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Before My Shaggy Bob Haircut

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."

Image Source: POPSUGAR Photography / Kelsey Castañon