Day One: Fifth Avenue
As soon as you’ve stashed your suitcases, head straight for Manhattan’s most fashionable promenade.
10:30 a.m.: Start your shopping engines at Saks Fifth Avenue. Peruse the ever-changing shop windows on the corner of 49th Street and Fifth Avenue before entering the main floor, where you can test out makeup, model the hottest bags, and gush over crazily priced jewels. Catch your breath in the fifth-floor café, SnAKS, which opens at noon. The store’s crown jewel—a shoe department with its own zip code that’s packed with Alaïas and Loubs—is on the eighth floor.
Noon: Purchase something sparkly. Six blocks north is the city’s quintessential luxury boutique, Henri Bendel. Splurge on a new pair of Chanel or Marc sunglasses—you’re going to need some eye protection when browsing the gleaming cocktail rings, clunky resin bangles, and delicate silver chains. And don’t overlook the store’s own jewelry line complete with the trademark brown stripes.
1 p.m.: Dine at “the single greatest room” in New York. Continue a few blocks south to 52nd Street and Park Avenue for an extravagant lunch at The Four Seasons Restaurant, snagging one of the final reservations. Gentlemen, make sure to bring a jacket—or you’ll be wearing one of the restaurant’s.
2 p.m.: Bask in fashion’s brightest lights. Stroll back north to Bergdorf Goodman, a clotheshorse nirvana. Though all eight floors stock front-runners of fashion, the third floor spotlights today’s biggest stars—it’s a Céline, Marni, and Saint Laurent mecca. For menswear, head across the street to the tri-level Bergdorf Goodman Men’s for a whirlwind tour of exclusive ties, notably Marinella and Bergdorf’s private label.
3:30 p.m.: Sample the sophistication of Barneys New York. After a short walk to Madison Avenue and 61st Street, shop around for hard-to-find collections like the elegant Moreau handbags sold here, and here only. Before you leave, indulge in an early afternoon cocktail at Fred’s, the store’s beloved ninth-floor café.
5 p.m.: Rethink the little details. Steps away on 62nd Street is Tender Buttons, stocked with a breathtaking array of buttons, from plastic 75-cent versions to $7,000 antique cuff links. Gertrude Stein (whose collection of poetry gave the store its name) would be thrilled.
6 p.m.: Linger over the lingerie. Trigger some boudoir fantasies five blocks north at La Perla, a lingerie shop rich with fine lace and satin. Pick out an innocent, full-coverage piece or go for something wilder, like a siren-red corset. Either way, the store’s cuts are famously flattering.
9 p.m.: Buy an Apple in the Big Apple. A quick walk down Fifth Avenue, and you’ll stumble upon the enormous glass cube housing the dazzlingly designed Apple Store. Even if you own a PC, this 24-hour laminated spectacle is not to be missed.
Day Two: Midtown and the Upper East Side
Though big department stores take up the most real estate on Fifth Avenue, the biggest trends are born at the flagships of famed designers.
9 a.m.: Drink (coffee) and run. Pop into Capital One 360 Café for a quick caffeine boost. For a banking center, it’s surprisingly modest—and where else can the baristas rattle off interest rates? If Starbucks is more your game, there’s one around the corner on 57th Street.
10 a.m.: Pay homage to Donatella. Louis Vuitton? Christian Dior? It’s hard to know where to start your second day, but we vote Versace, the Medusa-emblazoned landmark known for its sky-high heels and ostrich-leather bags. Head up to the womenswear department on the second floor to drool over va-va-voom dresses.
11 a.m.: Show some respect to Karl Lagerfeld, too. Walk five blocks north to Fendi, an enormous store designed by Peter Marino that’s framed in dazzling white Italian limestone. The 4,000-square-foot space is as eye-catching and slick as the label’s metallic minidresses and slinky blouses.
11:45 a.m.: Lock your eyes on that interlocking-G logo. Around the corner from Fendi is none other than Gucci, where low lighting, European trance music, and mazelike staircases will have you spinning. Don’t miss the men’s skinny trousers or the draping gowns on the second and third floors, respectively.
12:30 p.m.: Have an artful meal at MoMA. Take a much-needed break with lunch at the Modern, the upscale eatery at the Museum of Modern Art, one block west. Torn between marinated lobster and pistachio-stuffed chicken? The prix fixe ($66 for three courses, $76 for four) lets you have a little taste of everything.
