Nantucket, MA : Lucky Magazine

Addison Craig

This Florida transplant quietly opened last year in an out-of-the-way shopping center. It presents an encyclopedia of shoe lines—Maloles, Botkier, Sigerson Morrison—almost all of which are new to the area.
2 Washington St., 508-228-1899, addisoncraig.com

Belongings

Masterminded by an architect/interior designer whose first shop was in Turks and Caicos, Belongings telegraphs a tropical-island decor sensibility. Yet it seamlessly works in an East Coast maritime tradition as well: Antique telescopes and sea flag throw pillows are placed alongside pieces of coral and opalescent vases.
23A Old South Wharf, 508-228-0677

Blu

Roughly the size of a hallway, this boutique specializes in comfortable, easy-to-wear staples: There are Bettye Mueller flats, loads of denim lines, plus simple Inhabit cashmere sweaters and tanks.
5 S. Water St., 508-325-6980

Current Vintage

The premise may seem a bit too cute, but owner and former restaurateur Elisabeth English pulls off selling both wine and vintage clothing in a totally non-corny way. It's primarily because the garments on offer are rare '60s and '70s Lilly Pulitzer dresses, along with a smattering of Pucci caftans and embroidered Mexican tops. And there aren't enough suppliers of nice wines on Nantucket, so the liquor component is wildly convenient.
4 Easy St., 508‑228-5073, currentvintage.com

Erica Wilson Needle Works

One side of this classic Nantucket boutique is devoted to needlepoint, from pre-painted belt canvases to endless racks of thread (useful, if you need a beachtime activity). The other is stocked with on‑point vacation-centric fashion and jewelry.
25 Main St., 508-228-9881, ericawilson.com

Eye of the Needle

Though it has a storied blue blood legacy (its other outposts are in Boston and Palm Beach), this long-standing shop, complete with leopard-print carpet and white wicker chairs, skews much more jet-set hippie these days. Aside from a huge collection of Melissa Odabash bikinis, there are embellished blouses and woven heels for evening.
14 Federal St., 508-228-1923

Gypsy

Former stylist Paola Gonfrade, who owns a boutique of the same name in Palm Beach, has transformed a sunny bungalow into a serious fashion destination. It's replete with the best pieces from the best lines—Zac Posen dresses, Lanvin ballet flats, Rick Owens leather jackets—and whatever doesn't immediately blow off the racks wends its way to the secret second-floor outlet.
20 Federal St., 508-228-4404

Murray's Toggery Shop

The now-iconic Nantucket Reds made their debut here back in 1945. The ground floor is devoted to every conceivable permutation of the cotton pants (including dresses, shorts, and skirts), while upstairs, there's a Crayola 64-pack selection of another preppy standard: Jack Rogers leather sandals.
62 Main St., 508-228-0437

Patina

Owned by Ted Muehling's sister Carol, Patina carries as deep a selection of the famous jeweler's stunning necklaces and bud vases as you'll find anywhere outside of Muehling's Soho store. The space is sun-drenched and lovely, and all of the necklaces and earrings are artfully placed on antique postcards and then positioned next to Lars Andersson sweaters and delicate shawls from India.
23 Centre St., 508-228-7118