Jennifer Aniston’s Best Haircuts, From 1990 To Now

Jennifer Aniston has had many memorable haircuts, but the most iconic of all depends on who you ask — and whether or not they've seen all ten seasons of Friends. The answer could be the full, heavily-layered shag known as the "The Rachel," or Aniston's early-2000s classic: a centre-parted, highlighted mid-length cut with gradual layers and a certain soft, effortless je ne sais quoi.

Following that viral Pitt-Aniston arm grab at the SAGs, this weekend's Oscars (the official end to 2020 award season) felt like an appropriate time to flash back to Aniston's best hair looks ever. From her dark brunette beginnings to the choppy lob immortalised in a sitcom, scroll through the gallery ahead for every Jennifer Aniston haircut that will undoubtedly inspire salon appointments for years to come.

Photo: Barry King/Liaison/Getty Images.

1990: Long & Dark

In the years before Aniston was cast on Friends, she was a 21-year-old Hollywood baby with long, fluffy hair a few shades darker than her now-signature honey blonde.
Photo: Reisig & Taylor/NBCU Photo Bank/NBCUniversal/Getty Images.

1994: Air-Dried Tousle

The first season of Friends featured a young Aniston with a shorter cut and tousled, air-dried waves (possibly from her splash in the fountain during the show's opening credits).
Photo: Kevin Mazur/WireImage.

1995: "The Rachel"

Who could ever forget "The Rachel"? Aniston's longtime hairstylist Chris McMillan gave the actress this short, choppy cut early in her career — and, like the sitcom, it came to define the '90s.
Photo: Allocca/DMI/The LIFE Picture Collection/Getty Images.

1998: Glossy Curls

This 1998 look invokes a foolproof beauty trio: shine oil, a curling wand, and, of course, lip gloss.
Photo: Steve Granitz/WireImage.

2001: Blunt Bob

Aniston married Brad Pitt in 2000, and chopped her hair into this blunt, polished newlywed bob shortly after.
Photo: Sean Gallup/Getty Images.

2006: Face-Framing Layers

Serendipitously, Aniston's divorce from Pitt coincided with the premiere of The Breakup — which she starred in alongside then-boyfriend Vince Vaughn — and debuting what's arguably her most coveted haircut to date.
Photo: Jason Merritt/Getty Images.

2009: Braided Accent

If Aniston's hairstyles have one thing in common, it's simplicity. This mini French braid accent is a chic, subtly romantic accent to an otherwise low-key look.
Photo: Kevin Winter/Getty Images.

2010: Side Fringe, 2010

In 2010, we were all wearing a side fringe — Aniston included. If we're being honest, though, hers might've been better executed...
Photo: James Devaney/WireImage.

2011: Zig-Zag Part

Aniston's slightly askew hair part is the perfect complement to her beachy blonde highlights.
Photo: Jonathan Leibson/Getty Images.

2016: Natural Roots

Aniston and her colourist, Justin Anderson, leaned into a more natural, grown-out root, blending to a lighter tone through the mid-shaft and ends.
Photo: Kevin Mazur/Getty Images.

2020: Soft & Pulled Back

In Aniston's most recent appearance at the SAG Awards, she paired her vintage Dior white silk gown with pared-down glam: barely-there makeup and hair down, tucked back behind her shoulders.
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