Dress Code: Everything You Ever Wanted To Know About Glasses But Were Afraid To Ask

Okay, maybe not everything. But in this Dress Code, we’re going to tackle the sartorial and practical issue nearest and dearest to my near-sighted, astygmatic heart: what’s euphemistically known as “face-furniture”:

I wear glasses all the time. I can’t do contacts and am not a candidate for laser surgery, so I long ago resigned myself to the joys of everyday spex. I have, at this time, about 6 functional pairs, 2 of which are prescription sunglasses. So this is not an issue I approach lightly. Now, many of you only wear glasses sometimes. Others, merely when it’s sunny. For a few, they’re a non-prescription fashion choice. I hope the following will help one and all.

On The Face-Shape Question: There are a lot of formulas out there for contrasting face-shape with frame shape. I, personally, think there’s no substitute for trying on a ton of pairs and seeing what works. That said, I’d feel remiss if this discussion did not at least include the accepted wisdom on the subject, so here, without further ado, is the traditional breakdown – which, if you’re feeling overwhelmed, might just help you narrow things down a bit.
If your face is round, the trad view is to go for a frame that’s angular and narrow, longer than it is wide.
If your face is oval, the recommended shape is as wide or wide than the widest part of your face.
For a square face, round or oval frames are recommended, as are thin frames.
Heart-shaped faces allegedly require frames that are wider at the bottom than at the top. (I guess this is what I should be doing.)
And a “diamond-shaped face” does well with geometric or oval shapes.
If you want more ideas, including what to avoid, here is a comprehensive breakdown.
Now, DISREGARD ALL OF THE ABOVE. It’s not that what these formulas recommend is unflattering, but it’s all based on the idea of “minimizing flaws,” which is never, to my mind, the way to approach any kind of visual shopping. Okay, don’t disregard it so much as take it with a grain of salt. Formulas may, again, be very helpful in narrowing down what can be a daunting field of choices, but theory should always come second to reality, and with glasses, more than anything else, there is no substitute for trying on shape after shape after shape.
It would seem, in fact, that I personally break all the rules for my face-shape. For a strong prescription with a high discrepancy between lenses, one is recommended to wear small frames. One is also told that, if one has a small or large face, to wear similarly-scaled frames. I don’t care and I feel like myself in big specs, and that, as they say, is that. (If you feel more comfortable doing something else that is, of course, your choice too.) You will wear glasses almost more than you do any single piece of clothing or accessory, and it needs to be something you can live with. That said, these things are non-negotioable.
Update Your Prescription: Whether at regular visits to you optometrist or the person at your local frames shop, keep it up to date. It’ll save you (literal) headaches and keep you from missing flights.
Make Sure They’re Comfy: Any eye doctor or glasses fitter should be able to tighten, loosen or adjust your frames according to your face shape and ear placement. You should leave the store with your frames feeling snug and secure but never painful, and as they loosen up, get them tightened or do it yourself with one of those maddening little kits you can buy in any drugstore.
Have A Backup: If you’re a regular wearer, this is crucial. Not only is it nice to have a backup if you roll/drop or crush your glasses, but it’s a well-known catch-22 of the poorly-sighted that when we don’t wear our glasses, we can’t find our glasses. Thus, a backup pair in a secure and easily accessible location is a decided boon.
When You Shop For Glasses, Wear Your Contacts. Because otherwise, you can’t see how things look. If you’re like me and you don’t wear contacts, bring a second opinion you trust with your life. This also adds an element of suspense to the whole proceeding! If you’re at a flea market and the glasses have old prescriptions in them, there’s really nothing you can do, sadly. Just don’t spend more than $20 in this case.

