Graduating from that awkward stage

Really successful people, to quote a pretty obscure Rihanna track, “shine bright like a diamond.” But diamonds, before emerging from Cartier on an Art Deco platinum setting, must undergo a process involving extreme pressure, transforming it from a hunk of carbon to glittering jewelry.

For many, that process is called high school. Many of today’s most successful didn’t peak in high school — that applies to almost everyone with a résumé worth reading, except maybe Gwyneth Paltrow. (Girl was popular on campus and was probably already well coiffed even as a zygote).

Like Claire Danes on My So-Called Life or Linda Cardellini on Freaks and Geeks, often the most interesting grown-ups had to go through an awkward stage before blooming into the kind of red-carpet bold-faced names they are today.

While flipping through old albums (those are printed photos, in case young people reading this don’t recognize images outside of a Facebook album) at my mom’s house, I spent most of the time squinting, cringing and sometimes crying out “What the f*&k was I thinking?”

Clearly, I thought plaid tennis shoes, cutoffs embellished with flowers in denim, and an oversized crew neck tee with a collar high enough to choke me were the best things since Walkmans and laser discs (oh, the ’90s). High school wasn’t any better, with oversized tees and flared denim. In college, I was obsessed with stripes — from preppy tees to the Adidas three-stripe. Paired with long khaki skirts, I was about as fashion forward as the Amish.

When one of the first gossip blogs emerged online, an anonymous troll snarked that I had no right being in fashion when I spent most of college in T-shirts that looked like something straight out of a Gap. To which I reply: au contraire, mon frčre. Those shirts were Gap outlet. Ha!

Growing out of a prolonged stage of awkwardness is tricky. It involves growth and maturity and the ability to laugh things off.

I polled a few of YStyle’s favorite talented people on growing out of their awkwardness. While the responses were varied, one truth emerged: it gets bad before it gets better. And by bad, I mean entertaining. There’s nothing like a badly-styled origin photo to humble even the most prosperous.

Lesley Mobo Designer

“I was not really interested in facts while at school — that’s my excuse for almost failing high school. Maybe the facts weren’t put in a way I found interesting, or it probably means my imagination hadn’t been fired up by academic tuition. 

“I’m at my lowest in that high school graduation picture with my mother, who was trying to make me smile after graduation. It’s the perfect awkward picture moment. After a month or so, I came up with a solution for the future: I decided I would rebel against bad briefs. This was my first step toward becoming a better person.”

Louis Claparols Designer

“I went through a lot of awkward stages through the years, especially during college when I was considered overweight. I was 200 pounds back then. Being a big Madonna fan — who we all know is a workout fanatic — turned me into one too, which gave me this goal to stay fit even when I turn 50, just like Madonna.”

Martin Bautista Designer

“When I started out, I was skinny and tended to wear clothes that were random, trendy, uncomfortable. I was finding my own vision, experimenting and looking for the right direction. Now that I’ve grown, I’ve developed a more classic, sensible and mature style which reflects my own aesthetic as a designer.”

Olivier Yoan Photographer

“At 17, I was just dumped by the first guy I truly loved, was hanging out in gay clubs, trying to be somebody people would love and it wasn’t working. Left high school a few days after that.

“Now, at 25 years old, after living in 13 countries and working as a photographer, I realized that the more I was myself, the more I was accepted and respected. Now I’m creating my own happiness.”

JC Buendia Designer

“Back when I was scrawny and had a cowlick, my claim to fame was being my cousins’ favorite escort. Top of the World was my theme song when I was hailed presidential designer, at my fittest, attending hip-hop class thrice a week!”