I Let My Hairstylist "Surprise Me" — and Ended Up With the Haircut of My Dreams

It's hard to tell without Enola Holmes's magnifying glass just how frayed my ends are here, but I'll put it this way: my split ends had split ends. I needed to cut off a lot of length . . . and STAT.

Luckily, Sherman knew exactly what to do. Without taking a beat, and after hearing my three choices, he was ready to go all in on the shaggy lob haircut, but with a few modern twists on the throwback style.

"With your face shape, you want a cut that takes the focus from the cheekbones up," he told me, adding that shaggy, face-framing pieces can help achieve that effect. This, he explained, is different from doing so with all-over layers: "Your hair has built-in texture, so we don't want to do too many layers. We'll just keep it one length at your clavicle."