Reader question: What makeup should I wear with glasses? (Hint: Anne Hathaway pretty much nails it…)

I have a thing for glasses. (Especially, as anyone who knows me will attest, on the male population.) For women, they can be equally adorable—but as a glasses-wearer myself, I know all too well the beauty challenges of trying to “dress them up” when you want to wear something other than pajamas and lip balm. And then there is the not insignificant fact that you are unable to actually see, which further complicates the matter of makeup application.

Reader Melissa knows exactly what I’m talking about. She writes:

When I have contacts on life is great makeup-wise, but what to do about my makeup when I have my glasses on? They just seem to be a distraction from my eyes, and a huge off-balance to my face as a whole with proportions… I don’t really know what to do with my face — in fact I skip doing anything with my eyes entirely when my glasses are on.

Now, I know the temptation to throw in the beauty towel is great—but with the help of Anne Hathaway and a few other celebs, I’ve assembled some glasses guidelines for my fellow four-eyes:

LESS (MAKEUP) IS MORE

It really is.

I know the temptation is to overcompensate for the glasses by dialing it up—way up—with the makeup, but my personal opinion is that it’s overkill. Some prescriptions, yes, can make your eyes look smaller, and there are ways of dealing with that… but glasses just do not go with dramatic smoky eyes… or tons of colour all the way up the eyelid.

It’s kind of like wearing big earrings AND a big necklace. Even if you can pull off tons of makeup with your contact lenses, somehow throwing that additional accessory into the mix can make you look clownish. Instead…

FOCUS ON GREAT SKIN

Can you believe this is Megan Fox?

Her skin looks amazing here, and is a testament to this post about how to do minimal makeup while still looking polished. (Because believe me, even though this look is low-key, it takes some finesse with primer, foundation, illuminator and blush to get your skin looking this radiant.) This part will go a long way toward making your wearing of the glasses look DELIBERATE… not like you just threw them on because you didn’t have time to get ready (even if that’s true).

A NUDE LIP IS NEVER WRONG

Both Megan and Jennifer Aniston know this:

You might be used to wearing bolder lip shades (and you CAN wear them with glasses, but more on that in a sec). A simple nude or pink or peach lip gloss, however, is a no-brainer. Especially if you’re new to glasses, have glasses with a dark or heavy frame, and/or are not much of a makeup person. When you keep the lips subtle, they’re not going to fight with what’s going on up top. Easy peasy.

Oh, and do a gloss instead of a balm—when there is no colour, the pop of shine makes it look more dressy.

EMPHASIZE YOUR LASH LINE—NOT YOUR LIDS

And this brings me to the delightful Anne Hathaway, whose execution of my point here couldn’t be better:

So I already said that going all dramatic on the lids, in order to compensate for the eyewear, isn’t advisable.

Does that mean you shouldn’t wear ANY eye makeup? Hells no. What you want to do, instead, is to focus on the lash lines and lashes as much as humanly possible. So: do tons of black volumizing mascara on both the upper and lower lashes. (None of this brown business. Everyone looks good in black mascara.) Then, as Anne has done, line all the way around the eye with a brown or grey or navy pencil. (Not black though—too harsh.) I’d do the inner rims; see here for tips on waterproof liners that last. If you must wear shadow, stick to something really soft, like a beige or peach. (P.S. Speaking of peach, that peach blush and matte peach lip are outstanding!)

You can go a bit heavier with the eyes if you’re wearing glasses without frames, like Alicia Keys here:

Oh, and because some lenses can give you dark circles, make sure you follow my all-time favourite concealer tip for making your eyes look wide-awake and well-rested.

GO AHEAD AND DO A BRIGHT LIP

You can! Really. As long as your glasses are black or brown (not coloured). And make sure you do it with frames that are fairly substantial too, because they need the chunkiness to balance them out. Leona Lewis shows us how it’s done:

Notice how soft the eye makeup is? This is my favourite way to wear a bright lip anyway—with just mascara and the tiniest hint of eyeliner, basically—but it’s even more important with eyewear.

Chloë Sevigny goes for a classic red:

Again, all the elements are there: quirky, heavier frame (at least at the top part) plus a big lip, plus a minimal eye. I love those long eyelashes!

WEAR COLOURED SHADOW AT YOUR OWN RISK

Brights on the eyes can be risky with glasses or without—but if you’re gonna try it, please look to glasses superstar Alicia Keys (again) for inspiration:

Fun, right? There are a number of reasons why this works so well:
a) It’s focused just around the lash line.
b) It’s “grounded” with brown/black eyeliner.
c) The frames are black, chunky and modern, so they “match” (coloured frames would be disastrous!).
d) The lip is soft and glossy.
e) The rest of her outfit doesn’t introduce any other colours.

Now tell me:

Do you wear glasses?
How do you wear your makeup with ‘em? Do you find it a challenge?
Which celeb do you think rocks her glasses best?