Daisy Dukes. Cut-offs. Jorts. Denim shorts have had many iterations over the years, and they’re never out of style for long – if at all.
But if you think the style is too young or too hard to replicate in a way that doesn’t feel like elevated enough, we’re here to dispel those fears.
Stylist to stars such as Oscar winner Mikey Madison and appearing on Selling Sunset, Kelsey Norris told woman&home that the trick to approaching a shorts-led outfit is to forget about the outdated rules so many seem to stick to.
She says, “Just like art, cinema, language, any new business venture, subject, or field – the more you think you know, the more you realise you don’t… Why not apply this philosophy to denim shorts? Try light wash with boots, dark wash with heels, a belt and a blouse, no belt loops at all, pocket shapes – worn in, worn out.”
Here, she shares top tips for elongating the leg and adding touches of boho style or elegance to a simple pair of denim.
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Good Standard Raw Hem Denim Bermuda Shorts
Longer Bermuda shorts are everywhere right now and they are perfect for anybody that prefers a little more leg coverage.
Amazon Essentials
Women’s Mid-Rise Slim Fit 4″ Denim Shorts
A fuss-free design and minimal trim at the bottom give this pair a slightly smarter feel. Wear with a cami and a blazer for added polish.
32 celebrity denim shorts looks
Jennifer Aniston shows us the basics
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She’s known for her understated and unfussy style, often rocking a simple white tee or other capsule collection essentials. And that’s why Jennifer Aniston makes a strong case for keeping a classic pair of blue wash denim jeans to hand.
The right kind of oversized – so they don’t look too revealing, while still flattering her legs – Jennifer’s relaxed hem shorts and simple white vest get an elevated touch thanks to her choice of shoes.
Josh Hembry, of vintage fashion retailer Messina Hembry, explains why Jennifer’s oh-so-simple look is so impactful.
“For a more cool and casual aesthetic, opting for strappy heels or sleek mules will instantly elevate the outfit and take it from day to night.”
Victoria Beckham brings the glamour
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Style icon Victoria Beckham offered a masterclass in making a couple of casual items look like a chic, well-thought-out look.
Pairing some blue denim short-shorts with a loose sweater and a flowing scarf, Victoria was able to dress up the style without overpowering it. The choice of black, leather peep-toe boots also gave the look a more versatile quality.
Duchess Sophie plays with tonal shades
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It might seem like a fairly obvious statement to make, but Duchess Sophie proved how a relatively straightforward outfit can still look intentional and flattering.
Wearing colors that clash or that look like you’ve just thrown on the first things that you found can cheapen the effect of your outfit, but keeping things tonal – such as her darker blue jeans paired with a light blue scoop-neck tee – makes everything look planned.
Extra points here as Sophie even kept her bag to a similar color palette – an easy and smart way of bringing an effortless look together in a polished way.
Kate Moss mixed rock with classic
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Kate played with different styles coming together for a look that’s both chic and rebellious, pairing short black shorts with dark tights with a pair of leopard print heels for that classic rock chick vibe she so often exudes. However, what makes this look truly versatile is the addition of a smart black jacket.
Elongate your legs with a simple trick like Natalie Portman
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Celebrity stylist Kelsey Norris advises choosing cuts that flatter your own height and features. You might love an outfit someone else has worn, but if you’re much shorter, you might need to adapt it slightly to work for you.
Kelsey explains, “Choose footwear that shows more skin to give the illusion of longer legs… a boot will cut off the line and make a short person look shorter.”
Here, Natalie’s low-rise sneakers and lack of socks elongate her legs, especially useful considering she opted for baggier, oversized shorts.
Michelle Pfeiffer’s classic retro look
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Want to make a couple of simple, everyday pieces look retro and chic? Follow Michelle Pfeiffer’s lead here.
She pairs a classic pair of Daisy Duke mini shorts with a baggier button-down shirt. But by fastening her shirt to reveal a slight hint of her abs, it becomes playful and almost vintage pin-up.
Michelle also deploys the trick of choosing a shoe that shows more skin – making her legs look longer and her taller.
Jennifer Lopez swaps blue jean shorts for white
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Jennifer Lopez put a perfect summery spin on the classic denim shorts by swapping out a blue wash for a crisp white, and pairing them with a burst of summery colors.
JLo perfectly captures celebrity stylist Kelsey Norris’s top tips for giving denim shorts a more elevated feel. “Wear a silk blouse or button-down collar shirt that could be left open or unbuttoned with some chest exposed,” advises Kelsey. “Investment pieces or standout accessories will make the look a bit more elevated.”
Jennifer’s bold hat and open, flowy shirt give just enough flirty summer vibes to turn these denim shorts from something you slip into to beat the heat into a perfect summer vacation outfit.
Pamela Anderson
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Dressed down doesn’t need to feel last-minute or unplanned, and Pamela Anderson offered a masterclass in relaxed-but-impactful styling.
Back during her Baywatch days, the blond bombshell leaned into her beachy persona, wearing a pair of light blue denim shorts with a matching denim shirt.
