On a trip through the history of Kourtney Kardashian’s hairstyles past, it’s clear that she’s anything but “the least interesting to look at” (to quote her sister, Kim, that is). The mom of four and wellness enthusiast definitely lives a more low-key life in comparison to the rest of her family, often ditching the traditional glam they love in favor of looks that are more laid back and effortless with a rock-and-roll twist — like short black nails and slicked bobs, for example.

But it hasn’t always been that way. When Keeping Up with the Kardashians first blew up in the mid-aughts, the Lemme founder was all about the perfectly coiffed hair and contoured makeup. That time produced some memorable beauty moments, too, but over the years she’s fully settled into her signature style. Sometimes that means something more simple, like a sleek low bun (one of the The Kardashians star’s staples), but when the mood strikes she’ll switch things up with high glam retro bouffants, long, wild waves, and bouncy half ponytails. While she’s carved out her own unique niche in the fam, the Poosh founder isn’t afraid to try new things, and it’s what makes her style journey through the years such an interesting (wink, wink) one. Ahead, see all the bobs, top knots, and more that made for her best hair looks to date.

Milkmaid Braids

At a March 20212 event, Kardashian opted for a whimsical braided hairstyle that’s both sweet and chic. To complete the beauty look, she added glossy pink lips, and classic red nails.

Sky-High Top Knot

So many women try to achieve that perfectly imperfect, effortless top knot that Kardashian has always done so well. The sky-high placement makes this one feel extra playful and perky.

Long Sleek Ponytail

The wellness lover has discussed dealing with traction alopecia as a result of ultra tight hairstyles, but it hasn’t stopped her from wearing them from time to time. But years ago, she was often spotted in pulled-back looks like this long, sleek ponytail from 2017.

Braided Baby Space Buns

A forever ‘90s baby, Kardashian showed her love for the throwback style with her two itty-bitty braided buns back in 2020.

Half-Up Holiday Ponytail

When the holiday season arrives, you can count on the Kardashians — including Kourtney — to pull out all the stops with their glam. For her Christmas 2020 festivities, she sported a bouncy half ponytail accessorized with a bedazzled headband.

Wild & Waist-Length

In 2021, Kardashian grew her natural hair all the way down to her waist, often wearing it with a little wave for a mermaid-like texture.

Low Baby Bun

Who says short hair can’t create updos? The minimalist style lover’s low baby bun gave her micro bob a little variety and paired perfectly with her red leather look.

Wet Bob

Kardashian has been a big proponent of the so-called hydro bob (a wet look bob achieved through gels, oils, and/or shine serum) starting in 2022. She’s worn the look on repeat ever since.

Bleached Blonde Bob

What would a rock star’s wife do? Bleach her hair on a whim, for one thing. That’s exactly what Mrs. Barker did in 2023, when she dyed her chin-length bob platinum blonde.

Retro Bouffant

Kardashian channeled ‘60s icons like Brigitte Bardot for a Lemme shoot in 2024. Her retro bouffant came courtesy of celebrity stylist Dimiris Giannetos, and it was a glamorous blast from the past.