While some articles of warm-weather clothing have transcended seasons, like how camis can be layered over button-down shirts once temps dip or slinky slip dresses over turtlenecks, shorts continue to remain the embodiment of summer fashion. There's no other sartorial equivalent akin to slipping on a pair of worn-in denim cut-offs and any top (insert: bikini, off-shoulder top, bodysuit here) to achieve an instant laid-back look that can work for a day trip to Fire Island, weekend errands, or for a cross-country road trip. Like a skirt, a pair of shorts boasts the same kind of freedom and ventilation that you need to survive 100-degree heat, but without the worry of an accidental Marilyn Monroe subway grate moment.
But as much love as shorts get, they're also hated on for their sometimes eyebrow-raising, too-short tendencies that definitely don't meet office dress codes—and if they're really short, style codes of conduct. On the flip side, anything too long can look mumsy (unless you're Gigi Hadid and you can pull off denim Bermudas, no questions asked). And then there's the question of whether you can wear shorts beyond a certain age.
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Well, you can, and you can even wear shorts to work, too, with a pair that features the right cut, the right fabric, and the right styling. As proof, we kept tabs on every time a celebrity wore shorts in the last few months and plucked all the looks that perfectly demo how to wear them at every age and for every occasion. Tailored shorts in your teens and denim cut-offs in your 40s? Yes. The stars know how to defy the norm. From a 17-year-old Lily-Rose Depp in her shorts sweats set to a 48-year-old Julia Roberts in an office-friendly shorts suit, scroll through to see how stars are wearing their shorts.
1. Kiernan Shipka, 16
The starlet still managed to exude youthful sophistication at Coachella. While others went for crochet bralets and racy cut-offs, Shipka went for a sweet butterfly-embroidered denim Valentino two-piece and metallic Stella McCartney platform brogues.
2. Lily-Rose Depp, 17
Style icons take fashion risks. And so as a style icon in the making, Depp took a chance at the La Danseuse photocall during Cannes, and it paid off during. The model struck an unapologetically fierce pose in something as casual as a shorts sweats set (well, as casual as Chanel can be) and brought it to new heights with a pair of sexy red sandals.
3. Sofia Richie, 17
The youngest Richie's summer fashion formula for stylish teens: frayed cut-offs elevated with summer whites, a skinny belt, and strappy sandals.
4. Olivia Holt, 18
The starlet took her tailored high-waist shorts to the red carpet level with a sheer floral blouse (modest in its silhouette, sexy in its transparency) and lace-up sandals.
5. Chloe Grace Moretz, 19
The starlet elevated a basic black tee with a sharp pair of tailored black shorts, an embellished Coach clutch, and delicate black sandals.
6. Kendall Jenner, 20
The problem with short shorts is too much skin exposure, but leave it to Jenner to find a solution—with a pair of thigh-high boots (great for days when you haven't shaved your legs).
7. Gigi Hadid, 21
The supermodel gave her usual off-duty uniform—a crop top and sweatpants—a summery spin with a cropped sweatshirt and shorts set. Matched with canvas accessories, it's a look perfect for both the city streets or for the beach.
8. Olivia Culpo, 24
Culpo expertly brought one of fall's major trends—velvet—into the warmer months with a pair of shorts blanketed in the plushy fabric, pitting it against like-minded shades for a chic tonal effect.
9. Taylor Swift, 26
The pop star completed her style transformation with a teeny pair of inky denim shorts that she gave a laidback-cool vibe to with a simple black tucked-in tee, a cross-body purse, mirrored shades, and white kicks.
10. Elizabeth Olsen, 27
The youngest Olsen channeled her inner #girlboss and suited up in a dove gray Burberry shorts suit, complete with a straw cross-body purse and striped Loeffler Randall platform sandals.
11. Lea Michele, 29
Lea Michele, queen of the Instagram bikini pic, stepped out for the L.A. Dodgers Foundation Blue Diamond Gala in a plunging black romper that perfectly highlighted her toned figure. The 29-year-old singer and actress accessorized with a light, flowy coat, strappy nude sandals, and layered gold necklaces. She pulled her hair back into a low pony and completed the look with a mauve lip.
12. Jamie Chung, 33
Suede shorts sound like an oxymoron (a cold-weather textile with a hot-weather silhouette?), but Chung made it work when she styled hers with a sky blue cold-shoulder top, an open-cuff choker, and strappy sandals.
13. Alessandra Ambrosio, 35
The supermodel has had her fair share of micro-short cut-offs, but she's also been one to take a rather demure approach, like this polished wide-leg pair that she styled with a crisp shirt and booties.
14. Busy Philipps, 37
Knee-length shorts (aka Bermudas) get a bad rep, but Philipps took them out for a chic spin with a white structured shell top, an embroidered cross-body, and stacked heels.
15. Naomie Harris, 39
Harris took the three-piece suit and made it work for day and for warm weather. She upped the style quotient with a crisp white set that she paired with a burnt orange purse (that she carried as a clutch) for a neat dose of color.
16. Reese Witherspoon, 40
How does America's sweetheart wear shorts? Witherspoon prefers prints and color. She recently stepped out in summery pair of yellow floral shorts, and then gave it a sporty, on on-the-go twist with a basic knit, a cross-body bag, white Pumas.
17. Chloe Sevigny, 41
Sevigny is proof that denim cut-offs crosses age boundaries. She gave her frayed denim pair a high-fashion, Coco-approved spin with a darling Chanel tie-neck blouse and a tweed jacket. An adorable novelty Chanel purse in the shape of a movie recorder and preppy loafers completed her French Riviera style.
18. Julia Roberts, 48
Now, this is how to rock a shorts suit. Roberts aced a monochromatic color palette, playing up the contrast with pristine white separates against a black button-down and pumps. Sexy and sharp.