Jennifer Mason
Credit: Alex Reside for (2)

My natural hair color is a light, mousy brown. To add contrast, I began highlighting it in my teens, and by my mid-twenties (around the time I started going gray) I had so many highlights that I was essentially a blonde. Every colorist I worked with assured me that the hue was right for me because it looked natural, it blended in well as my roots grew in, and the upkeep was low-maintenance. That’s all well and good, but there was one problem: I was seriously bored with my hair color. Each day, on my commute to and from the InStyle office, I looked at the other train passengers and noticed that every other woman’s hair looked a lot like mine. I decided I was ready for a transformation and spoke to Gregorio Ruggeri, of New York’s Ruggeri Salon, about going brunette. He was enthusiastic about the idea—and we set out to choose a color that complemented my complexion.

If you’re thinking of making the leap, consider these tips Ruggeri gave me to make sure you’re ready to hit the bottle, too.

Scour the Internet
First, I searched for images of dark hair colors that I liked, and then narrowed the photos down to women with light eyes and light skin with olive undertones, just like me. I showed the pictures I’d found to Ruggeri, and we settled on the hair color of financial TV journalist Maria Bartiromo, circa 2006.

Experiment with Swatches
I was worried that I might look pasty or like I was wearing a brown wig. Gregorio brought out a selection of brown hair swatches and placed each one next to my face until we pinpointed a hue that brightened my complexion.

Go the Semi-Permanent Route
Ruggeri recommended that we test out the look by first using a semi-permanent color rather than permanent dye. That way, if I hated the way I looked with dark brown hair, it wouldn’t be as challenging to revert to blonde.

An hour and a half later, I was a multi-toned brunette. I love the color, and almost immediately, people began to compliment me on my blue eyes. A few even told me I looked younger. Next time I’ll definitely opt for the permanent formula.