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When the Dutch settled New York City (née Nieuw Amsterdam) in the 17th century, they set up shop on the southern tip of Manhattan, in the area we now call the Financial District, fur trading with the native Lenape. Lower Manhattan has since remained a center for commerce, known for everything from Wall Street and the wholesale fish market on Fulton Street to the vast shopping options it offers today. Find the latest high-end jewelry and custom suiting, discounted designer goods and unique specialty shops, including purveyors of Japanese cutlery and comic books, sprinkled among the area's historic sites and waterfront views.

Just across from the World Trade Center site, New York City shopping staple Century 21 features four floors of designer goods at deep discounts. You may have to weave through crowds and sift through racks to find the hidden wardrobe treasure that's calling your name (and then wait in line to try it on and pay for it), but when you score a slick Versace suit or a stacked Prada pump from last season at 75% off, it's totally worth it.

If you're looking for the latest from designer labels, Lower Manhattan has that, too. The Financial District has a superb selection of fine suiting and professional attire (Wall Street's Gordon Gekko would surely approve). America's oldest clothing retailer, Brooks Brothers, first opened in NYC in 1818. The attentive staff at its downtown store, just across the street from Century 21, can fit shoppers for classic made-to-measure suits and shirts, women's separates and newer favorites like the no-iron shirt and the Thom Browne–designed Black Fleece label. On Broad Street, a few blocks away, the American flagship of Italian luxury menswear line Canali stocks classic tailored suits stitched in Milan. London-based label Thomas Pink, on Wall Street, specializes in shirting and offers a range of fits, bold colors and patterns, and collar and cuff styles.

The neighborhood also offers high-end accessory options, from top-notch leather bags to exquisite diamond engagement rings. French fashion house Hermès, with a downtown location on Wall Street, may make men's, women's and children's ready-to-wear, but many covet the brand's silk scarves and ties and leather goods, like its famed Birkin bag. Iconic New York jeweler Tiffany & Co. recently opened a Lower Manhattan location, housed in a 1907 building on Wall Street with stunning restorations and contemporary additions, like the 75-foot-long metal-mesh-and-crystal floating sculpture. While Tiffany necklaces, watches and tableware offer plenty to see and shop, the store's architecture alone is worth a visit. DeNatale Jewelers, another local must-see jeweler, has been selling classic pieces in New York City since 1908. It offers custom one-of-a-kind engagement rings, brooches and bracelets.

There's more to downtown than luxury boutiques, however. The World Financial Center brings an elegant mini-mall shopping experience to the west side of Lower Manhattan. More than 40 restaurants, retailers and specialty shops, ranging from Gap to eShave to the World Financial Center Greenmarket, line the Winter Garden, waterfront plaza and courtyard. Across town, on the east side, the South Street Seaport has cafés, kiosks, restaurants and shops like J.Crew and Victoria's Secret. On Sundays in the warmer months, Fulton Stall Market takes up residence at the old Fulton Fish Market, which opened in 1822 (the fish wholesalers moved to more modern facilities in the Bronx in 2005). Today, vendors selling artisanal foods, local produce and handmade crafts occupy the historic stalls.

Several specialty-shop gems are located just steps away from the Fulton Market. Pasanella and Son Vintners stocks more than 400 wines—from small, family-run vineyards to established labels—in a charming space, a former ship's chandlery built in 1839, with exposed brick and a tasting room that opens into a private garden. Around the corner, The Salty Paw is the spot for pet owners who want to spoil their puppies and kittens. The boutique specializes in home-baked treats, custom raincoats and pet-carrying messenger bags, and bowls and leashes. It also offers a grooming salon and a day-care service.

Closer to City Hall and the Woolworth Building, electronics superstore J&R Music and Computer World has served the City's consumer technological needs for more than 30 years, selling everything from digital cameras to DVDs to cell phones to stereo systems. A few blocks north, on Warren Street, find alternative baby gear and toys for toddlers with a 'tude at Babesta or shop for top-of-the-line, imported Japanese chef knives at Korin, knife supplier to some of New York City's best restaurants, including Nobu and Moriomoto. CityStore, located in the landmark Manhattan Municipal Building, stocks everything "New York"—from genuine taxicab medallions to lucky NYPD horseshoes. A few blocks south, from its cozy, nearly hidden nook on Maiden Lane, Chameleon Comics sells comic books, graphic novels, trading cards and toys.