Five Americana Vacation Looks, From the Boardwalk to Big Sur

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Asbury Park

Nothing is as boardwalk casual as a pair of tattered jean shorts. Amp up the look with stellar accessories and a streetwear-cool tee.

Shop it now: Steven Alan bag, $325; Adidas Originals shirt, $45; Ksubi shorts, $189; Iam by Ileana Makri bracelet, $570; Aquazzura sandal, $695

Santa Fe

Keep cool in the heat with neutral colors that pay homage to the surrounding desert. A patterned skirt anchors this look, which is punctuated by colorful accessories.

Shop it now: Gianvito Rossi booties, $950; Wilfred top, $65; DKNY skirt, $395; Samantha Wills earrings, $164; Marni necklace, $430

Big Sur

For a trip that's heavy on adventure, versatility is key. Here, a swimsuit acts as a top 'til it's time to jump in while rugged boots ensure you're ready for any terrain.

Shop it now: Madewell backpack, $248; Hunter boots, $175; Ack swimsuit, $152; Zara shorts, $26; J.Crew cardigan, $240; Nixon watch, $125

New Orleans

Take a cue from NOLA's bright buildings and dress in bold colors and patterns. Pull it all together by rooting the look in the same few colors—yellow, red, and white.

Shop it now: Marni pants, $833; Zara top, $40; 3.1 Phillip Lim heels, $417; Christian Louboutin bag, $2,995

Portland, Maine

It's all about a classic nautical theme here. Mix navy, red, and white with gold accessories in this look, which gets its casual cool from a pair of clean sneaks.

Shop it now: Heidi Klein bikini top, $150; Kenzo skirt, $325; Gemma Redux necklace, $175; Charlotte Olympia clutch, $1,165; Steven Alan sneaker, $380