Beauty Q&A: Sexy in Specs, Skin Picking, and the Secret to All-Day Makeup

I’ve worn glasses since I was nine years old. I like my glasses, but have never learned how to do eye makeup properly because of them. I’ve put on eyeshadow, eyeliner, and mascara a few times over the years but once I put my glasses back on it all just looked wrong and old-ladyish, somehow. Nowadays, I will put on a little mascara, but I usually do nothing. I want to play with color and shading! Is there a way for eye makeup and glasses to look great together?

This is one of the most common questions around here and, luckily, there is an answer! Do whatever Tina Fey does. Copy her whole life! But seriously folks, the first thing to keep in mind is that your glasses are a look already, so you don’t have to do a lot to draw attention to your eyes. Now that half the work is done, there are four key elements to nailing a hot eye makeup look behind glasses: groomed brows, a light shadow, fun eyeliner, and bold lashes. You’re putting a literal frame around your eyes, and, when done well, eyeliner and mascara can make your eyes look ridonkulously huge and sexy behind glasses, like Michelle Trachtenberg over there. Wearing a complicated or too-colorful shadow combo under specs tends to push the look over the top, so unless you’re a pro, don’t bother.

First, here’s a video that will help you with your brows, the original frames your face came with. Next, after applying some eyeshadow base (my standby is Laura Mercier’s Eye Basics in Linen), sweep a light neutral color across your whole lid. I like Stila’s eyeshadow in Sun or Smashbox’s in Butter. It’s your eyeliner that is going to define this look so decide whether you’re going for drama — in which case you’ll want to do either a liquid liner or a smudged look with black liner on the waterline — or a more natural look that just calls for a little bit of dark eyeshadow smudged into your upper lash line. Here’s more on that. Finally, curl your upper lashes and apply an ass-ton of mascara. Like two or three coats on top and one coat on your bottom lashes. My fave is Maybelline Full ‘N Soft. Now channel Christina Hendricks and try not to get knocked up immediately.

I am a compulsive skin-picker (see: When I get blemishes, it’s damn near impossible for me to not pick the shit out of them over and over till they bleed and eventually heal and probably scar. I’m 20, so I’m still vaguely acneic, and additionally, I get cold sores on my chin (I know, what even?) that I also tend to irritate. So I have a few questions: What products should I be using to minimize the damage? My current regimen includes Murad’s line of acne stuff, plus tea tree oil on healing spots, and the occasional bandaid with Neosporin at night. Is there a way I can expedite healing for my various scabbed-over blemishes besides antibacterial ointment and time? And can we talk about cover-ups/foundations/etc. — ones that work on rough, kinda fucked-up skin? Also scars: How can I prevent them (obviously I should try not to pick, but you know, in the meantime)? I tend to just wear my sores without makeup lately but sometimes I just want to not deal with how the spots look against red lipstick, etc. Also, I just got a real job, so I’m willing to drop a little bit of coin on quality products. Any help would be really appreciated!

Oh boy, I feel you. I used to do this way back when I was your age too. I’ve gotten a handle on it so that I’m no longer Chicken Poxy 100% of the time, but it is a constant temptation. Let me start by putting bluntly what is happening: You pick at bacterial, and sometimes viral, infections on your face until they bleed and then, because of the compulsion, you move on to the next one without washing your hands and face, thereby spreading the problem around and then you cover the sores with various products that don’t fix the problem. It’s a never-ending, terribly harmful and painful cycle and it breaks my heart that you are going through this. If I were there I’d remove all the mirrors from your house and duct tape mittens on your hands, probably, but that’s because I’m not a medical doctor. And I hesitate to recommend an over-the-counter product or makeup because those are temporary fixes at best, exacerbating the situation at worst. Instead, allow me to give you some assignments for “the meantime” and if you can tough it out, we’ll talk makeup and stuff in a few months, OK? Baby steps!

Find a reputable therapist who specializes in treating anxiety disorders and make a commitment to yourself that you’ll go as often as they say is needed for you to get a handle on this. Therapy and a dermatologist are where you should spend your new dough, not Sephora. And don’t be afraid to try medication if that’s what they recommend. Who knows? You could take one tiny pill and be in a whole new world!

Ask your doctor about getting some antibiotics to treat your acne. I had the best luck with generic oral minocycline, but you may prefer a topical antibiotic since they can be applied right to your skin and will feel more like you’re actively treating the problem, nahmean?

Start obsessively drinking water. When you find yourself heading toward a mirror, stop and drink a tall glass of water and wait it out for a few minutes. Seriously, just make yourself do that and don’t beat yourself up if you still end up picking. At the very least, getting more water in your system is really going to help the condition of your skin. At most, you’ll adjust your usual patterns of behavior and possibly pick less.

