Age-Wise Style: My Life in Sunglasses

InStyle’s Fashion Director Cindy Weber Cleary has been a fashion editor for the past 20+ years. Needless to say, she's picked up some tricks along the way. Catch her column here each week for how-to tips and style secrets on her favorite, timeless styles.

For some, you can mark your years and memories with a specific hairdo or memorable scent. But for me, it was always about accessories and specifically frames that always lent an extra touch of air, chic and mystery.

The first pair of sunglasses I ever bought was the classic Ray-Ban aviator. That was in the '70s and I knew they made me look cool. I loved them and thought I would wear them forever! They flattered the shape of my face, and they went with everything from tattered jeans to my favorite Indian print sundress. I was loyal for a few years, but by the '80s, I had fallen for another Ray-Ban style -- the Wayfarer—and fell hard.

Forget about Tom Cruise in Risky Business. It was musicians like Madonna, Elvis Costello, Debbie Harry and Patti Smith who tugged at my heartstrings. The Wayfarers retro ‘50s vibe conferred instant rock and roll edge and that’s exactly the mood I was looking for when I moved to New York and started frequenting nightclubs like Danceteria and the Peppermint Lounge. Besides, they were the perfect complement to my black skinny Stephan Sprouse pantsuit.

Eventually, I ditched my bartender boyfriend back in the East Village. I was married and a mother. It was time to move on to an oversize frame with a dark opaque lens--very grown-up and glamorous. Suddenly the label on my temples seemed as important as the one my bag. Mine had double-C’s.

I stuck with an oversize frame for many years thereafter, but flirted with one luxury brand after another. That is, until designer shades became so ubiquitous that it almost seemed a brash faux pas to wear a recognizable pair. So when I came across a bold cobalt-blue frame with a slender metal temple from a designer I had never heard of, Thierry Lasry, I was seduced again. (It was called the “Sexxy” but I swear the name had nothing to do it!). I thought I had found my signature style and wore them constantly. It seems not one but two of my fellow fashion editors felt the same way: they wore the exact style during Fashion Week. The three of us walking around wearing big blue sunglasses in the same crowd looked ridiculous. Total buzz-kill.

So I vowed to keep it simple and just find the style that looks best on my face. When I tried to return to my first love, the aviator, I discovered that it’s magical powers had vanished. The downward slant of the lenses which had been so flattering in my youth now just emphasized the downward slant of my eyes and jawline. Sigh.

My search took an unexpected turn when I went on an appointment to see Norma Kamali’s last Spring collection. After showing me her designer line, she walked me through her very affordable KamaliKulture line to which she had recently added eyewear. Norma loves cateyes, so I decided to try on the style she calls “Square Cat” ($98, kamalikulture.com) and—bingo!—I found my new frames. This modified cateye is nothing like the kitschy ones your grandma wore in the '50s. These have a bold, almost sculptural upward sweep. Instant “facelift”!

True love at last…

Click through the gallery to shop the hottest, runway-inspired cateye sunglasses of the season!