I've been wearing makeup regularly since junior year of high school. I'll save you the effort of doing the math: that's 27 years of experimenting and practice. It also means that I've had plenty of time to make mistakes and look ridiculous without suffering the consequences. It's not always the case, though, as I've learned from several comments and emails written by new and newish readers in their 30s and 40s who haven't been wearing makeup until recently, and find themselves more than a little overwhelmed.
Makeup can and should be fun. It's something you do for yourself, a personal ritual that involves playing with color and texture. Makeup is about feeling happy, enjoying pretty things, and for me it's also a way to center myself and prepare mentally for whatever is ahead. What it shouldn't do is put on extra pressure and add to your stress getting ready; or even worse: make you feel inadequate because you have yet to figure out how to draw on your eyeliner.
Here are some points to consider if you're an adult who's just starting with makeup:
1. Before you even apply the first drop of a color product: Are you happy with your skin? Evaluate your skincare routine and see if it needs revamping. I know it's a cliche, but good makeup starts with a good canvas. Chemical exfoliants, a good moisturizer, and an effective SPF make a world of difference.
2. Start small. Don't rush out to buy products from every makeup category. It's tempting-- I'm one of those slightly obsessive types who wants complete sets, by-the-book routines, etc., but when it comes to your face and to learning new makeup skills it's just too much to do all at once (not to mention expensive). Add items gradually.
3. Start with your eyebrows. I know, it's not the most exciting and shiny thing, but this seemingly minor thing can make a huge impact on the way you look without appearing too obvious. And it's relatively easy to learn. If you're a 40 or a 30-something, there's a good chance that at some point you've overplucked your eyebrows. Maybe they never grew back fully, perhaps you're still doing that (please stop!). Getting your eyebrows professionally shaped is a good idea for beginners, but you'll want to do regular maintenance yourself. Unless you've never touched them AND that you're naturally well-endowed in that department, you'll probably need to gently fill in sparse spots in your brows and thicken them a little. Avoid pencils. Use a brow powder or even an eye shadow in a brown-gray color (for most brunettes. Redheads should go with an auburn and blondes are usually good with ashy colors) and an angled brush.
4. Avoid counter makeovers. It looks easy: you go to Neiman, choose a shiny counter, let the well-meaning SA go to town on your face and end up A) unrecognizable, B) $300 poorer, and C) still unsure how to get the look you're not entirely sure you like. It's one thing to go to the counter to learn how to use a specific product you already know you want, such as tightlining with a cake liner at a Laura Mercier counter, but don't get sucked into highlighting and contouring just yet.
5. Speaking of makeup counters, when you do go there look at the sale associates and makeup artists and approach the one whose makeup look you admire. Avoid anyone whose sporting something you dislike-- what are the chances she shares your aesthetics? Also, state in advance exactly what product you want to try and stick to your guns. "May I also show you this wonderful cream highlighter and our new blush and 60 color eye palette? They'll make you look taller!" "Thank you, but not today. I just want the mascara".
6. While there's a school of thought that says beginners should buy the cheapest stuff to practice and experiment, I find that after a certain age this is counter-productive. You won't learn how to apply foundation when using something with a patchy texture, and your brush work will not improve if you use inadequate ones that don't distribute the color evenly and don't blend. You'll only end up frustrated. Buy one or two items at a time, but invest in the best you can afford. You'll get better results and much more enjoyment.
7. Don't be tempted with full sets-- of brushes, of eye makeup, of anything, really. There are always duds, fillers, or simply stuff you don't need, so you're NOT saving money. You're actually paying for items you'll never use. Pick and choose your items a-la-cart. You'll get three brushes instead of ten, but these are the three you'll end up using every single day.
8. Despite marketing hype or various misconceptions, there's no such thing as a color that fits everyone. I know, they told you that NARS Orgasm blush is universally flattering. I assure you that it's not (not to mention that it has far too much shimmer which you might not like). You also read that taupe is the most perfect eye shadow color that looks great on everyone. Sadly, it's not. This elusive grayish brown color is beautiful on many people, but if your skin has a very strong yellow undertone it might not be a good fit. Don't feel like a freak and don't force it.
9. Shapes and techniques are also not set in stone. Your bone structure might rule out certain "standard" items. Some eye shapes (such mine: very deep set) make doing a regular"kitten flick" pretty much impossible, so you might need to adjust. I extend the liner straight out instead of upwards, and enhance the shape I create with a dark eye shadow. Or maybe you have such high cheekbones and hollowed cheeks that you can actually use reverse contouring instead of the regular technique. Which leads us to...
10. Contouring in everyday life is neither mandatory nor is it recommended. It's a great trick for photos, but it doesn't look natural face to face, and requires way more product than you probably want to be sporting. You see all these photos of perfectly made up people, but looking pretty and polished in real life doesn't mean Kardashianed.
Bonus point: YouTube is a great place to find makeup tutorials and learn some useful secrets from makeup artists (if you only subscribe to one, make it Lisa Eldridge). However, the fact that a person has a video camera and enough free time to upload and maintain a beauty channel does not always make them a reliable source of information. Go with your gut and don't feel compelled to follow the advice of anyone who calls herself/himself a "guru". B.K.S. Iyengar is a guru. The 19 year old with 3lbs of fake eyelashes is not. Also, remember that bloggers and vloggers outside of the US are not required to disclose sponsorships and affiliations, and most of them don't mention a word of such thing.
Photo of the divine Christy Turlington via Tatler, UK.