The Ultimate Guide Before You Buy

How to Wear Shorts Depending on Your Age

How to Wear Shorts Depending on Your Age

How to Wear Shorts Depending on Your Age

A rise in temps inevitably leads to hiked hems and sheerer fabrics—basically, a general upswing in skin exposure. But unlike skirts and tanks, shorts continue to be one of the trickier summer staples that toe the line of questionable decency and acceptable age-appropriate daywear.

Not all hope is lost, though. The right blend of color, fabric, and cut can turn shorts from a scary thought into a completely wearable option. For proof, we found stars in their 20s, 30s, and 40s+ who have all been spotted rocking shorts to a T. We grouped them by decade and then shopped out look-alike shorts, from Lily Collin‘s ruffled short shorts to Olivia Munn‘s tailored shorts suit.

If you’re in your 20s, there’s more room for experimentation. Be bold and stand out with a vibrant color or textured accents. Once you’ve hit the big 3-0, scale back on embellishments and itty-bitty hemlines. Look to structured silhouettes to elevate your look. In your 40s+? Reach for longer lengths and tailored detailing for a chic, polished spin.

Shop shorts for every age below.

How to Wear Shorts, Depending on Your Age

1 of 18SAV/ Contributor

How to Wear Shorts In Your 20s…

You can still keep things short and sweet in your 20s. Take a cue from Lily Collins and go for something with details like her charming ruffled pair.

In Your 20s How to Wear Shorts, Depending on Your Age

2 of 18Courtesy

In Your 20s…

A bright floral print and pleated ruffles modernize these shorts for the It-girl of today.

JOA | $69 SHOP NOW

In Your 20s How to Wear Shorts

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In Your 20s…

Stick to clean hems and minimal distressing when choosing a denim pair to look age-appropriate.

American Eagle Outfitters | $45 SHOP NOW

In your 20s How to Wear Shorts

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In Your 20s…

Don’t be afraid to try new shapes like this retro print bloomer style.

How to Wear Shorts, Depending on Your Age - In your 20s

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In Your 20s…

Pastel pink + scalloped edges pack a punch for date night when paired with a flirty blouse.

& Other Stories | $55 SHOP NOW

How to Wear Shorts, Depending on Your Age - in your 20s

6 of 18Courtesy

In Your 20s…

An embroidered pinstripe is perfect for weekend brunch when paired with a white t-shirt and your favorite sandals.

Loft | $60 SHOP NOW

Wear Shorts In Your 30s

7 of 18Jean Baptiste Lacroix / Stringer

How to Wear Shorts In Your 30s…

Look to more structured silhouettes to elevate your look-but that’s not to say you can’t play with print or color. Olivia Munn sported a smart shorts suit on the red carpet, proving that you can go bold over 30.

Wear Shorts In Your 30s

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In Your 30s…

An oversized built-in belt flatters by drawing eyes to a trim waist.

Derek Lam | $395 SHOP NOW

Wear Shorts In Your 30s

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In Your 30’s…

Try a linen pair with flair, ideal for hot summer days and beach nights.

Mango | $50 SHOP NOW

Wear Shorts In Your 30s

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In Your 30s…

Try these with an oversized sweater for a cute and comfy weekend look.

H&M | $15 SHOP NOW

Wear Shorts In Your 30s

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In Your 30s…

The ’70s feeling denim short with front pockets is the grown-up version of the summer classic.

Madewell | $70 SHOP NOW

Wear Shorts In Your 30s

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In Your 30s…

A sailor-inspired version with a slightly longer inseam goes seamlessly from summer Fridays in the office to outdoor happy hour post-work.

 

Wear Shorts In Your 40s

13 of 18Melodie Jeng

How to Wear Shorts In Your 40’s +

Reach for longer cuts, like Bermuda shorts, or shorts that boast tailored detailing to pull off the youthful piece while looking age-appropriate. Gwyneth Paltrow was summer-ready, sporting shorts that flatter and lengthen her legs.

Wear Shorts In Your 40s

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In Your 40s+…

Strong tailoring and crisp pleats make these a great choice for work when paired with a clean, crisp white button-down.

Weekend Max Mara

Wear Shorts In Your 40s

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In Your 40s+…

Bermuda is back as seen on the runways of Fendi and Tibi to name a few. Test the trend in a dark navy for an easy summer look.

  1. Crew | $50 SHOP NOW

Wear Shorts In Your 40s

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In Your 40s+…

A chic printed pair with an easy drawstring waist makes for an ideal choice on those lazy, hazy days of summer.

Toteme | $355 SHOP NOW

Wear Shorts In Your 40s

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In Your 40s+…

A tailored striped pair are made for date night when paired with a sleek silk top and espadrille wedges.

Reiss | $245 SHOP NOW

Wear Shorts In Your 40s

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In Your 40s+…

A playful printed pair is positively vacation-ready.

Le Sirenuse, Positano | $210 SHOP NOW