Prepare to Be Inspired by Jenna Lyons's Powerful Essay on Confidence

Jenna Lyons has a fervent band of style fanatics following her every bold, fashion-forward look. The president of J.Crew is known for not being afraid to break basically every single fashion rule. But despite her current status as fashion darling, Jenna admitted in the most recent issue of Lenny Letter that things weren't always that way.

Jenna admits that her current job has three requirements. "1. That I have confidence. 2. That I spend time reviewing endless contact sheets of beautiful, perfect, glowing models. 3. That, to my absolute shock, surprise, and deepest appreciation, I am often talked about favorably for how I look. Beautiful, excited, and nervous young girls and even boys actually ask to take photos with me. They apologize for interrupting me."

Yet her current self-assurance was hard won. After struggling with depression and lack of confidence during her childhood, there's one thing that changed her life: she learned to sew.

"I got to go to Florence Fabrics, pick out a Butterick pattern and three yards of fabric, and make something that actually fit me — my measurements, my length, my custom-made watermelon skirt," Jenna wrote.

Jenna attributes that one vibrant skirt for helping to change everything. "It marked the beginning of my own private, self-initiated makeover. But it also marked the beginning of my understanding transformation. I realized for the first time that people's memories are short and their opinions are malleable."

Scroll for six outfits that prove Jenna is the fashion world's boldest style muse, and subscribe to Lenny Letter to check out the essay in full.