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One thing I can recommend is buying one of the good books done by noted makeup artists to give you an idea of where to start. Bobbi Brown has a good one (
The Bobbi Brown Makeup Manual) and it deals with all ages, all skin colors, all ethnicities, and so forth. You can usually find a used copy on Amazon for $10-15.
You could start with simple things, and work into the more complex ones, to make it less intimidating. A very basic no-makeup 'I woke up like this' look involves a BB or CC cream, a tiny bit of concealer if needed, brow grooming, a touch of mascara, and tinted lip balm a half-shade darker than your natural lip color. You can also add a neutral matte eyeshadow close to your skin color for evenness if you like.
The biggest beauty asset is good skin and good grooming. A good moisturizer is essential. I always put a layer under my other makeup, with a few minutes taken between those two steps to let it sink in. A lighter formula is better for under cosmetics, and a good one doesn't have to be hugely expensive. Brands like Paula's Choice offer really good products at reasonable prices.
Once you start moving toward color cosmetics, you'll want to invest in basics first: A nude-colors eyeshadow palette, one blush that works well with your skin tone, two different lip products for day and night (one of which should be a shade darker than your lips for a good go-to color, and one that is a little darker or more interesting for adventurous days or nights out), and, if you want to use it, an eyeliner pencil or pen.
My own recommendations will be dependent on your budget. See below:
BB/CC: This is very much a personal preference, I will note. Neutrogena's tinted moisturizers (a lighter version of BB/CC) are decent for the price (around $9, I think). I like the Stila Stay All Day BB, but the colors offered didn't work for me at all. My go-to face product right now is the Bare Minerals powder foundation, but some people have problems with it settling into pores and fine lines. I don't, but I also use a primer.
Concealer: This entirely depends on how much coverage you need. I have hereditary dark circles under my eyes, so I use a heavy one, IT Cosmetics' Bye Bye Undereye. It's waterproof and very thick, so you will wind up needing to practice working with it to make it go well. Lighter choices abound, though for dark circles that aren't as bad as mine, Bare Minerals' Well Rested concealer is a decent choice. MAC has several options, and the ones I've tried have all been quite good.
Mascara: This is very much a personal choice. Everyone has different opinions on what a good mascara is, and how it works for them. I will say that the best way to try them out is to join a subscription box service like BirchBox -- you'll wind up with lots of samples to try out. I would avoid waterproof mascaras at first, because they can be difficult to remove until you're more practiced with doing so. I will, however, recommend an e.l.f. product that's a clear mascara on one side and a brow gel on the other -- the clear mascara can be used as a top coat over a colored mascara to keep it from bleeding.
Brow grooming: This just means plucking or waxing into a natural shape, and then combing the brows into position and using something to hold 'em in place if needed. Anastasia Beverly Hills makes two products that are great for people new to makeup: a set of brow stencils that you can use to shape your brows neatly when you pluck, and a brow gel to hold the hairs in place. If you have a store with a Benefit Brow Bar nearby, the price of getting them to do yours once so you can get a photo to use for guidance might be worth it, if it's in the budget.
Tinted lip balms are available in a wide variety of colors and formulas. For a budget option, NYX makes a product called Butter Balm which comes in a whole lot of shades, and retails for around $3. The brand is one of my favorites, and their prices are quite reasonable. Not all of their products are amazing, but there are enough good ones to make them worth trying. My absolute favorite tinted balm is from Clinique -- the tinted balm Chubby Sticks.
Blushes: NYX makes some very nice ones for a decent price. The Mosaic blushes are really nice, and there's a blush they have called Pinched that seems to be a pretty universal shade. If you're fair-skinned, you'll want to apply with a light hand.
Moving into the more advanced part:
A set of good brushes is crucial. There's a post somewhere around here with a list of the ones you need to start. If you want to buy a basic set for a reasonable price, the brand Real Techniques makes some very good ones. Amazingly, the budget brand e.l.f. makes some good-to-very-good ones for $3 each. They have two lines of products, and the ones you'd want are the Studio line. I actually use some of their brushes over my much-more-expensive alternatives.
Also, primers. A primer for makeup is just like a primer for paint in your house: It prepares the skin for makeup and gives it staying power. An eye primer is, to me, the one that's indispensable. Face primers, lash primers, and the like are all useful, but all of these steps can be really intimidating for someone new to makeup.
NYX also makes a series of eyeshadows called Nude Matte Eyeshadows that are fairly sheer and very forgiving for new users. I own about six of the colors, several of which are great go-to colors for days when I want the basics. They can be a little chalky, but they're a good starting point. There are so many good brands of eyeshadows that it's hard for me to know where to begin, but the Urban Decay Naked Basics palettes are a good starter as well.
Lip products come in a variety of shades, formulas, and the like. I can't even begin to summarize here.
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The most important thing is to try things out at home before going out in public, and feeling at ease with application. I still stink at using eyeliner, 30+ years after I started wearing makeup. Sometimes it won't be perfect, and that's okay. Learning to correct mistakes is as important as knowing how to apply it in the first place.
