If there's one item that everyone needs to have in their wardrobe, it's a pair of jeans. Wide-leg or straight, light wash or deep indigo, denim has truly earned a place in every closet. And while today's influencers are always delivering plenty of outfit inspiration, it's a handful of truly iconic A-lister looks that stay fixed in my memory. Whether from the Nineties or just this past awards season, these are looks that I consider denim classics.
As these looks prove, gone are the days when jeans were only for casual daytime wear—although they'll always be my daily go-to. With a few easy styling tweaks, your denim can be dressed for any occasion. Just look at Julia Roberts wearing jeans and a blazer on the red carpet at the Venice Biennale. But if you do need a refresh of your daytime denim ensembles, look to the women who nail classic, effortless elegance, like Carolyn Bessette-Kennedy or Princess Diana.
Here, discover my edit of the truly iconic jeans outfits that stand the test of time, and the pieces you need to recreate the look for yourself.
The Most Iconic Jean Outfits:
1. Carolyn Bessette-Kennedy
Style Notes: With a new TV show focused on the romance between Carolyn Bessette-Kennedy and John F. Kennedy Jr. on the way, the American fashion icon has been on my mind, and what better outfit captures her style than this? Effortlessly chic, as was her signature, this combo of classic blue jeans and black pieces is a 10/10.
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A black polo is a wardrobe essential.
I'm such a fan of Reformation jeans.
Coat season is approaching, and this style is such a classic.
A great investment pair.
The ultimate Carolyn accessory.
2. Beyonce
Style Notes: Fresh off the Cowboy Carter tour, Beyonce has brought back Americana-inspired denim in a big way. If you're looking to embrace the double denim look this season, follow her cue and go for a Western-inspired combination complete with shag jacket—cowboy hat optional.
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A lightweight denim top is great for all seasons.
Such an easy, everyday fit.
So cool.
3. Alexa Chung
Style Notes: Alexa Chung has always nailed elevated-casual daytime wear, and this outfit is the perfect example. I love how she uses wardrobe staples like a blazer and Breton stripe top, but gives it a playful twist with the gold heels.
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An all season must-have.
Supremely elegant — a great way to smarten up blue jeans.
This light wash is so versatile.
Carrie Bradshaw would approve.
4. Laura Harrier
Style Notes: If anyone can prove that jeans are appropriate for nighttime, it's Laura Harrier. The impeccably dressed star nails the elegant jeans look by pairing a silky shirt and heels with her blue denim.
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This looks so much more expensive than it is.
I love the fit of Agolde jeans.
Timeless.
5. Princess Diana
Style Notes: Perhaps one of the most iconic jeans outfits is this look by Princess Diana, which cemented blue denim as a true fashion essential. This is a masterclass in layering.
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A preppy dream piece.
Ideal for those who like a slim fit.
Riding boots are making a big comeback this season.
Such an easy layering piece.
The ultimate finishing touch.
6. Cindy Crawford
Style Notes: My kind of airport outfit. This look is such a Nineties vibe—blue jeans, classic white shirt and layered blazer and knit.
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Every wardrobe needs a crisp white shirt.
Our editors swear by COS jeans.
Made for layering.
This ribbed texture makes it look so much more expensive.
Suede ballet flats are such an elegant way to elevate denim looks.
7. Sienna Miller
Style Notes: Think of Sienna Miller and you think of effortlessly cool style. This outfit perfectly captures that association—simple blue jeans given a subtly rocker lift with a leather trench and pointed-toe boots.
A close-fit top is brilliant for cold weather layering.
Obsessed.
A Nineties-inspired look calls for Nineties jeans.
How sleek?
8. Julia Roberts
Style Notes: In case you needed further proof that jeans can work for any occasion, Julia Roberts recently made an iconic red carpet move by wearing this denim ensemble to the Venice Biennale. I can't wait to copy.
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I love these earthy colours.
Dark blue denim is having a comeback this year.
The perfect oversized fit.
The patent heel is always so cool.
9. Hailey Bieber
Style Notes: If you're a baggy jeans fan, Hailey Bieber is likely on your inspiration board. She always nails the cool, undone look, and I love the way she mixes different styles here, pairing the rugby shirt with a leather bomber to create an undeniably cool outfit.
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The corduroy trim collar is such a cool touch.
For those who like a loose fit.
Hailey would definitely approve.
You could also swap for trainers.
10. Jennifer Aniston
Style Notes: Jennifer Aniston's late Nineties/early Noughties looks are always on my moodboard, and this outfit is top of my list for a understated evening look. A sheer shirt and cuffed jeans? Sign me up.
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This really looks like a designer find.
Style for day or night.
The goes-with-everything heel.