2:30 p.m.: Resume the hunt at Bloomingdale’s. It’s equality of the sexes at 59th Street and Third Avenue, where guys can peruse the copious man-bag section or shelves of denim and women can swoon over the comprehensive beauty department on the first floor.
4 p.m.: Don’t be late for Tom Ford. Hail a cab to 70th Street, since the Tom Ford store closes at 6:30 p.m., which is unusual for NYC. Like its hirsute namesake, this over-the-top men’s boutique oozes sultry masculinity.
5:15 p.m.: Get a rock with some history. Stroll down to 64th Street to peruse the offerings at Chanel Fine Jewelry, where some of the designs are still based on Coco Chanel’s original sketches. Unless you’re ready to fork over sums in the five-digit range, this may be a look-but-don’t-buy destination.
7:30 p.m.: Enjoy a hard-earned cocktail. End your wandering a few 6-train stops south at Bookmarks, the rooftop bar at the Library Hotel, near Grand Central Terminal. The bar’s extraordinary views and tongue-in-cheek cocktails like the Tequila Mockingbird make for an excellent nighttime warm-up.
Day Three: Soho
No longer the gritty artists’ district of the 1970s, Soho offers up an unrivaled selection of places to eat, shop, and play.
9 a.m.: Breakfast with the editors. Many stores don’t open until 11 a.m., so ease into the day at the Mercer Kitchen, where fashion arbiters and stylin’ out-of-towners sit side by side while ordering omelettes made with Coach Farm goat cheese ($14).
11 a.m.: Begin with a (relative) bargain. 3.1 Phillip Lim is not only beautiful, it’s packed with well-priced soft blazers and supremely well-cut trousers for men and women.
Noon: Step over to Prada. Channel Anna Wintour as you slip over to Prada’s flagship, celebrated for Rem Koolhaas’s enormous wooden wave, which connects the upper and lower levels. Just as noteworthy are the store’s garments and accessories: beautiful overcoats, bewitching dresses, and this season’s “It” bags and shoes.
1 p.m.: Meet the H&M of Japan. With your bank account busted, shuffle over to Uniqlo, a Godzilla of a store from the Japan-based company. Skip the mediocre collection of athleticwear and children’s duds in favor of the main floor’s prized designer collaborations from Christophe Lemaire, Carine Roitfeld, and the like.
2:15 p.m.: Sample some scents. Head down Broadway to freshen up at Sephora, home to every new lip gloss and scent on the market.
2:45 p.m.: Fuel up on Mexican food. After all that hard work (and, yes, it is hard work), treat yourself to zesty grilled-chicken tacos at Dos Caminos Soho, a hot spot for the fashionable set.
4 p.m.: Take fashion’s pulse. Walk off your lunch with the 15-minute trip to Opening Ceremony, a store with a reputation for predicting tomorrow’s trends. The shop’s owners have been known to spend months abroad culling the latest and greatest—like high-waisted jeans and bustier dresses.
5 p.m.: Stock up on fast fashion. Check out the first American outpost of British chain Topshop, with four floors that house designer collaborations, a large shoe shop, and a whole floor of menswear.
6 p.m.: Toast your purchases. Stroll a few blocks to Thompson and Grand streets, where the James New York hotel’s rooftop cocktail bar Jimmy offers a near-360-degree view of lower Manhattan.
7:30 p.m.: Dine at restaurateur Keith McNally’s masterpiece. Just six blocks east on Spring Street is the celebrity-beloved Balthazar. The bouillabaisse, a Friday-night special, or moules frites will temporarily transport you to Paris. If your budget’s aching, dash into the Balthazar Bakery for brioche with prosciutto ($5) or smoked salmon tartine ($6.50). (It’s open daily until 8 p.m.)
Day Four: Chelsea and the Meatpacking District
Push the envelope by scoping out the avant-garde fashions of these two adjoining neighborhoods.
10:30 a.m.: Jump-start your morning. Take the C or E train to 23rd Street for a caffeinated jolt at Café Grumpy. (They’re one of the first New York cafés to brew coffee with the hi-tech, ergonomic Pour Steady machine.) Nosh on pastries from various Brooklyn bakeries (including vegan and gluten-free treats); you’ll be walking it off soon enough.
