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
(Image credit: Getty Images)
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.
Shop the look:
Whistles
Black Essential Ribbed Polo
A black polo is a wardrobe essential.
Reformation
Cynthia High Rise Straight Jeans
I’m such a fan of Reformation jeans.
COS
Belted Double-Faced Wool Coat
Coat season is approaching, and this style is such a classic.
The ultimate Carolyn accessory.
2. Beyonce
(Image credit: Getty Images)
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.
Shop the look:
Levi’s
Teodora Lightweight Western Shirt
A lightweight denim top is great for all seasons.
Such an easy, everyday fit.
New Look
Brown Faux Fur Coat
3. Alexa Chung
(Image credit: Alamy)
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.
Shop the look:
M&S Collection
Pure Cotton Striped Slash Neck Slim Fit Top
Weekend Max Mara
Weekend Max Mara Virgin Wool Blazer
Supremely elegant — a great way to smarten up blue jeans.
Toteme
Classic Cut Denim Worn Blue
This light wash is so versatile.
Carrie Bradshaw would approve.
4. Laura Harrier
(Image credit: Getty Images)
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.
Shop the look:
Autograph
Pure Silk Collared Button Through Blouse
This looks so much more expensive than it is.
AGOLDE
Kiera Mid-Rise Wide-Leg Organic Jeans
I love the fit of Agolde jeans.
5. Princess Diana
(Image credit: Getty Images)
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.
Shop the look:
Polo Ralph Lauren
Embroidered Crest Fleece Crewneck
FRAME
The Ruler High-Rise Slim-Leg Jeans
Ideal for those who like a slim fit.
Reformation
Nancy Knee Boot
Riding boots are making a big comeback this season.
hush
Jayde Italian Wool Blazer
Such an easy layering piece.
The ultimate finishing touch.
6. Cindy Crawford
(Image credit: Getty Images)
Style Notes: My kind of airport outfit. This look is such a Nineties vibe—blue jeans, classic white shirt and layered blazer and knit.
Shop the look:
With Nothing Underneath
The Boyfriend Exaggerated Cuff: Fine Poplin, White
Every wardrobe needs a crisp white shirt.
Our editors swear by COS jeans.
Nobodys Child
Black Double Breasted Blazer
Whistles
Neutral Aria Wool Mix Crew Knit
This ribbed texture makes it look so much more expensive.
GABRIELA HEARST
Fleur Suede Ballet Flats
Suede ballet flats are such an elegant way to elevate denim looks.
7. Sienna Miller
(Image credit: Getty Images)
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.
M&S Collection
Second Skin Long Sleeve Top
A close-fit top is brilliant for cold weather layering.
NOUR HAMMOUR
Kasha Belted Leather Trench Coat
AGOLDE
90’s Pinch Waist Long Frayed High-Rise Straight-Leg Jeans
A Nineties-inspired look calls for Nineties jeans.
M&S Collection
Leather Kitten Heel Pointed Ankle Boots
8. Julia Roberts
(Image credit: Getty Images)
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.
Shop the look:
ZARA
Striped Shirt With Back Tab
I love these earthy colours.
Gap
Dark Blue High Waisted ’90s Loose Jeans
Dark blue denim is having a comeback this year.
H&M
Textured-Weave Blazer
The perfect oversized fit.
Reformation
Joelle Heeled Pump
The patent heel is always so cool.
9. Hailey Bieber
(Image credit: Getty Images)
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.
Shop the look:
WALES BONNER
Reflect Corduroy-Trimmed Striped Cotton-Blend Polo Shirt
The corduroy trim collar is such a cool touch.
ALIGNE
Low Rise Loose Wide-Leg Jeans
For those who like a loose fit.
The Frankie Shop
Viper Leather Jacket
Hailey would definitely approve.
MANGO
Kitten-Heel Pointed-Toe Ankle Boots
You could also swap for trainers.
10. Jennifer Aniston
(Image credit: Getty Images)
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.
Shop the look:
French Connection
Arezzo Neck Tie Shirt
This really looks like a designer find.
MANGO
Wide-Leg Jeans With Turn-Up Hem – Women
The goes-with-everything heel.
