7 It Girl-Vetted Outfits That Make Cigarette Jeans Look Cool

Reflecting over the last year, there have been signs that the baggy jeans phenomenon was on its way out. Celebrities shelved the wide-leg jeans they wore every day in 2024, and brands started showing indie-sleaze skinnies on their runways. That has left the door open for the return of cigarette jeans, a slim-but-not-totally-skinny Goldilocks style that has the potential to be 2026’s defining denim trend.

Characterized by their slender silhouette and straight cut from knee to ankle, resembling the cylinder they’re named after, cigarette jeans rose to popularity in the ’80s as a minimal alternative to ‘70s flares. It’s a similar pendulum swing to what we’re seeing now: After years of Gen Z’s signature Big Pant, Tiny Top outfit formula and stars like Katie Holmes in jeans so baggy they look like maxi skirts, fashion is now leaning towards cleaner lines and slimmer fits. (See: Dior, Balenciaga, Brandon Maxwell, and Khaite’s Spring 2026 collections.)

That said, cigarette jeans trending today won’t be an automatic “yes” for everyone. Their renaissance may even be cringe-inducing for some, conjuring memories of acid-washed pairs worn with Converse high-tops and perms. For those who weren’t alive during their initial boom, they may not know where to begin with styling jeans that don’t blow in the wind.

To that end, we’ve curated seven actually chic, easy-to-recreate outfits featuring cigarette jeans, worn by It girls through the ages. Who better to offer tips on styling the slim-ish denim than the women who can make any item look cool, from today’s most powerful tastemakers to those who first popularized the style three and a half decades ago?

Cindy Crawford: Cigarette Jeans With a Leather Blazer and Ankle Boots

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To kick things off, we have Cindy Crawford back in 1991, wearing light-wash cigarette jeans with a black leather blazer, a dark turtleneck sweater, and brown leather, pointed-toe Chelsea boots—the perfect complement to a dark chocolate-colored suede belt. The styling will work just as well today, especially considering that chocolate brown is a top color trend and leather blazers are a wardrobe classic on par with trench coats.

Kendall Jenner: Cigarette Jeans With a Cropped Coat and Ballet Flats

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Kendall Jenner, arguably the minimalist style icon of the 2020s, was an early co-signer of the modern cigarette jeans renaissance. In May 2025, the model approached the straight-leg black denim by teaming it with a simple suede jacket and black ballet flats. If you look closely, you’ll see her shoes are made of pony hair, a burgeoning textile that’s nipping at the heels of the suede trend.

Carolyn Bessette-Kennedy: Cigarette Jeans With a Black Top Coat and Loafers

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But of course, there’s no woman more synonymous with minimalist fashion than Carolyn Bessette-Kennedy. The late Calvin Klein publicist was revered (and still is to this day) for her uncontroversial, pared-back style that, crucially, never came across as boring. This straight-leg denim, basic black turtleneck, and single-breasted wool topcoat outfit formula is a case in point the fashion M.O. that has made her a forever fashion icon.

Rihanna: Cigarette Jeans With a Fur Jacket and Statement Handbag

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As the arbiter of cool, when Rihanna endorses a fashion trend, that’s when you know the style will stick around. That’s as true of one-strap bags as it is of cigarette jeans. Take a cue from RiRi and reach for a light-wash pair, a graphic faux fur coat in black and white, and a pop-of-color bag. (She opted for a tangerine Fendi baguette bag, which you’re more than welcome to do as well.)

Princess Diana: Cigarette Jeans With a Blazer and Riding Boots

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You know this Princess Diana outfit. You may have even worn a version of it already. Light-wash cigarette jeans tucked into riding boots, paired with a graphic crewneck sweater and an oversized blazer—it’s quintessential of the preppy, aspirational-meets-attainable style that made her the people’s princess and a beloved figure in culture and fashion. The combination still exudes her signature cool-girl nonchalance today.

Halle Berry: Cigarette Jeans With a Leopard Coat and Velvet Top

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Ten years before Halle Berry would slip into a black latex suit and take on the role of Catwoman, she expressed her feline energy in the form of a leopard-print coat (which happens to be an explosive outerwear trend at the moment). Replicate her outfit with a similarly spotted coat, a velvet turtleneck, and a very ’90s-looking pair of wire-frame sunglasses. It’s a clever way to add edge and personality to a more neutral pair of cigarette jeans.

Dakota Johnson: Cigarette Jeans With a Brown Fur Coat and Suede Bag

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Last but in absolutely no way least: Dakota Johnson. The Materialists star is known for integrating fashion trends into her polished but never stuffy, minimal-with-a-twist style. (Did you see her take on triangle scarves?) This look, which just so happens to include straight-leg jeans, captures her fashion ethos perfectly: a plush fur coat, suede tote bag, baseball cap, and lug-sole, top-zip boots that tick off multiple Winter 2026 shoe trends.