In the summer of 2016, before she hit age 30, Lauren Friedman ’09 published her second book, 50 Ways to Wear Denim, which presents hand-drawn outfits with a denim motif. Tidbits about the history of denim accent pages filled with color-ful “how-to” drawings that offer ideas for wearing anything from bell-bottoms to jean jackets. Though no one who knows her is surprised by the career she’s carved for herself, her path to being a full-time artist and author was filled with what she affectionately calls “fits and starts.”

How did you land your first book deal?

After graduating from Wellesley as a political science major, I moved to D.C. and worked a series of regular 9-to-5 jobs. The best part of my day was getting dressed for work. I was fatigued from constantly looking at a computer screen, so I started an illustrated personal-style blog called My Closet in Sketches. I drew whenever I got home from work, creating outfits from my wardrobe and giving them names such as “Dead Poets on the Green” and “Drag Queen Brunch.” Within a year of starting the blog, I was able to become a full-time freelance artist. A friend encouraged me to write down my one-year, five-year, and 10-year goals. Under my one-year goals, I said I wanted to publish a book with Chronicle Books. A year later, during Hurricane Sandy, I was at a friend’s house watching nature documentaries and drinking wine, and I got an email from an editor at Chronicle Books who had seen a post about scarves from my blog and asked if I wanted to write a book for them. This became 50 Ways to Wear a Scarf. If there’s one ability I feel really confident about, it’s telling people what to wear!

How long did it take to create Denim?

When I was working on 50 Ways to Wear Denim, I would draw for 10 hours a day, pulling 60-hour weeks for almost two years. There was always a pile of clothes on my bed as I was constantly trying on clothes. (Most of the clothes illustrated in the book are my own, including items passed down from my mom and grandmother.) The same part of me that went to Wellesley is the part that enjoys working like this.

Tell us about your grandmother Enid and how she’s inspired you.

I have to admit I didn’t really get to know her until I started going through her closet after she was moved to an assisted-living facility. I found that even though she had lived a very traditional life as a housewife, she expressed her creativity through her clothes. I realized my blog’s tagline, “Always an excuse to dress up,” didn’t come from nowhere, it came from her. She passed away in 2015, and I try to wear something of hers every day.