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.
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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.
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