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America's Best Shopping Streets

Holiday shopping can be stressful, cutthroat and, at its worst, fruitless. Sometimes the journey to the perfect present starts with an hour-long line at the mall parking garage. Talk about frustrating: You can't take your foot off the brake, let alone step into a store. So, we decided to ditch our wheels and take to the streets on foot.

Spotting glamorous couture on waifish mannequins and gawking at this year's holiday window displays are just two of the allures to "on-the-ground" shopping. And these come free of charge. We think picking presents should be fun, so we've searched far and wide for America's best commercial boulevards. Here is what we've found. On these select avenues, stores are deemed historic sites, sidewalks become catwalks and shopping bags equal merit badges.

In Pictures: America's Best Shopping Streets

Rodeo Drive

Los Angeles, Calif.

Southern California winters are nothing short of nirvana. Once you get past the fact that Christmas lights hang atop palm trees instead of pine ones, the snow-less holidays can be quite enjoyable. There's no better way in L.A. (or more specifically, Beverly Hills) to prep for the gift-giving season then to motor your convertible down to Rodeo Drive for some designer duds. This strip of luxury stores is iconic, gorgeous and as pricey as ever. Nearly every big-name designer has an outpost: Chanel, Fendi, Jimmy Choo, Prada, YSL … the list goes on. But can you put a price on living out your "Pretty Woman" fantasy? Yes you can, and the total comes to: astronomical credit card debt.

Michigan Avenue

Chicago, Ill.

The Magnificent Mile in Chicago [more photos]

Michigan Avenue hosts some of Chicago's most beloved monuments, the Chicago Water Tower, the Art Institute of Chicago, Millennium Park and, of course, the "Magnificent Mile" -- a collection of hundreds of stores and restaurants. The city decorates this wonderful commercial stretch with twinkling lights, while the shops do their part to engineer creative holiday displays in their windows. We admit that strolling Michigan Avenue in Chi-Town's bitter cold conditions can be a challenge, but most shoppers don't mind retreating into department stores like Neiman Marcus and Nordstrom to warm up.

Newbury Street

Boston, Mass.

It's a hard to be glamorous wearing a parka (just ask those Minnesotans). But in New England, there's one premier place to go to learn how to look trendy while staying warm -- Boston's Newbury Street. Despite its regal appearance, this avenue (along with the surrounding neighborhood) was once underwater as part of Boston Harbor until the late 19th century. Considering itself the "Rodeo Drive of the East," Newbury Street's varied architectural styles and wide sidewalks give it a relaxed prestige. In early December, the retailers put on a "Holiday Stroll" -- complete with festive snacks and generous discounts -- to kick-off the shopping season. With a full belly and an even fuller wallet, perusing winter collections is much more fun.

Nicollet Avenue

Minneapolis, Minn.

Some people think that, apart from Chicago, Midwest fashion is non-existent. Those people are flat-out wrong. North of the Windy City, Minneapolis flexes its buying power on Nicollet Avenue, specifically the 13-block stretch called the Nicollet Mall. Here, you'll find stores that cater to a range of budgets. And while the city's indoor Mall of America still attracts some of the most die-hard shopaholics (not to mention cold-weather phobics), we think you'll appreciate the friendly atmosphere exhibited on this urban street. Minneapolis' holiday spirit is best seen during the Holidazzle parades, which proceed through Nicollet Mall every Thursday, Friday, Saturday and Sunday starting at 6:30 p.m. between Thanksgiving and the weekend before Christmas.

NW 23rd Avenue

Portland, Ore.

Portland concocts shopping streets as only the Northwest can: Quirky, fun and chic. The best example of the region's commercial eccentricity is NW 23rd Avenue. Don't expect the skyscrapers of Michigan Avenue or the Italian designers of Rodeo Drive. Here, you'll find homegrown talent -- case in point, shop owner and Portlander Lynn Medoff, who creates fabric wonders in her dress boutique Lena Medoyeff. There are also special-interest boutiques, like The Hip Hound, which caters to dog lovers. Plus, Portland's easygoing attitude makes shopping along NW 23rd Avenue much less stressful.