Once you get a better handle on this, ask for a prescription for Retin-A to start repairing your scars and further help control your acne. Another scar-minimizing but not too too expensive treatment is a TCA peel. Only go to an actual doctor’s office for this. I’ve had one done and it totally got rid of dark spots and made my skin a whole lot smoother. It’s a strong peel and noticeable for about five days so try to plan it over a long weekend when you won’t have to go in to work. Let me know when you’re on the mend and we’ll go to Sephora! Oh and also: Getting cold sores in unusual places isn’t actually all that unusual. Human bodies, am I right!?

I seem to keep running into one serious problem, which my boyfriend has lovingly termed “raccoon eyes” …yeah. Whenever I wear mascara (or eyeliner, or darkish eyeshadow), I end up with dark rings under my eyes by the end of the work day, where the whatever-the-heck has fallen down throughout the day. And yet other ladies seem to make it though the day flawlessly! What’s their secret? How can I avoid the awful raccoon look? Do I just touch my eyes a helluva lot more than normal people?

You might! But I bet that’s not the problem. It might be that you’re wearing a mascara that tends to flake off, in which case try switching to a higher quality formula. This will involve some trial and error, but that’s what Sephora’s lax return policy is for. As far as everyone else looking un-raccoon eyed? I’m going to tell you a secret: Many women, including me, reapply our makeup throughout the day and we don’t tell anyone we’re doing it. We just sneak off to the bathroom with our makeup bags. I don’t take all of my makeup off and start from scratch, but I do wipe smudges from my lids and under my eyes, reapply shadow and liner if needed, freshen up foundation where my zits have begun to show, and then re-up my blush. I usually do this around lunch time and then again before my train ride home. Is that where you see me and wonder how I got my makeup to stay put all day? Sucker.

If you’re opposed to putting in those man hours, you may want to consider a super-sticky eyeshadow primer that should at least keep your eyeshadow and liner in place a bit longer. Urban Decay’s Eyeshadow Primer Potion is like fucking rubber cement or some shit. I kind of hate it but it works. Just beware that it grabs onto pigment in a serious way so start with less shadow than you’d normally use and build to the look you want.

I’m getting a little bored with my hair so I’m thinking about dyeing it. Mostly, I haven’t done this yet because it’s expensive and also because I can barely handle getting regular haircuts, much less getting my roots touched up or whatever. I’m mostly over those things, but there’s one other thing that’s stopping me: my hair is very fine and very blonde. I’ve heard all these urban legends or whatever about women with blonde hair dyeing it and it, like, changes color permanently and is never the same, and that would make me SO SAD. Is this a real thing?

No, dyeing your hair and it permanently changing color is not a real thing. Dyeing blonde hair at home and having it turn out not exactly as the box indicated IS a very real thing, however. I don’t know the science of it, but some blonde hair grabs pigment in a weird way and you can end up with an unintended or uneven color, even if you go for a high-end dye. This is especially true if your blonde is the result of highlighting or previous dye jobs. The only way to be sure to avoid this is to see a pro and let them do the first round of color. They may need to use what’s called a “filler” on your hair. Filler re-pigments your hair and preps it so that it grabs color evenly. After that, since you’ll just be touching up the roots, you may be able to get away with doing it at home every-other time. Just ask your stylist what they’d suggest if you really can’t afford the time and money to always go back to the salon. Be honest, you know? Just say, straight-up, “I’m sorry I cannot afford to come back here every 6–8 weeks but I don’t want to do something that makes your job, every four months or so, a total pain in the ass because you’re forced to correct my mistakes. Is there a product I can use in the in-between times that’ll let me eke out another month or two of your amazing work?” They may suggest you go for a temporary color like Clairol’s Jazzing, or one of those lipstick-looking things that seem totally grody, or they might trust you to use a permanent product like Root Touch-Up, or they may tell you to go fuck yourself, which is not very nice but it is a possibility!

And finally, some homework for everyone:

Ladies, let’s all get teasing combs! Like this one or this one or this metal one that my bestie’s mom has been using to magical, gravity-defying effect for decades. I’ll show you some cra-mazing things to do with it in the next video, but you have to give me a minute because in a few days I’m packing up all of my belongings and driving across this great land to resettle in Los Angeles, California!

Previously: Longline Bras, Feminine Style, and Blackheads.

Jane Marie produces the radio program “This American Life,” and no one pays her to say any of this. Do you have a question for Jane?