I would go to sephora, tell them the look you want, and let them make you up. Then buy what they recommend. Or write down what they recommend, bring the list here, and ask for less expensive suggestions. It will be hard for us to make good suggestions without knowing what you look like.
Start small and add one item of make up when you feel like you mastered something. Also watch plenty of YouTube videos for inspiration.
For example, I started foundation and it took me a couple of tries to find the right shade. Then I added eyeliner and kohl pencil. Then I decided to add concealer to cover up dark under eye circles and zits. Then came powder, blush and bronzed.
I use liquid foundation. I have fair skin, blue eyes and dirty blond hair. For shadows I use a shimmery pink, gold or beige color on the lid from the lash line to the crease then a brown of some kind from the crease up. Mascara goes a long way. I don't know about drug store brands, I have a mix of Clinique, Urban Decay, and Benefit.
When matching your foundation I think you're supposed to match it to the color on your jawline. If you go to Sephora or a dept store counter they can find the right shade for you but I think that's how you do it yourself.
First of all, I think it's great that you're thinking about yourself, and doing things to make you feel good about you.
I know you want to start simply and at a lower price point since it's all new, but the one issue I have with drugstore makeup is that you can't try anything on, and so you may waste more money buying things that when you get them home you don't like.
Personally, I just started using a BB cream. I went to Sephora, was honest about budget, how much time I wanted to spend on my makeup, and how much I was comfortable wearing. We tried a few different BB creams and tinted moisturizers and I found one that worked really well for me. And it is SPF 45 so I don't need to do a separate sunscreen on days I won't be outside too much.
I feel more pulled together if I do a BB cream/tinted moisturizer, blush, mascara and then either brow powder or pencil. My face looks so much brighter when I do my brows - I find it makes more of a difference than any other makeup. I will often do more than that, but if I'm leaving the house I usually at least do those 4 things.
Our target sometimes has make up "experts" on the weekends that help you pick out make up. Maybe your's does? There is normally a sign at the pharmacy that says when she will be in.
I would go to sephora, tell them the look you want, and let them make you up. Then buy what they recommend. Or write down what they recommend, bring the list here, and ask for less expensive suggestions. It will be hard for us to make good suggestions without knowing what you look like.
Yes.
I can list all of my make-up, like I've done a million times, but the options would be so overwhelming. I've had good luck with Sephora.
I would start with blush, mascara, eyeliner, face powder, and maybe perhaps eyeshadow.
I hate face makeup. I have bought good stuff and cheap stuff but most of the time end up skipping it. So you can start there, but the biggest differences is in eye make up and and adding some color to your face IMO. Eyebrows also make a huge difference.
If I am going out in five minutes, I go for blush, translucent powder, and mascara then add from there.
You should go to Mac counter and to sephora. But a neutral tarte blush like exposed is probably a good place to start, and Mac blotting powder. I think you can go cheap on mascara. No need for expensive stuff, the orange cover girl tube is great.
Tritto Sephora. They'll help you find colors and products that will mesh well with your color and skin type. Figuring that out is half the battle! The products will cost a little more than drugstore, but at least you'll know it's the right stuff for you. That takes the guesswork out of things.
If I'm in a rush, I use NARS radiant creamy concealer, MAC bronzing powder, MAC mineralized skinfinish, Stila stay all day liquid liner and mascara (I'm a mascara hoarder). I'm currently loving Maybelline Rocket mascara in the blue tube. Its AH-MAZING! This takes less than 5 minutes.
Honestly, if you haven't done much makeup, I would start with baby steps. For me, my minimal thing is undereye concealer (I use Nars radiant concealer) if nothing else. Most of the time for a casual look, I add a dusting of a powder foundation (I use Tarte airbrush powder) a little blush, mascara and a light lip color (lip gloss or something like the Revlon lip color chubby pencils) . That makes me look awake but still super natural looking and not "makeup-y"