Cindy Crawford's black leather jacket, flared jeans and heeled boot outfit is one we're eager to recreate for the transitional months ahead
This combination is perfect for the cooler months around the corner


Cindy Crawford's flared denim jeans, black leather jacket, and heeled boots combination offers a masterclass in transitional styling—this look also shows us that some things never go out of fashion.
Striking the perfect balance between casual and elegant is not always easy; however, you can't go wrong with classic combinations such as denim and leather. And this daytime look from Cindy Crawford proves that some styles never go out of fashion—including biker jackets—watch as we eagerly add this style to our summer capsule wardrobes.
This outfit emulates everything we loved about Crawford's iconic 90s appearances, including those featured onscreen back in the day. She combines a classic black leather jacket, denim flared jeans, and heeled black leather boots as she strolls down the streets of Manhattan, New York.
Shop Cindy Crawford's Look
If you're looking for a leather jacket, this faux option from Zara is both affordable and very chic. Style with denim or layer on top of a white jeans outfit for a fashionable daytime look.
These blue jeans are made from breathable cotton, perfect for the warmer months. Dress up with heeled leather boots, or style with your best white trainers.
And although we're experiencing a bout of hot weather, the autumn months are right around the corner. And this transitional look is a practical styling combination that will see you through the upcoming months. By mixing and matching denim flares, a leather jacket, and heeled boots with other pieces in your wardrobe, you can create endless outfits suitable for all weather scenarios. Plus if you're on the hunt for summer work outfits then these are the staples you need.
Our woman&home Digital Fashion Editor Caroline Parr comments on this look, "Cindy Crawford is the queen of classic ensembles (something she's passed on to daughter Kaia), and it doesn't get any more timeless than blue jeans, black boots, and a leather biker jacket."
Later saying, "This will be a failsafe trio in your wardrobe as we head towards autumn, and the beauty of investing in a leather jacket is that you'll be wearing it year in, year out. Take notes from Cindy and add a gold necklace for the finishing touch."
A leather jacket is a timeless staple that every wardrobe deserves, offering just the right amount of coverage without being too heavy, making it a go-to for both the warmer and cooler months. Plus, you can layer it over dresses or shirts to add a vintage edge to your daytime look. And pairing this style of jacket with flared jeans is such a simple move, yet it's really effective. This combination is even suitable for evening meals, parties, or laid-back special occasions.
Sign up for the woman&home newsletter
Sign up to our free daily email for the latest royal and entertainment news, interesting opinion, expert advice on styling and beauty trends, and no-nonsense guides to the health and wellness questions you want answered.
Black heeled boots are the finishing touch that grounds this outfit, providing both height and glamour. We've seen plenty of a-lister wearing heeled boots in the recent months, and we are eager to integrate this style into our warm weather looks. From Amal Clooney's knee-high boots, to Jennifer Aniston's suede pair, they are certainly making a comeback. And they are versatile enough to account for the unpredictable weather, from chilly mornings to warmer afternoons.

Molly is a fashion writer for woman&home, whose journalistic career began with her enthusiasm for fashion. Having always been an avid writer, she has contributed to publications covering a variety of topics.
After graduating from her master's in Fashion History and Cultures, she transitioned to teaching at London College of Fashion, where she taught in fashion studies. Now, passionate about writing on the significance of fashion, she is dedicated to inspiring others through the power of dress.
Molly loves staying in the know with the latest fashion trends, and following celebrities for inspiration. Outside of work, she enjoys browsing vintage markets, reading a good novel, or trying new restaurants around London.
-
Adidas Sambas have been trending for months now - but Fearne Cotton just wore hers in the most refreshing way
We’re still a few months away from sandal season and Fearne Cotton has inspired us to reach for our Sambas so much more.
By Emma Shacklock
-
I'm a former beauty editor who travels for a living - these are the 9 multitasking products I would never leave home without
I pack and unpack 100 times a year, so only the best of the best makes it into my beauty bag
By Lydia Swinscoe
-
Adidas Sambas have been trending for months now - but Fearne Cotton just wore hers in the most refreshing way
We’re still a few months away from sandal season and Fearne Cotton has inspired us to reach for our Sambas so much more.
By Emma Shacklock
-
Helen Skelton's layered look is giving me plenty of country chic style inspiration this Earth Day
She paired a mocha-coloured jumper with a blue shirt and a pair of wellies by Kate Middleton's favourite brand
By Caroline Parr
-
Helen Mirren's go-to accessory is a royal favourite that makes your outfit wedding season ready
If there’s one accessory we associate with Dame Helen Mirren it surely has to be this - and it’s the perfect piece for special occasions.
By Emma Shacklock
-
Clodagh McKenna’s olive green Zara trousers are under £60 - this springtime essential will get you ditching your jeans
Jeans will always have a place in our wardrobe but a great pair of tailored trousers makes a lovely change and can be equally versatile.
By Emma Shacklock
-
Sarah Jessica Parker's diamante bag is giving her iconic Fendi Baguette a run for its money - and it costs far less
A crystal-covered accessory is a surefire way to add some wow-factor to your outfit
By Matilda Stanley
-
Ruth Langsford's bold cricket jumper is convincing me to wear yellow long after Easter is over
Her knitwear is an easy way to work the butter yellow trend into your wardrobe
By Caroline Parr
-
I've bought this M&S hidden support vest in three colours - it's comfy, smoothing and perfect for summer
For just £12, this everyday base layer comes with plenty of benefits
By Matilda Stanley
-
We're enjoying the sunny spring weather, but a jumper is still essential - Sienna Miller's pastel pink knit is ideal
Spring has arrived, but sunny April weather can still come with a chill. We're taking inspiration from Sienna Miller's pastel pink knit
By Charlie Elizabeth Culverhouse