Regardless of the portrait style you desire, there are several basic clothing and accessory choices that can result in improved portrait results. Likewise there are several choices of clothing and accessories that can detract from the quality of a portrait.
Clothing tops (shirts, sweaters, jackets, blouses, etc.) should be either quite dark or quite light in color. This allows the top to readily stand out against a contrasting background. Intermediate colors don’t produce this same rich contrast and should be avoided if possible. Also consider wearing a top that has an interesting collar and/or sleeves. These help frame the hands and face and provide a distinctive appearance to your portraits. A top that has interesting textures (e.g. a sweater) can also add depth and richness to an image. Avoid tops that have busy colors, stripes, and noisy patterns as these often do not reproduce well on film and can distract from the real area of interest – you. If you will have more than one change of clothing for your session then consider bringing a variety of necklines, textures, colors, and undergarments to achieve a wide variety of looks.
A couple of other pointers regarding colors. Darker colors have a somewhat slimming effect in a photograph. Lighter colors can have the opposite effect. You probably want to avoid clothes that will cast a reflective color on your skin tone. The camera will readily pick up this reflected color cast and render you somewhat off color. Bright reds, yellows, and oranges are common colors that can produce a color cast. Think in terms of soft or pastel colors and you should be OK.
If your portrait session will involve images beyond just head and shoulder images, then all that is generally required for the bottom is a pair of blue jeans, dark slacks, or similar clean clothing (depending on the style of the portraits you desire). A nice pair of dark shoes also reproduce well on film if your portrait session will include the feet. Please bring shoes that are appropriate for the clothing you will be wearing. Tennis shoes with a suit may be a fashion statement, but it will probably look pretty dated in just a few years. If you plan to have more than one change of clothing, please ensure that you bring shoes (and socks or stockings!) that go with each planned change of clothing so that we are able to do full length pictures of each outfit.
Avoid clothing containing logos, slogans, or other distractions. Years from now you may regret an image that prominently displays the logo of a company that has long been out of business or that has gone through a major scandal.
If you wear jewelry to the portrait session try to keep it simple and elegant. Too much jewelry or jewelry with overwhelming proportions draws attention away from the subject of the photograph. Simple and elegant are generally the watch words when selecting jewelry for a portrait. The same applies for any other accessories that you wish to have included in your portrait.
Glasses represent a particular challenge in portraits. The lenses tend to distort the face, producing a less than pleasing effect. Consider bringing a pair of frames without lenses or be prepared to remove the lenses from your existing glasses. You might also consider a portrait without glasses. In general we know that you will not be pleased with portraits taken through the lenses of your existing glasses, so please be prepared to have your portraits taken either without glasses or without lenses in your frames.
The above discussions offer some general guidelines regarding what to wear and what you might avoid. In truth, you will look the best in your portraits if you wear something comfortable and in keeping with your sense of style. So, bearing in mind the above guidelines, wear what makes you feel the best, the most comfortable, and most like yourself.