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1Preppy
Hellin Kay Pair floral cutoffs with a white sleeveless shirt tied at the waist for a sweet, preppy look.
Paige Denim Echo Park White Rose Shorts, $139; paigeusa.com
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2Preppy
Hellin Kay Complement pastel striped shorts with a pink polo. (Popped collar optional.)
J Brand Low Rise Cut Off Shorts, $213 (on sale); mytheresa.com
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3Preppy
Hellin Kay A simple white button-down paired with these printed shorts creates a sophisticated and classic look.
Mango Ikat Print Shorts, $22.99 (on sale); mango.com
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4Preppy
Hellin Kay Style pale pink shorts with an eyelet blouse and summer sandals for your next picnic in the park.
Zara Colored Denim Shorts, $29.99 (on sale); zara.com
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5Preppy
Hellin Kay Cuffed white denim shorts feel nautical when worn with stripes and a panama hat.
J.Crew White Denim Shorts, $79.59; jcrew.com
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6Preppy
Hellin Kay Play up the patriotic vibe of these shorts with a chambray top.
Isabel Marant Étoile Dinky Embroidered Star Shorts, $168 (on sale); matchesfashion.com
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7Preppy
Hellin Kay Match with a scalloped blouse and these floral print shorts are garden-party-ready.
Red Valentino Floral-Print Denim Shorts, $115 (on sale); theoutnet.com
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8Preppy
Hellin Kay Throw on a baseball hat and a simple tee for a look that's All-American.
Frame Denim Le Cutoff Shorts, $143 (on sale); matchesfashion.com
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9Preppy
Hellin Kay Denim shorts with clean lines feel classic when worn with gingham.
Theory Yanima Denim Shorts, $55.01 (on sale); theoutnet.com
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10Preppy
Hellin Kay Colorblock denim adds a playful twist. Style with a plain white tee for a clean look that can be dressed up or down.
Madewell Colorblock Denim Shorts, $98; madewell.com
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11sponsored: tiffany & co.
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12Preppy
Hellin Kay Show off your abs in a cropped top paired with these flirty high waisted shorts.
Topshop Moto Bleach Spot Denim Hotpants, $60; topshop.com
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13Preppy
Hellin Kay Slip-on these shorts and head to the lake. These classic London Boy shorts were made for adventure.
MiH Jeans The London Boy Low-Rise Denim Shorts, $138.60 (on sale); net-a-porter.com
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14Minimalist
Hellin Kay Wear cream colored shorts with a gray T-shirt and minimal jewels for as easy every day look.
Stella McCartney Stretch-Denim Shorts, $174.98; theoutnet.com
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15Minimalist
Hellin Kay Faux-leather shorts elevate an all black ensemble.
Stylestalker Future Echoes Shorts, $99; shopbop.com
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16Minimalist
Hellin Kay Coated shorts look sophisticated and chic when paired with a silk blouse and pumps.
7 For All Mankind Coated Shorts, $178; shopbop.com
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17sponsored: tiffany & co.
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18Minimalist
Hellin Kay Mid-thigh denim and a sheer tank is ideal Saturday attire.
7 For All Mankind Mid Roll-Up Shorts, $158; shopbop.com
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19Boho
Hellin Kay Printed and frayed, just add a flowy blouse to channel your inner bohemian.
Current/Elliott The Boyfriend Print Denim Shorts, $254 (on sale); mytheresa.com
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20Boho
Hellin Kay Tribal embroidered shorts add a playful, free-spirited touch.
Zara Ikat Embroidered Shorts, $49.99 (on sale); zara.com
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