Lipstick comes in a variety of types and colors. For transgender women and crossdressers, your type selection will depend mostly upon how long you plan on wearing your makeup. Your color selection comes down to the color of your eye makeup, and the color of your outfit. Lipstick should be applied after masking your beard shadow. You don’t want your foundation to go over your lip makeup.
Picking A Color
My suggestion for first timers is to buy a kit with various colors, and see what looks best on you and your favorite outfits. Avoid red as your first color, as it will likely not look good the first few times you do your makeup, since your makeup skills improve over time.
Purple lip stain, a great contrast for black colors.
If you want to avoid the expense of a kit, try searching what kind of lipsticks match up well with the kind of eye makeup and outfit you’re wearing. Some good example queries would be “what color lipstick matches smoky eyeshadow”. Another good query would be “lipstick match black dress”. I personally prefer to wear a dark purple lip stain when wearing all black. It provides a nice dark colorful contrast to the dreariness of black.
Picking A Type
There are many different types of lipsticks: Sheer, demi-matte, matte, gel, lip gloss, and lip stain. Each type has different properties. For example, a matte lipstick has no shine when applied to your lips. A demi-matte lipstick has some shine, while a sheer one would be shiny. Each type provides a different look, and they last more or less than the other types. Instead of basing your type choice around your outfit color, base it around how long you plan to be dolled up for.
A reddish/purplish sheer lipstick
Sheer lipsticks will be the glossiest of the options here, besides lip gloss. They will last less than matte type lipsticks, but longer than lip glosses will. So you’ll likely need to re-apply once or twice if you have a long night planned. Sheer lipsticks will have a moisturizing effect, in contrast to matte type lipsticks. So no worrying about applying lip balm beforehand.
A matte lipstick set
The word “matte” means a color without any shine or gloss. So matte lipstick would have no shine to it when applied. Matte lipsticks tend to last the longest. The drawback here is they tend to dry out your lips. So be sure to use lip balm before applying. Make sure to allow your lip balm to dry before applying.
A demi-matte lipstick
The prefix “demi” can mean half or partial. So a demi-matte lipstick would only be partially matte. This means it would have around half the gloss a sheer lipstick would have. Demi-matte lipsticks seem to last as long as matte ones. With that in mind, you should also use lip balm before applying this type.
A lip gloss set
Lip gloss is glossier than any lipstick, hence the word “gloss” in the name. It also has less pigment, giving it a more subtle coloration to your lips. As a result, it wears off quickly and must be reapplied regularly. This makes it great for a quick one time look, but awful for a long night out if you don’t want to be reapplying regularly.