Double denim can sometimes be tricky to pull off, but with Pamela’s clever styling – such as tying the baggier shirt up around her stomach – it’s a solid look. A subtle addition here, Pamela’s choice of a long necklace helps add a finishing touch to the look without overpowering it.
You can almost imagine her tucking the shirt into her shorts after she was done on the beach and being able to go out to dinner in the same outfit.
Katie Holmes
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Showcasing how to keep denim shorts in rotation during unpredictable weather days, Katie Holmes’s no-fuss blue jeans go perfectly with her cozy cardigan and button-down shirt.
The dark, flat pumps contrasted with the light blue shorts also help to elongate her legs.
Miley Cyrus
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Denim shorts have long had an association with country – think Daisy Dukes from the Dukes of Hazzard or short denim jeans with big cowboy boots at the local bar. There’s something cool and Americana about them, and that’s possibly why they’re having a revival with young stars like Miley Cyrus.
Taking a slice of American country and mixing it with a sparkly, halter-neck top and fishnet tights, Miley subverts the All-American image.
The other benefit of styling denim shorts with a more showy top or accessories is that the statement pieces won’t be overpowered.
Blake Lively
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Blake Lively offered an inspired approach to casual summer style with her denim shorts.
The key to Blake’s look is the balance between the proportions. The baggier shirt, with its relaxed fit and simple pattern, is perfectly offset by the structured, high-waisted denim shorts that have a shorter hem.
This creates a silhouette that’s comfortable without feeling under-dressed or too casual.
Margot Robbie
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At the core of Margot Robbie’s comfy yet chic airport outfit is a timeless combination: a plain white tee and denim shorts.
It’s a combination that lends itself to many interpretations, and Margot’s was perfect for a refreshingly laid-back cool vibe. The distressed denim and casual sneakers give off perfectly imperfect, and the flannel shirt, worn around her waist here, adds a touch of rock chic.
While this might not be why Margot wore the shirt in such a way, the flannel shirt around the waist could be a great tip for anyone wanting a touch more cover up in their shorts.
Lily-Rose Depp
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While Lily-Rose Depp’s outfit might be harder for many to recreate, one key thing she did well, according to celebrity stylist Kelsey Norris, was to work with her proportions.
On the shorter side, Kelsey points out how the actress and model “chose footwear that shows more skin to give the illusion of longer legs. Short shorts paired with a Chanel classic low pump, as she did, or a kitten heel for a little lift and length, can transform your style immediately.”
Natasha Lyonne
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Is it winter? Is it summer? Does it matter? That’s what we take away from Natasha Lyonne’s layered take on wearing denim shorts.
Proving they can be a staple piece that lends well to mixing and matching, the Poker Face star’s distressed, gray denim shorts offer a rebellious foundation to build her outfit on.
The sheer black tights streamline her legs and add an element of sophistication to the frayed shorts, and the tough, structured leather jacket adds a touch of quality.
Heidi Klum
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Heidi Klum expertly showcased how different denim shorts can look and feel.
Her patterned, frayed denim shorts act as the centerpiece of the outfit, paired with a structured, tailored cropped jacket in a classic houndstooth pattern. A contrast of styles and forms immediately make this look feel high-fashion.
The cropped jacket hits at just the right point to highlight her waist and balance the high-waisted shorts, meaning she loses none of her height and is able to show some skin without really revealing all that much at all.
Kelly Rowland
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Kelly Rowland’s outfit is a perfect example of how to make a simple top and denim shorts look polished.
The high-waisted denim shorts and the chunky, patent leather belt cinch her waist, creating a defined and flattering hourglass shape.
Her stacked gold and white bangle, along with the layered necklaces, is the perfect way to bring this simple look together without taking anything away from the core, simple pieces.
Mariah Carey
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Leave it to the ultimate diva, Mariah Carey, to prove that a simple pair of denim shorts can be fabulous.
Mariah proved how versatile the denim short can be with her sporty, luxe mix and matching, opting to pair her denim shorts with a colorful satin bomber jacket.
A pair of very high, strappy heels prove that denim shorts can be dressed up for any occasion.
Kendall Jenner
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If you’ve ever wondered just how far you can take the high-low fashion effect, look to Kendall Jenner.
The supermodel wore a surprising (but surprisingly effective) combination on the red carpet of the 2017 Cannes Film Festival, pairing a simple pair of jean shorts with high fashion couture.
Kendall’s jean shorts, a staple of summer, somehow worked impeccably with the black, one-shoulder Alexandre Vauthier couture top and long train and black pumps.
Chloe Sevigny
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Actress and cool girl Chloe Sevigny’s best looks over the years have proven she can craft her own rules when it comes to fashion – and this extends to how she reimagines a denim short outfit.
Spotted out and about in New York City, the American Psycho actress took seemingly disparate pieces – including a romantic, delicate lace top and rugged, ripped denim shorts – and brought them together in a cohesive and chic way.
Natalie Portman
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The evolution of the denim short is captured perfectly in Natalie Portman’s business-casual look.
The star was spotted wearing a structured, smart blazer, which she paired with frayed, distressed denim shorts. Seemingly at odds with one another on the style spectrum, the combination of the pieces shows how style rules are open to interpretation.
