Outfits
Jan 29, 2021

From Diana Ross to Jen An: These Are the 24 Best Denim Outfits Ever

by Elinor Block

Denim lovers, jeans aficionados and people who just really love a great pair of cutoffs, today is your lucky day. We've put together a list of really great, iconic in some cases, denim outfits. Before we get started, however, there's one point that's worth noting: we've mainly stuck to women's outfits. While there are a plethora of well-dressed men wearing jeans (Marlon Brando, James Dean et al), not enough space is dedicated to the coolest denim outfits as seen on women, and boy, have we found some doozies.

Over the past few decades, since jeans became a wardrobe staple for quite literally everyone in the world, there have been some incredible outfits as seen on the A-list. From '90s Jennifer Aniston in Friends to Diana Ross partying wearing a nice top and jeans, there are so many women whose looks we would still wear today. Right now, after years of skinny jeans obsession, we're going towards a baggier, looser fit trend. And while stretchier and more comfortable silhouettes could be attributed to the pandemic and our love of clothing with more give, it's clear that this '90s style of denim has been bubbling up for a while now. But there's also no denying that '70s flares are also still popular among plenty of the fashion crowd.

The only thing to do then is look back at all of the best denim looks that have come before. You'll not only get some outfit inspiration, you might even realise that maybe hanging on to that pair of classic straight-leg jeans wasn't such a bad idea after all, as the trend is bound to come back around again. Keep scrolling and dive straight into some denim nostalgia.

iconic denim looks: rachel green and ross gellar wearing blue jeans and a white top

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Style Notes: This might be a character's wardrobe, but Rachel Green made jeans and a plain tee look amazing.

iconic denim looks: britney wearing a denim dress in 2001

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Style Notes: The ultimate denim dress. Britney's frock (and matching look with Justin Timberlake) at the American Music Awards in 2001 goes down in the denim history books for sure.

iconic denim looks: princess diana wearing a pair of blue jeans with a blazer and white sweatshirt

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Style Notes: Has anyone worn blazers with jeans in such an iconic way since?

iconic denim looks: iman at the alaia show wearing a denim dress

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Style Notes Iman looking incredible in a denim dress on the Alaîa runway. Bonus points for spotting Andy Warhol on the FROW.

iconic denim looks: kate moss wearing skinny jeans, bella freud jumper and a mulberry bayswater

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Style Notes: Our queen of skinny jeans, Kate Moss, proved that all you needed in the mid '00s was a Bella Freud jumper and Mulberry Bayswater tote to look amazing.

iconic denim looks: sienna miller wearing jeans tucked into uggs with a white vest top

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Style Notes: More '00s goodness for you. This time it's one of Sienna Miller's classic jeans-tucked-in Uggs look. Forever to be repeated in every student union all over the UK for the rest of the decade.

iconic denim looks: beyonce wearing denim peddle pushers and a blazer

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Style Notes: Lest we forget the ubiquitousness of peddle pushers in the '00s. Here we see them in denim form, as worn by Beyoncé.

iconic denim looks: cindy crawford wearing jeans with a black leather jacket

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Style Notes: We'd absolutely wear this '90s Cindy Crawford look today.

iconic denim looks: Gwyneth paltrow wearing bootcut jeans and an hermes bag

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Style Notes: All hail the bootcut jeans that were in every woman's wardrobe in the early '00s. Miss Sixty was our preference, how about you?

iconic denim looks: salt-n-pepa wearing stonewash denim

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Style Notes: The '80s were all about stonewashed denim, and Salt-N-Pepa weren't immune to it, especially in looser, baggier styles.

iconic denim looks: jennifer aniston wearing straight leg jeans in the '90s

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Style Notes: Can you believe that this look is from 1998 and not today?

iconic denim looks: naomi campbell wearing a pair of blue bootcut jeans with a black cropped top

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Style Notes: Naomi always looks incredible but this outfit is *chef's kiss*.

iconic denim looks: jlo wearing white jeans, a bandana and a white crop top at the VMAs 2000

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Style Notes: Of all the J-Lo denim outfits we could choose from (and trust us, there were a lot), this wins. For the love of rhinestones we couldn't not pick this from the VMA awards in 2000.

iconic denim looks: alexa chung wearing a pair of denim shorts, striped top and a black leather jacket

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Style Notes: Another British denim icon is, of course, Alexa Chung. A denim aficionado, it was her dedication to cutoffs at various festivals that we've loved the most over the years.

iconic denim looks: TLC wearing baggy denim dungarees in the '90s

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Style Notes: If you owned a copy of Crazy Sexy Cool or at least knew all the words to "Waterfalls," then you get the obsession with TLC. Their style was super cool and baggy denim is a silhouette we're loving for spring/summer 2021.

iconic denim looks: the cast of the sisterhood of the travelling pants in 2005

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Style Notes: The stars of The Sisterhood of the Travelling Pants movie show us just how much we loved bootcut jeans and big turn-ups in 2005.

iconic denim looks: farah fawcett wearing blue flare jeans, a red jumper and nike cortez

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Style Notes: Flares, a red jumper and a pair of Nike Cortezs. What. An. Outfit. Farah Fawcett is such a vibe.

iconic denim looks: thelma and louise wearing jeans and cut-off shirts

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Style Notes: Cutoff tees and high-waisted blue denim is arguably one of the greatest looks of all time, even if this is from Thelma and Louise. And I won't hear another word on the matter.

iconic denim looks: jane birkin wearing blue jeans and a white top

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Style Notes: At some point, we all realise that Jane Birkin looked incredible in jeans and that she's how we all aspire to look in ours too.

iconic denim looks: marilyn monroe in a pair of blue jeans and a white shirt

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Style Notes: Marilyn Monroe might have been known for more high-octane outfits, but she looked just as fabulous in a white button-down and a pair of classic blue jeans.

iconic denim looks: cher wearing blue jeans and a vest top

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Style Notes: Is it the cute cami top tucked into the high-waisted flared jeans, or is it that it's Cher and everything she does is fabulous? Either way, this remains an iconic denim look from the '70s that we continue to love.