Fillmore Street

San Francisco, Calif.

Photo by the Fillmore Merchants Association [more photos]

Counterbalancing New York as a coastal heavyweight, San Francisco (with some assistance from Los Angeles) establishes West Coast culture. However, shopping in San Fran is surprisingly decentralized: While the Union Square area hosts the most recognizable stores, Fillmore Street is the best place to catch the up-and-coming trends. The stretch between Jackson Street and Geary Street is lined with retailers and eateries, waiting to be explored. And unlike other commercial areas, Fillmore appeals to those with varied interests; it has three quaint bookstores, three flower shops and even three hardware outlets scattered among the upscale clothiers. Like Boston's Newbury Street, Fillmore Street gets into the spirit with a "Holiday Stroll" in December, when you can enjoy festive entertainment, sweets and discounts.   

King Street

Charleston, S.C.

While many consider Atlanta to be the shopping destination of the South, we find Charleston to be much more appealing. In our opinion, Buckhead's mega-malls can't compete with the charms of King Street. This historic avenue pulses with pedestrians in search of the perfect outfit or gift. Beautiful buildings house big-name brands like Apple and Banana Republic; however, it's the number of family-owned boutiques and male clothiers that really distinguishes King Street. Gentlemen should head to Bob Ellis for shoes and M. Dumas & Sons for apparel, as both are third-generation family-operated Charleston landmarks. Although King Street bustles with pastel-clad patrons particularly in the spring, you'll find Southern hospitality persists year-round.

M Street NW

Washington, D.C.

Most people don't come to Washington, D.C. to shop. Capitol Hill politics dominate the city's social scene. But, take one look at C-SPAN, and you'll see the congressmen aren't dressing too shabby these days. There's only one place to go for the latest styles, and that's M Street NW in the classic Georgetown neighborhood. With its Wisconsin Avenue offshoot, the M Street area hosts preppy mainstays like Ralph Lauren, Vineyard Vines and Brooks Brothers, as well as an assortment of dining options. The crowded thoroughfare has seen many of its independent retailers replaced by luxe brands like Michael Kors and Barbour. But you can still find several sovereign shops -- such as Wink and Sangaree -- holding their own among their new neighbors. This year's winter shoppers will relish "Merriment in Georgetown," a 12-day event featuring holiday-themed food and, of course, shopping specials.

Las Vegas Boulevard

Las Vegas, Nev.

This is perhaps the most exhausting street on our list, but we promise that Las Vegas Boulevard (otherwise known as the Strip) is well-worth a visit. Sin City's main thoroughfare is lined with a multitude of palatial casino-resorts, and nearly each one contains a labyrinth of shops that could put your local mall to shame. Plus, meandering these commercial corridors is like traveling around the world and finding the same contemporary styles. Our favorite venues on the Strip are the Forum Shops at Caesars, the Grand Canal Shoppes at the Venetian, the über-luxurious Via Bellagio and the brand-new Crystals at CityCenter. All we can say is that we hope you hit the jackpot, because Vegas will certainly show you how to spend it.

Fifth Avenue

New York City, N.Y.

Classic, iconic, majestic … Fifth Avenue is America's premier shopping street. With old monuments like Tiffany & Co. and new ones like the Apple Store, this avenue's Midtown stretch validates commercial success. A company that secures a Fifth Avenue address is making a statement to the world that it has "made it." And the payoff is that consumers can find many of their favorite brands on one street, carefully aligned like dominos. We recognize that the Upper East Side's Madison Avenue also demonstrates a fashionable flair, while SoHo's trendy designers cater to the uniquely hip. But in our opinion, Fifth Avenue still reigns supreme. Even if you aren't looking to buy, at least pass by Bergdorf Goodman, Lord & Taylor and Saks Fifth Avenue for a peek at their holiday window displays.

More Photos of America's Best Shopping Streets

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