoned all the way to the top the shirt is normally worn with at least one and often the top two buttons left loose. The sleeve should stop just above the elbow and the hem 4 inches or so below the belt line. While some people prefer to wear the shirt tucked in, in Hawaii it is a sure sign of a tourist with the traditional method being untucked, signifying a relaxed, care free way of life.
Accessories should be kept to a minimum when wearing one of the bright, colorful Hawaiian shirts so as not to detract from the shirt as well as not to clash. As far as jewelry, the classic look is to combine the shirt with the type of necklaces which you might see a native Hawaiian wear. The white, puka shell necklace is a classic look, with the white of the shells serving to emphasize the shirt rather than to detract from it. For a woman, pearls also emphasize the features of the shirts, with their nautical history keeping with the island theme.
The ultimate "don't" for accessorizing patterned Hawaiian shirts is to wear anything that is of a different pattern. Neutral, single colors are the way to go as opposed to striped, paisley, or any other type of patterned material. As far as pants, long or short pants of denim material are always appropriate with Hawaiian shirts, although they are often too warm to be comfortable. Khakis, whether long pants or shorts, are traditional in tan or olive colors or whatever does not clash with the colors of the shirt.
Hats can also be worn with Hawaiian shirts. While baseball caps are popular, if one is worn it should be one that is plain in color and without an emblem. A Panama or straw hat is also a classic look. If a Panama is the choice, then a neutral color is best as would be one with a small hatband that has little or no pattern.
Footwear is a lot more flexible. If the shoes match the type of pants, they will usually match the Hawaiian shirt. Flip flops are usually a good choice, particularly the leather upper end ones. However, many men aren't used to wearing this type of footwear and their discomfort will be apparent and at odds with the confidence that is required to "pull off" the Hawaiian shirt look. Another popular choice for footwear are leather topsiders. These shoes were originally developed for use in the boating market but are now available in a variety of colors and materials. The brown leather shoes with the traditional white or tan sole and a leather lace are a classic and the nautical theme continues the look sought with the Hawaiian shirt.
The wearing of socks with the outfit can vary. Most will agree that a Hawaiian short, khakis, and topsiders negate the necessity but if the wearer is uncomfortable with that ensemble then socks can be added in as long as they are also of a neutral color that will match the khakis and not clash with the shirt. Silk or a silk blend socks will continue the cool, comfortable feel that starts with the shirt and continues with the casual footwear.
A recent trend is for casual, tropical weddings. However, although it can be fun, it is generally agreed that the bright Hawaiian shirts should not be paired with a tuxedo. Instead, the same feel can be obtained, without sacrificing the formality of the occasion, by having cummerbunds and bow ties constructed of the same material as the Hawaiian shirts and then worn with a traditional tuxedo.