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1 1920s: High-Waisted Honey Getty Images When in doubt, high-waisted shorts and a tank top or one-piece are always an effortless go-to for summer, as perfected in the summers of the '20s.
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L.F. Markey Shop the Look: High-Waisted Cotton Blend Shorts 2
L.F. Markey Shop the Look: High-Waisted Cotton Blend Shorts Wear them as a swimsuit cover-up or with a bodysuit on your summer weekends.
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3 1920s: Duster Cover-Up The duster jacket may be a street-style favorite, but take note from the ladies of the '20s and try it as a swimsuit cover-up too.
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All Saints Shop the Look: Feather-Print Duster 4
All Saints Shop the Look: Feather-Print Duster Wear it in the summer with your favorite swimsuit and then again in the fall layered over a T-shirt and jeans.
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5 1930s: Prints, Please The women of the '30s counted on floral and bold print dresses to stand out during a time of fashion cutbacks due to the Great Depression and the Dust Bowl. The same remains true today: If you're sticking to a budget this season, go for an item that stands out in color and pattern.
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Faithfull The Brand Shop the Look: Rafa Floral Midi Dress 6
Faithfull The Brand Shop the Look: Rafa Floral Midi Dress The perfect printed midi dress to wear from work to the weekend.
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7 1930s: Wide-Legged Flair From day to night to the beach, a pair of wide-leg pants is the perfect base for any summer look.
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Staud Shop the Look: Linen-Blend Wide-Leg Pants 8
Staud Shop the Look: Linen-Blend Wide-Leg Pants Available in chambray or khaki, these high-waisted, wide-leg pants are flattering with a blazer and tank for the office, or a bodysuit on the weekend.
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9 1940s: High-Waisted Bikini Bombshell The high-waisted bikini reigns as one of summer 2019's hottest swim trends. Take note from Betty Grable's beach style and opt for a bright color.
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Palm Shop the Look: Baja High-Waisted Brief Bikini 10
Palm Shop the Look: Baja High-Waisted Brief Bikini A bright shade of orange goes perfectly with a sun-kissed glow. Shop the matching bikini top here .
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11 1940s: All Tied Up Channel the early '40s by tying the ends of your button-down into a knot and pairing with a fun pair of printed shorts.
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Tommy Bahama Shop the Look: Boyfriend Shirt Cover-Up 12
Tommy Bahama Shop the Look: Boyfriend Shirt Cover-Up Roll up the sleeves and wear this as a top or a swimsuit cover-up.
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13 1940s: Summer's New Look Dior's 1947 New Look complete with a full skirt lent for a perfect summer silhouette that still feels glamorous to this day.
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Miguelina Shop the Look: Crochet-Trimmed Maxi Skirt 14
Miguelina Shop the Look: Crochet-Trimmed Maxi Skirt A full maxi skirt that'll look best with a white crop top, bikini top, or bodysuit.
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15 1950s: Sweetheart Meets Bombshell The '50s-favored sweetheart neckline looks best with a fit-and-flair dress that cinches your waist à la Sophia Loren.
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Reformation Shop the Look: Dolci Sweetheart Dress 16
Reformation Shop the Look: Dolci Sweetheart Dress Get the '50s look with one of Reformation's printed sweetheart-neckline dresses.
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17 1950s: Sunbathed Beauty Getty Images Cat-eye sunglasses + a scarf tied as a headband = the perfect accessory equation for a beach moment on level with Grace Kelly in To Catch a Thief.
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Mango Shop the Look: Tiger-Print Scarf 18
Mango Shop the Look: Tiger-Print Scarf Try the look in summer's animal-print trend. Wear it as a headband, bandana, or neck scarf all season long.
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19 1950s: Bare Midriff Rules All Take the full circle skirt out of the 1950s housewife's kitchen and onto the beach by pairing it with a strapless bikini top and flat sandals.
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Solid & Striped Shop the Look: Tiered Midi Skirt 20
Solid & Striped Shop the Look: Tiered Midi Skirt Pair it with a bikini top and you've got an instant beach LEWK.
Lauren Alexis Fisher is a freelance fashion editor and writer in New York. She is the former market editor for HarpersBAZAAR.com.
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