Moisturizer.
This helps keep the skin flexible and helps keep the foundation on the surface, so it doesn't develop that caked-on look, and (hopefully) will help prevent lines from forming in your foundation. A little bit goes a long way. I often use sorbolene cream, or even plain vitamin E cream, mixed with a tiny bit of water, but you might want to try a product that's specifically made as a pre-makeup moisturizer.
Beard cover.
There are various ways to hide beard shadow. The most effective beard cover products (eg Dermablend) work best with a fairly thick foundation. That may be ok for a glamourous evening makeup look, but they may be too heavy for a more casual daytime look, especially in the warmer months.
The old standby method is to use a cheap orange lipstick on the beard shadow. The orange neutralizes the bluish tinge that beard hairs impart to the skin. Cheap lipstick is preferred for this because more expensive lipsticks tend to contain moisturizers, which give the lipstick a thicker & richer look on the lips, but which aren't wanted for beard cover. You may need to experiment with different shades to find what works best for you.
You probably don't need to cover the whole beard area - just the areas that have noticeable beard shadow, like the chin, mustache and side-burns, and possibly the throat, if you have a very heavy beard. Your foundation and blush should be enough to cover the cheek areas.
Dot the lipstick over the area then blend it with a fingertip. Use a different fingertip to remove bits of lipstick that are not on the beard area, eg just above & below the lips. Use enough lipstick to make it look like you've got a mild case of sunburn.
You are not just trying to modify the colour of the beard area, you're also attempting to make it look smoother by disguising the dottiness of the beard hair follicles.
Concealer.
Concealer isn't essential, but it can certainly be helpful. I love pale green concealer.
It's excellent at hiding red blemishes and it can also be applied (very lightly) over the beard cover to achieve a more natural colour balance. A thin zone of concealer around the lips can be blended into the beard cover to make sure that the beard cover isn't touching the lips. This will also improve the contrast of the lips themselves.
Foundation.
Traditional foundation is a liquid, although in recent years powders (eg, Bare Minerals) have become very popular. Powder foundations are good for a light "no makeup" look, but they may not work so well in conjunction with a beard cover, although you may like to experiment with them. If so, you might like to try using an orange-y blush powder as a beard cover instead of the orange lipstick.
Modern liquid foundations are water-based, so they are a lot lighter than the old-fashioned oil-based formulations.
Liquid foundation can be applied using the fingertips, a sponge, or a brush. I mostly use a sponge, and when I'm finished applying and blending it I also go over it with a clean dry sponge (or brush) to remove excess.
Apply foundation to your whole face and throat, blending it at the sides and base of your neck. Don't forget to put some on the front of your ears and your forehead.
Powder.
Pressed (or loose) powder is normally applied on top of liquid foundation. After applying your foundation, wait a minute or so for the foundation to dry out a bit before applying powder, but the powder does help the foundation to set; it also improves its optical qualities, making it look more natural. Cover all of your foundation with powder
except your lower eyelids - powder here can make the lower lids look wrinkly. After applying the powder, brush off excess. Try to keep the brush strokes vertical, preferably going in a downward direction.
Eyebrows.
Eyebrows are tricky. If you intend to go full-time you'll probably want to pluck or wax them, to give them a more feminine shape. At this stage, you might like to experiment with eyebrow pencil to make the texture more even and slightly darker, but I advise to not worry too much about them at this stage, at least until you feel very confident with doing eyeliner.
Eyeliner.
As Virtual_Aardvark said, a grey or brown eyeliner pencil is probably the best for your skin & eye colours. Also, a mistake is easier to clean up with a grey eyeliner than with an intense black one. Try to get a smooth even line as close to the lash line as possible. After you've drawn the liner on you can go over it lightly with a cotton bud to smooth it out and smudge it, giving a softer effect. Also use the cotton bud to clean up the outside of the line (ie the opposite side to the lashes) and to fix any mistakes.
It can be difficult getting the accurate hand control required to draw the lines you want, especially at first when you're a bit anxious about having a pencil so close to your eyes. You can make your hand steadier by cupping the elbow of your drawing arm with the palm of the other hand. You may also find it helpful to not hold your head totally still but to rotate it slightly while drawing, thus sharing this tricky coordination task between your hand and your head.
Different brands of eyeliner have different textures. You may have to try a few different brands before you find one that works smoothly for you and that interacts well with your foundation. Also, eyeliner is temperature sensitive. An eyeliner that applies smoothly in winter may not work so well in summer: it'll stick and jump, creating a dashed line instead of a smooth line. Some people combat this by putting their eyeliner pencil in the freezer for at least half an hour before use.
Several posters in this thread have mentioned liquid or gel eyeliners. They are good, but they're a little harder to apply neatly, and IMHO a pencil is better when you're trying to achieve a subtle effect.
Eyeshadow.
The standard approach is to put a light shade above the eye crease, blending up to the eyebrow. Then put a dark shade in the eyelid crease, and then a medium shade on the eyelid itself, with a thin line of the medium shade just under the eyeliner on the lower lid. I like to use shades of brown, and even if I use another colour I still use the browns as a base and blend the other colour on top of the medium brown.
I normally apply my eyeshadow using the small sponge applicators that are often supplied with the eyeshadow, but I use a fine brush to blend it nicely.
Mascara.
Mascara is a bit fiddly, but it's totally worth the effort.
I won't go into details here, since it's already been adequately discussed in the thread.
Blush.
Blush (aka rouge) is easy to do. It adds depth and colour to the face. It's also easy to over-do. If you already have pronounced cheek bones, proceed with caution.
Once again, practice makes perfect.
Lip liner and lipstick / lip gloss.
Lip liner gives definition to the lips, and also makes the task of applying lipstick or lip gloss easier, by giving you a solid line to work to. Lip liner is a bit easier to do than eyeliner, but it still requires practice to get it smooth and symmetrical. First, line your lips. Next, apply the lipstick or lip gloss. Then use the liner again like a paintbrush to blend the lipstick or lip gloss to the line. Now smudge your lips lightly on a tissue to remove excess. Be carefully not to rub, or you'll smear your lippy! If you like, you can now set the lippy by carefully applying some pressed powder around the border of your lips, re-apply the lip liner (and possibly the lippy) to cover areas on the lips themselves that got powdered. At this stage, I like to finish off with another application of pressed powder over my face (avoiding the eyes, of course). This makes the blush a bit more subtle.
Ta da! You're finished. Almost. Now it's time to paint your nails.
And don't forget to dab on some perfume...