11 a.m.: Admire the architecture of apparel. Stroll down to 22nd Street then pass through the huge pivoting door and jagged aluminum tunnel into the cavernous home of Comme des Garçons. You’ll probably be one of the few shoppers, since Rei Kawakubo’s abstract designs aren’t that well known, but the artsy shop clerks and risk-taking garments provide plenty of entertainment.
Noon: Browse chic, mid-priced womenswear. Wander a bit south to Rebecca Taylor’s bare-brick boutique. The New Zealand native’s cozy shop feels like a sanctuary for classically feminine clothes, stocking everything from silk A-line dresses to satin camisoles.
1 p.m.: Grab a burger. Head around the corner for lunch at Bill’s Bar and Burger, a low-key alternative to the Meatpacking District’s high-end bistros. The juicy burgers are made from a custom Pat LaFrieda blend, and the casual dining room will let you recharge for the rest of your shopping day.
3 p.m.: Fancify your footwear. No New York shopping trip is complete without a stop at Jeffrey New York, just a few blocks up 14th Street. It’s one of just two Jeffrey stores in the country, and the massive shoe collection is expertly edited. (But be sure to keep your eyes peeled for the latest from Miu Miu and Chanel.)
5 p.m.: Reacquaint yourself with classic DVF. At the intersection of 14th and Washington streets, you’ll find fashion legend Diane von Furstenberg’s airy shop. The décor, like much of the clothes, is inspired by 1970s glam. Take a load off on a bright-pink couch and watch as a friend tries on a signature wrap dress.
8 p.m.: Show off your swag at a blowout dinner. The industrial-chic Monarch Room, located across the street from Chelsea Market, is as super-stylish as your purchases. Dine on eggplant toast and the spiced duck breast, and get some people watching in to boot.
3.1 Phillip Lim
48 Great Jones St., nr. Bowery
767 Fifth Ave., nr. 59th St.
80 Spring St., nr. Broadway
80 Spring St., at Crosby St.
Bill’s Bar and Burger
22 Ninth Ave., nr. 13th St.
660 Madison Ave., at 61st St.
754 Fifth Ave., at 57th St.
Bergdorf Goodman Men’s
745 Fifth Ave., at 58th St.
1000 Third Ave., at 59th St.
299 Madison Ave., at 41st St.
224 W. 20th St., nr. Seventh Ave.
Capital One 360 Café
968 Third Ave., nr. 58th St.
Chanel Fine Jewelry
733 Madison Ave., at 64th St.
75 Ninth Ave., nr. 15th St.
21 E. 57th St., nr. Madison Ave.
Comme des Garçons
520 W. 22nd St., nr. Tenth Ave.
60 E. 65th St., nr. Madison Ave.
Diane von Furstenberg
440 W. 14th St., at Washington St.
Dos Caminos Soho
475 W. Broadway, at Houston St.
598 Madison Ave., nr. 57th St.
The Four Seasons Restaurant
99 E. 52nd St., nr. Park Ave.
660 Madison Ave., nr. 61st St., ninth fl.
Grand Central Terminal
42nd St. at Park Ave.
725 Fifth Ave., nr. 56th St.
712 Fifth Ave., nr. 56th St.
Jeffrey New York
449 W. 14th St., nr. Tenth Ave.
The James New York15 Thompson St. nr. Grand St.
803 Madison Ave., nr. 67th St.
299 Madison Ave., at 41st St.
Saks Fifth Avenue
611 Fifth Ave., at 49th St.
240 Central Park S., nr. Broadway
The Mercer Kitchen
99 Prince St., at Mercer St.
The Museum of Modern Art
9 W. 53rd St., nr. Fifth Ave.
The Monarch Room
408 W. 15th St., nr. Ninth Ave.
35 Howard St., nr. Broadway
724 Fifth Ave., nr. 56th St.
34 Gansevoort St., nr. Greenwich St.
Saks Fifth Avenue
611 Fifth Ave., at 49th St.
555 Broadway, nr. Spring St.
Saks Fifth Avenue
611 Fifth Ave., at 49th St., fifth fl.
143 E. 62nd St., at Lexington Ave.
845 Madison Ave., nr. 70th St.
478 Broadway, nr. Broome St.
546 Broadway, nr. Spring St.
647 Fifth Ave., at 52nd St.