Don't be afraid! Makeup should be fun and you can absolutely wear *whatever* at all you want, but if you're just starting out you may want to consider understated things and eventually get to bolder colors (if you want to!). I'll go with products I've tried and which I felt acquitted themselves well.
I think this might be the scariest area for people - eye makeup is the place where you can use just about any color you like (there are blue and green lipsticks, but most people find that unwearable whereas blue or green eyeshadow shades are considered a bit more 'everyday'). To start out, I would recommend an eyeshadow palette with both neutral (brown, gold, taupe) and brighter colors (blue, green, pink). Neutral eyes tend to look like these.
At the drugstore level, I'm afraid most eyeshadow is dreadful, but there are some exceptions! At the mid-end, I'm unimpressed with MAC and NARS while very impressed with Urban Decay and Illamasqua. I avoid Korean and Japanese eyeshadow at any price point other than Shu Uemura (which is amazing), since they tend to be pigment-free glitter bombs. I don't think it's necessary to splurge high-end here, as the quality isn't too removed from the mid-end, but a lot of people swear by Tom Ford and Burberry eyeshadow palettes.
- Drugstore! Sleek i-Divine in Storm or Au Naturel; Maybelline Color Tattoo in Barely Branded, Inked in Pink, Bold Gold, Bad to the Bronze; NYX Love in Rio palettes.
- Mid-end! Illamasqua palettes in Empower, Complement, or Neutral; Urban Decay Naked Basics; bareMinerals READY Eyeshadow 4.0 in The Truth, The Rare Find, or The Happy Place.
- High-end! Le Metier de Beaute Kaleidoscope Eye Kit in Bauhaus or Carnaby Street.
- Gel: Catrice, Maybelline, L'Oreal, Kanebo KATE.
- Pencil: Revlon Colorstay Eyeliner.
- Gel: Bobbi Brown Long-Wear Gel Eyeliner, MAC Fluidline in Blacktrack or Blitz and Glitz, Illamasqua Precision Gel Liner, Clinique Brush-On Cream Liner.
- Pencil: MAC Pearlglide Intense in Lord it Up or Black Line, Urban Decay 24/7 Eyeliner in Perversion or Zero.
The first thing I recommend almost anyone is Clinique Almost Lipstick in Black Honey, since it's moisturizing *and* the color's just about universally flattering. You might want a second lipstick for a brighter color, and you will *definitely* want to have a lip balm around if your lips are prone to chapping, or you want to wear matte lipsticks (which are, very sadly, almost universally drying....).
- Drugstore! Revlon Lip Butter in Peach Parfait or Cherry Tart, Maybelline Color Whisper.
- Mid-end! Too Faced La Creme, MAC Mineralize Rich, Clinique Almost Lipstick in Black Honey, Clinique Chubby Moisturizing Lip Color Balm in Mega Melon.
- High-end! YSL Rouge Volupte Shine (I can't recommend this enough, it's perfect - pigmented *and* moisturizing *and* long-lasting, just the best and honestly worth the price) in Corail Incandescent or Pink in Devotion.
This one's a bit complicated because people have different kinds of skin. If your complexion is darker - like mine - you'll have to gravitate toward the more expensive end of things, as mid- to high-end brands tend to have greater shade selections, and getting a shade match can be tricky. The basics is that you want to moisturize first before putting anything on your face.
I can't stand heavy-coverage liquid foundation for long and so I tend to go with sheerer formulas, or just wear powder with tinted moisturizers underneath. It depends on how much coverage you want! For drugstore, Bourjois and Revlon are quite good; for the high-end, Guerlain Lingerie de Peau is brilliant. I've heard good things about the Chanel Aqualumiere for those with dryer skin. If you want a foundation powder and want to go high-end, absolutely *nothing* beats Chantecaille Compact Makeup.
Blush is easier though! As far as that goes my recommendations come down to two things: for drugstore, Sleek Blush by 3 palettes. For mid-end, Clinique Cheek Pop Blush.
Please don't try applying your eyeshadow with your fingers or flimsy sponge-tip applicators that come in palettes! They are simply the most dreadful and the easiest way to get frustrated with eye makeup and give up forever. Invest in eye brushes! The choices are very simple here. If you want higher end, you pick up a MAC 239 and a MAC 217. If not, pick up a Real Techniques starter set. The basics is you use a flat brush (like MAC 239) to deposit eyeshadow, then a soft fluffy brush (like MAC 217) to blend it.
Face brushes I find fairly optional. Sponges like Beauty Blender are the most beginner-friendly for liquid or cream foundation, but for powder products applicators included in the compact or tin tend to do just fine.
In summary, broadly I'd say you want these things.
- Eye stuff. Eye primer, eyeliner, and one eyeshadow palette.
- Lip stuff. Two lipsticks - one a 'nude' or understated color, one a louder, bolder color. Have a lip balm around.
- Face stuff. One liquid foundation, one finishing powder, a blush palette.
- Tools. Eye brushes - one for depositing color, one for blending. Face brush - I think broadly you can just get one that can multi-purpose; face powder things tend to come with their own applicators (sponge or puff), liquid foundation you can use your hand.