How Can I Feel More Comfortable Wearing Glasses?

"Guess what I got?" I goaded my boyfriend over the phone. By "boyfriend" I mean that we met at the mall one day, exchanged phone numbers, and decided over the phone to be boyfriend-girlfriend, and I saw him a total of three times in my life before "breaking up." I was, as you may have guessed, 13. "It's something that will make me look better."

"A new dress?" No. "New shoes?" No. "A new Trapper Keeper?"* (A new Trapper Keeper?!)

It was contact lenses, and his guesses were increasingly exasperating, because I took my contact lenses very, very seriously. Getting contact lenses was one of the best things that had happened to me in my 13 years on planet Earth. It also happened to coincide with slimming down a bit, gaining a couple of vertical inches, growing out my perm so it lost a bit of its ziggurat-like quality, and wearing the clothes I'd purchased on a family trip to the east coast, where I went shopping in Boston—at Filene's Basement even (which I'd even read about in teen magazines!)—instead of ShopKo. I was hardly a swan, but my contact lenses were essential to scooping me out of Awkwardland and landing me at least on neutral territory.

I never looked back. I keep a pair of glasses that I wear around the house, but in public, I am glasses-free—always. For a while it was the fear of seeming geeky (again, 13!), and I also connected shedding my glasses with suddenly entering an era in which I was, on occasion, considered pretty. Boys came a-knockin'—not that, Trapper Keeper guy aside, they would have knocked any earlier if I'd had 20/20 vision—and it all sort of got bundled up together. I always hated the boys don't make passes at girls who wear glasses quip (apologies, Dorothy!), and besides, I could witness at school that it wasn't true. Still, the idea stuck. I'm about as likely to wear my glasses to work as I am to come in with a chihuahua.

That would be the end of the story, if it weren't for my increased ocular discomfort. A combination of allergies (dust!), my profession (lots of screen time), and my environment (dirty, sweaty New York) means that about one out of four days, I'm in some pretty severe discomfort. (And let's not forget about how easily my eyes now get bloodshot, detracting from my otherwise glorious visage. Science says!) Going without my contact lenses is not an option (I'm at around 20/400, which Wikipedia tells me is legally blind but which I think just makes me a prime candidate to star in a hilarious rom-com, don't you think?). Which means: I've gotta learn how to wear glasses, preferably soon.

I see women every day who wear glasses and look smashing in them, either because they've chosen frames that mesh perfectly with their face to the point where you don't think of them as being a glasses-wearer but just the owner of a great face—or because they've chosen frames so distinctive that they jump out and become a statement. I don't look at any of my bespectacled friends and think, She'd be so pretty, if only... If anything, the women I know who wear glasses seem to project an air of efficiency and confidence, if only because I'm silently in awe that they feel comfortable doing something that makes me feel so self-conscious.

My level of enthusiasm for my glasses really can't be captured digitally.
Also note the spectacular failure of the fishtail braid. You're not here for my how-to advice, I gather.

One of my close friends, of the distinctive-frames sort, posits that my hesitancy comes from the fact that my glasses are, well, mousy. They're glasses that are trying to pretend like they don't actually exist, like they're just some odd arrangement of my hair that happens to resemble glasses. She's egging me on for spectacle-spectacles, and I want to try it, so I walk into store after store and try on frame after frame, and every time, I look in the mirror and hate what I see. I don't normally hate what I see in the mirror, mind you—it's something about having this thing on my face that catapults me right back to seventh grade, pre-contacts, pre-boys, pre-blossoming.

So, readers, I turn to you. I could really use some perspective on this: As a matter of my health and comfort, I seriously need to find a pair of glasses that I feel somewhat comfortable in. I need some wisdom to help me both find glasses that I like, and then to help me get over my self-consciousness once I'm wearing them. I long for the nonchalance that my glasses-wearing friends seem to possess—and more than that, I long for the comfort of not having my eyes twitch out more days than not.

Do you wear glasses? If so, how did you learn to be comfortable in them—or, if you always felt at ease in them, why do you think that is? Do you have tips on what to look for in a pair?

*This, as history would have it, was prescient. The era of Facebook has shown me that my ersatz boyfriend of 1989 now runs a delightful scrapbooking site with his partner, Donny. No wonder he thought a Trapper Keeper might up my appeal.