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Woman & Home
Lifestyle
Molly Smith

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

Header image of Cindy Crawford .

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.

(Image credit: Getty Images)

Shop Cindy Crawford's Look

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."

(Image credit: Getty Images)

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.

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.

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