What Natalie’s look does well is having the blazer be slightly boxy and oversized, contrasting with the shortness of the shorts. The result is both relaxed and fresh while being versatile and reusable.
Taylor Swift
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Pop singer Taylor Swift kept her denim short style quintessentially summery and nautical, pairing them with a long-sleeved striped shirt which she tucked into the short shorts to elongate her frame and give a statuesque silhouette.
Madonna
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Pop icon Madonna sported a pair of longer, baggier denim shorts in the late 1980s, and her styling was an inspired mix of reimagined menswear.
Opting for a more relaxed fit, Madonna’s shorts had a vintage feel, and her sleeveless gingham shirt was her way of re-imagining classic western wear.
Tucking her shirt into the shorts with a thick, statement belt created a clean and intentional line, and the coordinated pop of red with her pumps brings the whole look together.
Christina Aguilera
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Modern retro is how we’d describe Christina Aguilera’s sophisticated and memorable outfit.
The star wore a pair of dark blue denim shorts and paired them with a simple tank top and bomber jacket – all very in line with 2000s fashion.
However, the added touch of a headband and white, stiletto pumps helped inject a burst of retro glamour, for a twist on vintage dressing that felt fresh.
Leona Lewis
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British songstress Leona Lewis’s boho twist on denim short styling could be worn everywhere from a festival to running about day-to-day.
The star paired mid-length, frayed light blue jeans with chunky black boots and a simple black top for a look built on dramatic contrasts. While the boots and jeans could almost have a tough, rock edge, Leona’s addition of a sweeping, floor-length crocheted cardigan softened the look and gave a modern hippy feel.
Kaia Gerber
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Cindy Crawford made denim shorts and a white tank top the very picture of the All-American girl-next-door with her Pepsi ads, but decades later, her model daughter, Kaia Gerber, showed how to put a new spin on an old classic.
The young star played with proportions by pairing her cut-offs with a cropped tee, leather jacket and boots.
Nicole Richie
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Fashion designer and reality star Nicole Richie put her own stamp on denim shorts with a look that felt like a perfect mix of boho spirit and rock edge.
Nicole’s rule-breaking styling – pairing a lighter short with darker tights and boots – helped make a dramatic statement, and her choice of flowy fabrics with the rigid shorts and boots gave movement and elevated the look.
Kim Kardashian
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Kim Kardashian’s eclectic outfit is proof that one doesn’t necessarily need to go out and buy new clothes to create a new look.
It’s easy to imagine that Kim, like many of us, had a bunch of separates that she never thought to put together before. 3/4 length denim shorts, a simple black top and a statement, graphic blazer?
While it sounds disjointed, it works. And it’s proof to try and experiment with separates sitting in the closet.
Miranda Kerr
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Denim shorts lend themself to layering, as Miranda Kerr’s effortlessly chic travel outfit demonstrates.
Keeping her look to a series of mixed and matched essentials, Miranda’s simple white top tucked into a pair of blue denim shorts and sheer, black tights gives a streamlined, color-blocked effect.
Draping a black coat over her shoulders adds a touch of sophistication to the dressed-down look.
Jessica Simpson’s Daisy Dukes
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In 2005, Jessica Simpson helped re-popularize the classic Daisy Dukes, a super short pair of denim shorts that were synonymous with the girl-next-door character, Daisy Duke, from The Dukes of Hazzard.
A constant tentpole in summer fashion, Daisy Dukes evolved over time, and are now worn by people of all ages and personal styles, be they paired with chunky boots and leather jackets, heels and strappy tops, athletic trainers and hoodies and more.
Rihanna
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Rihanna expertly paired a classic, slightly oversized white button-down shirt with high-waisted denim shorts for a look that’s truly timeless and easy for anyone to recreate.
Wearing the classic white shirt open with a casual, relaxed drape creates a sense of laid-back chic that is both effortless but also intentional – it’s off-duty dressing but not caught off guard.
The peek of a bright orange top underneath adds a deliberate pop of color, proving that staple pieces can still be personalized and made unique to one’s style.
Dana Delany
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While Desperate Housewives star Dana Delany’s look might feel quintessentially 90s, we can so imagine recreating it today – or any time. It’s the very definition of effortless cool.
A crisp, white shirt worn slightly oversized, Dana tucked the shirt in and rolled the sleeves up to avoid the baggy look overwhelming her. A pair of longer denim shorts might not be as easy to pull off, but Dana pairs them with ballet flats, helping to lengthen the look of her legs, despite the longer hem of the shorts.
It’s a simple base and Dana kept it clean and minimalist, but this look would lend itself to subtle pops of color or luxe accessorizing to switch it from dressed down to dressed up. For example, earrings or a statement watch, or even a more prominent belt, could easily transform it.
Amy Winehouse
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The late, great Amy Winehouse had a voice that traveled through the decades – a ’60s soul in a ’00s character. And her fashion often followed this dynamic.
Amy was known for her love of mini denim shorts in an array of colors, and the more unusual choice of colorful hued shorts helped her forge her modern-retro aesthetic.
