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How to Wear Shorts Like the Classy Lady You Are

In your 20s, when the weather was too hot to handle, it was no big deal to toss on a pair of denim cutoffs and call it a day. Nowadays, shorts are suddenly the hardest piece of clothing to wear, let alone find. Fret not, because these six pairs just so happen to be the ideal combination of appropriate length and on-trend style.

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Flared Shorts

The structured fit makes these age-appropriate (and so cute when paired with a polka-dot blouse and a blazer).

Get the look: Gap ($45); Ann Taylor ($30); Alice and Olivia ($265)

Loose-Fit Shorts

Here’s the secret to making your legs look a little leaner and longer: Wear one size larger than the correct—and probably figure-hugging—size. They’re comfier and your thighs will thank you.

Get the look: J.Crew ($80); Levi’s ($98); Rag and Bone ($85)

Paper-Bag-Waist Shorts

Highlight your middle, while also maintaining ample coverage, with shorts that have some sort of detail at the waist, like a paper-bag tie. Whatever you do, stick with a loose silhouette that moves and tuck in your top to maximize your pair’s waist-flaunting powers. 

Get the look: Ann Taylor ($25); BCBGeneration ($58); Parker ($178)

Distressed Boyfriend Shorts

Many apple-shaped gals are blessed with great legs, making them the perfect candidates for denim cutoffs. Where the waist is concerned, look for a rise that hits at your narrowest point and smoothes everything out, and go for styles with some kind of distressing or detail on the lower half, drawing the eye away from your midsection.

Get the look: Old Navy ($20); Abercrombie & Fitch ($58); Anthropologie ($228)

Denim Cutoffs

OK, we’re not saying you can wear denim cutoffs to work, but this outfit is a fun option for Friday-night drinks. Look for a pair that reaches halfway down your thighs and top it off with an off-the-shoulder blouse.

Get the look: Topshop ($60); Levi's ($70); The Great ($225)

Unique Hemmed Shorts

Scalloped, ruffled, embroidered… Fancy-hemmed shorts are the new slip dress: They’re equal parts unexpected and elegant, and they’re totally appropriate for a weekend brunch or happy-hour drinks.

Get the look: Madewell ($90); Maje ($250); Chloé ($850)

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