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 [1], 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 [2], and subscribe to Lenny Letter to check out the essay in full [3].

Mixed Sparkle

A Side of Fringe

Pajama Chic

White Out

Color Clashing

Suited Up