Aviator sunglasses are like leather jackets. They make you look cool, but only if you're already cool enough to pull them off. I have a tough time with both—I feel like a stock photo of a hip baby. You can't wear a leather jacket unless you mean it, and you can't wear an aviator without conviction. Which brings us to today's topic.

About a year ago, a collaboration was struck up between two of the things I love most in the world: Into The Gloss (where I regularly flood your screen with posts) and Warby Parker (where I work every day, at a cute desk next to a potted tropical tree). “Let's do a collaboration!” I said to Emily and Nick. “Yes!” said Emily and Nick. There began the process of assembling inspiration, designing frames, producing technical drawings, prototyping, embossing lens cloths, tweaking packaging, and reviewing samples. (This is how your glasses are made, FYI.) The result: two pairs of beautiful frames. One pair of aviator sunglasses and one pair of optical frames, built to ITG's exacting specifications.

Why did we collaborate? First, for fun. Second, because history has taught us that combining two good things into one can have pleasing results—for example, toast with cinnamon AND sugar, or drinks with gin AND champagne or flags with stripes AND stars (USA! USA!).

In Emily’s case, the goal was to create the ideal pair of aviator sunglasses. This is not easy, but at least it's straightforward: the frame must be tear-droppy but not tear-droopy; the top bar must be proportionate with the bridge; the material should be titanium. The scale of the lenses should be appropriate, striking an Emmanuelle Alt vibe rather than an Unabomber police sketch vibe.

Nick brought a trickier idea to the table: he wanted to create the ideal pair of optical aviators. Specifically, a pair that was elegant and wearable—vintage-y without being costume-y. Something that would look great on both a cool old man AND an Olsen twin. Not, to address the elephant in the room, Terry Richardson or Dov Charney aviators. As design challenges go, this is the equivalent of a Saturday crossword puzzle. (“Ambitious,” we’ll call it.)

That’s the short story about why it took a whole year to produce these specimens. The longer story is that we spent a lot of time on the details, right down to the little insert card and custom pouch that comes with each pair. When the frames were finished and Emily and Nick each tried on their signature pair, there was almost an audible “click!”

As for me, well. I stopped by the ITG office to get Emily’s verdict on whether I could pull off the glasses or not. (She is very honest.)

I put on the sunglasses. Emily turned her head 25º to one side. “Zhush up your hair,” she said. “Fluff out your shirt a little. It looks uncomfortably tight where you’ve tucked it in.” I did both and stood against a wall, where Emily took pictures.

“Now put on the optical frames,” she directed.

“I’m afraid that I will look like a pervert in these glasses,” I admitted, putting them on.

“Then maybe don’t lick your lips like that while you’re wearing them,” Emily said. “Hold on, I’ll get you some lip balm.”

Snap snap snap. “These make your eyes look huge,” Emily said.

“Do I look creepy?”

“No. You look like a hot babysitter.”

A thrilled shiver traveled up my spine. A hot babysitter is exactly what I want to look like in summer: friendly but not fussy, with a face that says, “I am responsible for the welfare of small children,” and a booty that says, “I like long walks on the beach—and beer!”

Next stop: leather jackets.

—Molly Young

Molly Young photographed by Emily Weiss on June 22, 2014 in New York. Shop the collection here.