The first rule is “there are no rules”; however, have a reason for your clothing choice.  The clothes should complement the intent of the image.  Portrait photography is about you, not your clothes; however, when possible your clothing should provide some subtle context for the image without being a distraction.  Some choices are more obvious than others; an Executive Portrait will typically call for something formal.  Plan ahead and make clothing decisions based on what the portrait is for.

Consider who the portrait is for and where the portrait will be displayed and that should help guide your sense of formal attire vs. more casual.  Consider the color of your apparel choice for a family portrait and how it will work in the room décor where the portrait will hang.

Cover your skin with long pants, long sleeves, etc.  When you look at a portrait, your eye is naturally drawn to exposed skin and contrasting light.  Eliminate those distractions by covering arms and legs so the focus is on your face.

Clothes should be plain.  Patterns, logos, writing, pictures, lines, dots, contrasting trim and bright shiny fabrics will be a distraction in the photograph.  Interesting textures are fine.  A well composed portrait with the best equipment can quickly be overpowered by a poor clothing choice.  Avoid trendy apparel; tastes are specific and change over time. Don’t allow others to have a negative first impression based on your apparel choice.  Likewise, you will still enjoy your portrait for years to come if you avoid dating yourself with trendy apparel.

Colors: solid, dark(er), plain, warm or cool, pastels and earthy colors work best.  Wear something that compliments your skin tone.  Very dark fabric may not work on someone with very fair skin or very dark skin.  Pants and skirts should be darker than the shirt or blouse so the viewer’s eye always travels towards the face.  Layout your choices and see if your eye is drawn to any one item, if so change it because the same thing will happen in the photograph.

Black and white photography is shot as a color digital file in the camera before it is converted to a black and white image.  Consider how your choices will render in a black and white if that is your intent.

Bright white and dark black clothing are possible but they should be discussed beforehand to make sure they tie into the intent of the image.  Blacks and whites can create unnecessary challenges during post processing if the image needs to be brightened or darkened; details in the blacks and whites can be lost.

Kids can often be exception to clothing guidelines and likewise they should wear bright(er) clothing if the purpose of the image calls for something light and fun.  The same rules apply though for kids in group pictures.  Always avoid shirts with pictures, writing, logos, branding, etc…

Shirts:  Formal always works better than casual.  T-shirts and golf shirts rarely work.  Collared dress shirts and button-downs are preferred.  For women, v-neck or mock-turtle neck is ok but collars work best for ladies too.  A shallow v-neck will have a slimming effect whereas a wide open collar will have the opposite effect.  Bare shoulders, plunging necklines and exposed arms are all things that will distract from your face and really kill a good portrait.

Shoes and socks.  If the portrait will include your feet, wear something dark and plain.  Avoid white socks and trendy bright colored running shoes or they will take over the image and date it.

Accessories / Jewelry.  Other than wedding rings, do not wear jewelry without a clear purpose.  Will the item(s) help the image?  Will it be distracting?  Avoid big, flashy, colorful trendy items and anything that will contrast with your apparel choices.  Conservative choices like diamond studs and pearls are timeless and should remain fashionable years from now.  When in doubt, don’t wear it.

Glasses.  This is a personal choice you need to make.  If you are not easily recognized without your glasses you should consider wearing them.  If you correction is very strong, this could hurt the image if your face is distorted through your eyeglass lenses.  Reflected light in the lenses can usually be overcome.

Hair and Makeup.  Similar rules as clothing; keep it clean simple.  Hair should be styled conservatively.  Makeup should be neutral and even; pay special attention to eye makeup, too much can actually draw attention away from the eyes and to the makeup itself.  If you plan on getting a haircut, try and do it at least a week before the shoot.

Be comfortable.  If you purchase something new to wear for the portrait, try it on or even wear it for a while to make sure you are comfortable with your choice.  Nothing too loose or too tight so try on those pants you haven’t worn in a year.  The portrait session could last several hours, be comfortable.

Couples / Family Portrait Photography

These same rules apply with one additional and important requirement – your clothing has to relate to the other people in the portrait.  This does not mean “match”.  The apparel should be from the same season and the subjects should appear they are all headed to the same event.   Everyone can wear jeans and a plain shirt from the same color-family without matching.  For family portraits, there will have to be some amount of compromise on the clothing (theme) choice, so keep it plain and simple when possible.

Example, Husband and Wife: Husband dressed in a blue shirt and his wife wore a neutral color blouse with a blue sweater to tie them together and communicate “a couple” in the image without matching.

Example: Family portrait, each person looked great on their own and they each dressed according to their individual personality and taste.  The assortment of shirts were crew neck t-shirts, a long sleeve flannel shirt and a long sleeve (shiny) blouse.  As a group they were not headed in the same direction and the group portraits suffered because of the clothing.  To save these images we processed them in black and white to downplay the differences in apparel choices.

Google images of TV cast members and see how a dozen people in one photograph dressed differently seems to work.  We have all seen family portraits where everyone is wearing a white shirt and jeans; you may have one of those portraits yourself.  That is one way to do it but this idea is overdone, not my favorite and should be a dead-last resort.  Human beings are conditioned to (first) look at light(er) objects and exposed skin in a photograph.  You can never compete with a bright white shirt.  Go look at some of those white shirt family portraits and see where your eye goes.  The faces get lost in a sea of white.

The Environmental / Executive Portrait

This is a clear exception to the aforementioned rules unless you are able to work in some of the suggestions.  This type of portrait can be as much about your clothing and surroundings or place of work as it is about you.  Depending on the reason for the photograph, your options may be restricted by a dress code or industry standard or we may need to promote a specific intent for a commercial publication.  The message here is to plan ahead and communicate so we both know what to expect.

Conclusion

This is your portrait so wear what you want.  Portrait photography guidelines are simply suggestions to get the most out of the photography equipment and final image.  More times than not, these guidelines work but you have to decide how to present yourself and what you want the image to say about you.   Finally, have a backup plan with several items ready to wear in case your first choice isn’t working.