Bridgehampton, NY: Neighborhoods: luckymag.com

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Barbara Trujillo

This vintage store looks like a film set from an old Western: Trujillo offers an impeccable range of antique turquoise belt buckles and polished fetish necklaces, all against a backdrop of collectible American folk art.
2466 Montauk Hwy., 631-537-3838

Calypso St. Barth

Calypso St. Barth boutiques are dotted all along the East End, primarily because their eponymous collection of silk wrap dresses, tie-dyed scarves, and paper-thin cashmere cardigans works so well at the beach (after all, the chainlet was born in St. Barths).
117 Main St. SAG HARBOR 631-725-1711, calypso-celle.com >

Jacques & Gilles

This boutique inside Andre Balazs' Sunset Beach Hotel has gotten a new name, face-lift, roomier digs, plus a slate of fresh-to-the-island items, like Erés bikinis and Paul & Joe sundresses.
35 Shore Rd. SHELTER ISLAND 631-749-2001

Life-Style

What once was just a pilates studio now houses a full-scale boutique with a jaw-droppingly deep selection of favorite lines like Isabel Marant, Repetto, and Clu.
127 Main St. SAG HARBOR 631-725-1667

Lisa Perry

Fashion designer Perry's collection—which nods to '60s-era icons like Mary Quant—features irresistibly appealing A-line felt dresses, splashed with geometric shapes and numbers. As a nice complement, Perry also sells coffee-table books, fun stationery, and beach towels.
45 Main St. Sag Harbor 631-725-7467, lisaperrystyle.com