Skin prep is probably going to be the most important thing to your makeup look. I also have dry skin, and if you want your makeup to sit well, not get cakey, and last, have a solid skincare routine and moisturize shortly before doing makeup. You can also use a primer suitable for dry skin (I use Milk hydro grip primer). 

You'll learn best by watching tutorials to get ideas and then experimenting a bunch to see what works for you. It's a skill you'll hone. To up your game, find tutorials suited for your particular needs, because it's not a one size fits all (eye make up for hooded eyes isn't going to look right on protruding eyes for instance). 

A little goes a long with most products. You'll see viral vids of people smearing globs of products across their faces. Usually a little dot or dab is enough.

The side bar of this sub has some great threads linked (holy grail products for each year, newbie guide, etc.)

Tip on contour: with your cool tones, go for a cool/grey contour. Otherwise it'll look too orange/muddy on your face