It’s UGG Season! A Celeb History of the Divisive but Oh-so Comfy Boot 

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It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonKylie and Kendall Jenner in 2008 Getty Images

There’s a lot to love about September: you can treat yourself to a cute new pencil case (whether you’re 8 or 38), stop feeling like you have to fake tan and relax into your fall/winter wardrobe.

But the big question is, does your fall/winter wardrobe involve the most controversial footwear of the 21st century: the UGG boot?

If you’re Kendall Jenner, Emily Ratajkowki or Hailey Bieber, the answer is likely to be a resounding yes: all three fashion-forward stars have rocked the boots in recent years, from the ankle version to platforms to the mid-calf originals. For everyone else? It’s a tough decision.

The infamous style of boot that we now know as UGG was first worn by sheep shearers in Australia and New Zealand in the 1920s, but was transformed into a brand for surfers in California in 1978. It wasn’t until the early 2000s, though, that UGG became a mainstream fashion brand, with stars like Paris Hilton and Britney Spears rarely wearing anything else during off-duty outings — and sometimes even on the red carpet.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonHailey Baldwin in 2016 Getty Images

The thought process for every UGG wearer goes a little like this: Eww, I wouldn’t be seen dead in those ugly things. Hmm, I’ll just try them on in the store for fun, to see how ridiculous they look. Ohhhhhh, these things are comfy, maybe I’ll get some just for wearing around the house? OK, I’m just heading out for milk, I won’t see anyone so there’s no point in changing into real shoes. Wow, that wasn’t so bad, maybe they’re OK for every day after all. Oh, the Kates (Moss and Middleton) wear these things? I guess they must be acceptable after all.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonKate Middleton in 2007 Mel Bouzad/FilmMagic

Beware: it’s a slippery slope, and before you know it, you’ll be wearing them under your wedding dress. So, let’s take a look at the celeb history of UGGs to help you decide whether you’ll succumb this season …

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonKimberly Stewart Donato Sardella/WireImage

Could there be anything more 2003 than these words: Kimberley Stewart, pink velour, classic UGG boots?

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonParis Hilton and Nicole Richie Dimitrios Kambouris/WireImage

Yes, actually, there could: Paris Hilton, Nicole Richie, Motorola flip-phone launch, low-rise Juicy Couture sweatpants and fur-trimmed UGG boots. A work of modern art for sure.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonBlake Lively and Sam Page Marcel Thomas/FilmMagic

The UGG has remained a popular on-set choice for stars on their feet all day, safe in the knowledge that their shoes wouldn’t make the final edit, from Blake Lively on the Gossip Girl set back in 2010, making an on-set smooch with Sam Page more comfortable, to Chrissy Teigen getting shoot-ready earlier this year.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonChrissy Teigen Bellocqimages/Bauer-Griffin/GC Images
It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonNicole Kidman Jose Perez/Bauer-Griffin/GC Images

A shoe for all seasons, as Nicole Kidman found out early in 2024, UGGs don’t look great in the rain, but they do keep your feet cozy — and the UGG with opaque tight combo is a cold weather commuter classic, as demonstrated by Sienna Miller in 2007.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonSienna Miller Mel Bouzad/FilmMagic

UGGs on the red carpet are a controversial choice, but one that these stars threw themselves into enthusiastically, with extra points for choosing an embellished UGG or one in a vibrant shade of ‘00s.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonBeyonce in 2004 Frank Micelotta/Getty Images
It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonJoss Stone in 2005 Chris Polk/FilmMagic

The ‘00s Trends Stars Like Meghan, J-Lo and Rihanna Are Embracing

What a bizarre time: celebrities were either wearing eight-inch bejeweled Louboutins or sheep-shearer boots with very little in-between (apart from ballet flats, another controversial ‘00s shoe on the comeback trail, ready to take you down one sore arch at a time.)

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonPharrell Williams in 2014 Gilbert Carrasquillo/FilmMagic

And men can UGG too! Pharrell Williams is a long-term fan.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonCameron Diaz in 2003 Bauer-Griffin

But the classic UGG wearer is usually female and off-duty; whether walking the dog, shopping, grabbing coffee or trudging through the airport, they are usually found smiling smugly about how comfortable they are.

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonKendall Jenner in 2023 Bellocqimages/Bauer-Griffin/GC Images
It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonJessica Simpson in 2011 Alo Ceballos/FilmMagic
It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonJennifer Lopez in 2024 Ignat/Bauer-Griffin/GC Images

Are the new styles, like Jennifer Lopez’s platform version and Emily Ratajowski’s ankle-grazers, more aesthetically-pleasing, or have we just got used to them?

It’s UGG Season! A History of the Controversial Boot via Kendall Jenner, Jennifer Lopez and Paris HiltonEmily Ratajkowski in 2020 Jose Perez/Bauer-Griffin/GC Images

Us wonders, in a shallow world, have we found the ultimate proof that it really is what’s on the inside that counts? In the case of UGGs, that’s sheepskin, and very cozy feet.

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