Try On Lots Of Pairs. I can’t say this enough. I went into glasses shopping with preconceived notions about what I wanted, all of which looked wrong on my face. It’s not that I object to looking ridiculous, but there’s deliberately goofy and then there’s “person with random glasses on face,” which is a common problem in advertisements showcasing “hot librarians” and “sexy secretaries.” To say nothing of American Apparel ads. You will know when a pair works, and when it doesn’t.
Consider Color. The color of the frames is important. Black frames may be cool, but they can easily wear your face like a pair of Groucho-nosed novelty specs. I for one do better with tortoise-shell or pink lucite, but we’re all made differently. Look how great these brown ones look on Johanna, who sells vintage frames on Etsy!

On Where to Shop. There are a lot of options out there and even the most mass-market has a lot of good choices nowadays. Designer frames can be expensive, but as with wedding-dress shopping, are worth trying: once you get a sense of what shape works, you can try to find a cheaper equivalent – or you may find it’s worth the expense to you.

On The Vintage Question: I only wear old frames, both because I happen to like the styles and because they tend to be tougher and cheaper. I get them at flea markets (beware the forementioned old-lenses question) and at Fabulous Fanny’s here in New York. I’ve found some very good 70s ones at thrift stores, too. I recommend taking any pair you buy to the optometrist to be properly fitted.

On The Online Question. I know a lot of folks who get their frames online, especially on eBay. It’s cheap and there’s a wide variety and, if you’re absolutely sure of what works for you, it seems like a great option. Personally, I am too scared, but I have heard plenty of success stories – and, again, often online things are cheap enough that the risk is small. Try searching “vintage women’s frames” or “tortoise-shell”, “cat-eye” “70s lucite,” “vintage plastic” – depending on what you like. This is a great site, too.

Troubleshooting:
On Pince-nez, lorgnettes, monacles: You know what, if you’re that guy, go for it. There is something strangely appealing about peering out a quizzing-glass like some intimidating character in a Georgette Heyer novel. Although I don’t see how practical this would be if you really have vision problems.
On Kissing. I personally find it very romantic when someone – either tenderly or determinedly – removes one’s glasses for a kiss. But there’s nothing wrong with taking them off yourself. Or, for that matter, just kissing in specs. Nothing bad happens as long as it’s just one of you. And if you both wear them, you’ll both have been plotting so it’s less of an issue.

On 3-D movies. Yes, it’s an issue. I’d say, if the contacts option is not open to you, to bring a couple of elastics or twist-ties to assist you in dealing with this cursed, deeply unfair medium.
On Athletics: I am very eager for sports-goggles – or even prescription shop goggles – to become cool. Until then, I’ve found my snuggest specs – and you can affix a discreet bit of elastic if needed – work. I am also a big fan of the school-marmish glasses chain, which one can easily find at any drugstore, looks pleasantly goofy, and is genuinely practical when doing anything that might occasion falling off.
On Pairing with Clothes: Yes, specs are something to take into account when self-styling, especially if you wear assertive ones. Keep in mind that you already have a lot going on and may want to go easy on statement earrings or hair accessories. On the other hand, they can immediately add a little edge to an otherwise sweet or more convetnional look. Here, one of our favorite stylistas (and sometimes spec-wearers) Definathalie, uses assertive glasses as an accessory:

On Hair: If you wear glasses regularly, take this into account with both haircut and color. Especially with bangs – although bangs and glasses (as modeled by Londoner Lucy on the Street Style blog PimPumPam, can look awfully neat.

On Costumes: This is perhaps where glasses are the biggest drawback. For the past decade, I have had to plan my Halloween costumes around specs, and really, you can only be Gloria Steinem so many times. That said, you’re generally the only one doing Bella Abzug, Linda Pugach, Sexy American Gothic, or Norma Desmond.

On Men Making Passes: I must say, I’ve noticed that the same few geriatric creeps and pre-teen nerds who hit on me before I wore glasses regularly haven’t seemed noticeably put off by their advent. Of course, before then (when I was 20), I stomped around in enormous 1940s housedresses all the time and/or was prepubescent, so it’s very hard to say. Anyone who’s got the control of going with and without, please do let us know your findings. This I do know: I wouldn’t want to be hit on by someone who wasn’t into glasses anyway. So there! (By the same token, “those are big glasses” is a lame opener.)