5 Classic Summer Looks, Updated for Today

Trends may come and go, but there are some summer styles that will always look amazing. Here are five summer classics that everyone from Audrey Hepburn to Grace Kelly to Cindy Crawford has worn—and how to make them look modern and fresh today.

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1. The LWD

  • As in, the Little White Dress. It may be impractical (sorry, moms of toddlers), but it sure does look sharp against your self-tan.
  • Wear it now: In the best silhouette for you, made in a summery material like cotton, linen or an eyelet lace. For the daring, try it in a maxi for a Greek Goddess feel. Cocoon Dress, $80; zara.com.
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2. An Oxford & Jorts

  • It’s hard to get sexier than this iconic image of Cindy Crawford rocking the look. Her high-low juxtaposition of a structured men’s top and distressed denim shorts is a summer classic.
  • Wear it now: You want to look polished and classy and not cheap and trashy. So unless you’ve got a 6-pack like Cindy’s, keep your tummy and your cheeks covered. Look for a cropped, boxy oxford that will float over you high-waisted denim shorts. Oversize Button-Down Shirt, $75; madewell.com. Medium Wash Bermuda, $70; mango.com.
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3. Stripes and Skinnies

  • It’s hard to resist a nautical stripe after Memorial Day! No one has to know you don’t own a yacht.
  • Wear it now: Keep the top loose, not fitted, with your favorite white jeans. Bonus points if those jeans crop just above the ankle. Woman’s Modal Linen Striped Short Sleeve T, $20; uniqlo.com. 1969 Resolution True Skinny Skimmer Jeans, $70; gap.com.
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4. A Plaid Sundress

  • A little bit country, a plaid dress (shown here on Mia Farrow) is a sweet way to show a lot of skin (and keep air circulating) and plaid has been a big hit on the runways this year. Don’t save it just for winter.
  • Wear it now: Keep the classic silhouette and choose a bold pattern like a buffalo check or overscale gingham for a modern update. Woman’s Printed Cami Dress, $30; oldnavy.com
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5. A Big Ol’ Hat & Sunglasses

  • Used to be, tans weren’t so chic. Now we know they’re not so good for you, either. Grace Kelly knows the most stylish way to ward off age spots.
  • Wear it now: Choose frames that flatter your face shape in a size or three larger than you’d wear eyeglasses, paired with a wide brim fedora. Catarzi Wide Brim Fedora Hat, $63; asos.com. Vogue Eyewear Sunglasses in Butterfly, $80; sunglasshut.com.

Image credits: Jackie O via WearNothingNew.Typepad.com; Cindy Crawford via Asos.com; Audrey Hepburn via Sartreuse.com; Mia Farrow via HuffingtonPost; Grace Kelly via Sunchasers.com.


#fbf to 1994 (ish) with my buds, @richardwiese and @wendirogerstv Bought that sport coat on sale for about 20 bucks because that’s all I had in the bank. Was 10% wool and 90% “other.” Got caught in the rain with it and smelled like wet dog ass all night.

Nine years ago, I made a vow to live my life based on three guiding principles: Love, Awe and Gratitude. Today, instead of feeling sad, angry or anxious about The Chew’s cancellation, I will look through the lens of Gratitude and thank: My cohosts, @chefsymon and @carlaphall, for being two of the greatest people I’ve ever had the pleasure of knowing. The crew and staff of The Chew for being so dedicated, hardworking and collaborative. Our viewers for allowing us into your homes each day to share a laugh and a recipe — and a cocktail. It’s been a fun run and I am so freakin’ lucky to have been a part of it. Much love, CK ❤️

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