Essential #1: Wide-Leg Denim—This of-the-moment throw-back silhouette looks great when it's a little distressed and either dressed down with a tissue-thin tee or dressed up with a blazer and button-down.
Adriano Goldschmied 23YR Dust Bell Jeans, $199, available at Calypso St. Barth.
Essential #2: Gingham Shirt—We're loving Natalie's bright pop of green contrasted with the pale pink blazer, thanks to its updated Lily Pulitzer vibe. Swap the green out for baby blue and you've still got some majorly harmonious hues going on.
J.Crew Perfect Shirt In Suckered Gingham, $29.99, available at J.Crew.
Essential #3: Pale Pink Blazer—Feminine-meets-masculine at its best, the unexpected pale and girly hue of this menswear staple makes it an ideal piece to throw over a summery frock or elevate a pair of jeans.
Topshop Dusty Pink Premium Seventies Wool Blazer, $190, available at Topshop.
Essential #4: Straw Hat—The epitome of summer, this perfect accessory gives any ensemble an instant laid-back vacation feel, even if you're just chilling in town for the weekend.
Panama Straw Hat, $58, available at BCBG
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Essential #5: Colorful Clutch—Break up the pale and dusty hues with a bold printed clutch, and you're good to go!
Lodis Celestial Diva Clutch Wallter, $185, available at Zappos.