Oona’s
If you lack the patience to sift through piles and paw through racks to find vintage gems, head to this Harvard Square institution, where staffers have done the treasure-hunting for you. Waiting to meet your closet: sweet Twiggy-era shift dresses, a sequined Valentino jacket, and baubles to satisfy every taste, all at not-that-outrageous prices. Guys can get in on the fun, too, with Hawaiian-print shirts, striped ties, and denim jackets. 1210 Massachusetts Ave., Cambridge, MA 2138, oonasboston.com.
Sweet Cheeks
Photo by Alex Lau Local barbecue fiends once faced a split decision: You could hit up roadhouse joints like Lester’s, in Burlington, or SoulFire, in Allston, or go a tier higher at Newton’s Blue Ribbon or Davis Square’s Redbones. Then came this smoked-meat haven, which, true to its Fenway locale, is in a league of its own. The quality of chef Tiffani Faison’s signatures—giant biscuits, fall-apart racks of ribs—hasn’t changed since the restaurant debuted in 2011. 1381 Boylston St., Boston, MA 2215, sweetcheeksq.com.
Commonwealth
Photo provided Commonwealth already had a lot going for it—Full-service market! Parking!—but this spring, the Kendall Square restaurant upped its game further with a sprawling, Broad Canal—facing patio. Anything you order—may we suggest the flatiron steak from Maine’s Pineland Farms?—will be a mere warm-up for the serious ice cream menu, with roughly a dozen creative, homemade flavors. 11 Broad Canal Way, Cambridge, MA 2142, commonwealthcambridge.com.
Regattabar
A knack for luring the top names in the biz has elevated the Regattabar to its rank among the very best in the East. Far from the popular conception of a jazz club (sweaty, smoky), the venue is flush with tall windows and views of Harvard Square that play well with the non-soul-patched crowd. The talent—Grammy winner Irma Thomas and pianist Ahmad Jamal recently did stretches here—is enough to keep hard-core fans more than happy, too. Charles Hotel, One Bennett St., Cambridge, MA regattabarjazz.com.
The Coop
With independent bookstores (and even national chains) falling by the digital wayside, it's all the more impressive that this classic soldiers on. The four-story Harvard Square behemoth peddles both bestsellers and literary classics, as well as arcane treatises on history, philosophy, music, and science—precisely what you'd expect from a store founded by Crimson scholars in 1882. 1400 Massachusetts Ave., Cambridge, MA 2138, thecoop.com.
Poor Little Rich Girl
Photograph by Jared Leeds Score iconic pieces from every era—Edwardian velvet gowns, 1950s sock-hop skirts, and last season's Marc Jacobs babydoll dresses, for starters—at well-below-typical vintage prices at these twin north-of-the-river boutiques. Scarves, shoes, and funky jewelry round out the selection. Bonus: The Cambridge store, between Kendall and Inman squares, has a small parking lot, so you can pop in to browse without feeding the meter. 121 Hampshire St., Cambridge, MA 2139, shoppoorlittlerichgirl.com.
Long's Jewelers
The 900-pound, umpteen-carat gorilla of the region's jewelry scene, Long's caters to North Shore treasure-hunters with 12,500-square-foot showrooms in Burlington and Peabody—and that's on top of five equally brilliant locations elsewhere in New England. With the 130-year-old company growing strong, customers reap the benefits in the form of a dazzling array of designer jewelry (John Hardy, Marco Bicego), rock-solid Swiss timepieces, and gifts that now include the famed Shreve gurgling cod. 35 Cross St., Peabody, MA 1960, longsjewelers.com.
Rizzo Custom Tailor
The Rizzo who clothed Robert Frost and John F. Kennedy is long gone, but his legacy lives on at this venerable Harvard Square haberdashery. Owner and native Calabrian Joseph Calautti walks his customers through three separate fittings as he transforms supple Italian fabric into bespoke garments with the classic kind of born in-it fit that never goes out of style. 66 Church St., Second Floor, Cambridge, MA .
Davio's
We've long lamented the disappearance of the three-martini lunch. But if such a luxury were still to exist, it would go down at Davio's. Since relocating to its current perch in Park Square, Steve DiFillippo's institution of Italian dining has reclaimed a position of power. Well-heeled Back Bay business types shuffle in each afternoon, scarfing down generous portions of pasta with glasses of house-filtered water, on the rocks. 75 Arlington St., Boston, MA davios.com.
The Paramount
For the umpteenth time, the Paramount is the returning champ in this category. Though many have tried, no establishment has managed to beat the restaurant at its game. Of course, a 73-year head start helps. But the Paramount also manages, quite successfully, to be everything to everyone, feeding a neighborhood of twentysomething renters, deans, doyennes, and the kiddie crowd three squares a day. You'll find a line out the door at breakfast, a fine steak frites at dinner, and a smile on everyone's face at all times of day. 44 Charles St., Boston, MA 2114, paramountboston.com.
Highland Kitchen
We could give this award solely on the merits of Highland Kitchen's tangy, saucy shrimp and grits. But there's so much more to love. Teeming with noisy families and rumpled Camberville denizens, Highland on Sunday mornings is the antithesis of the fussy, overdressed, brunch-is-a-verb scenes of the South End and Harvard Square. Come unbrushed and unshaven, order up a "biggie" mimosa, fried green tomatoes, and those grits, and you may never want to brunch the other way again. 150 Highland Ave., Somerville, MA 2143, .
Diesel Café
While the corporate megapercolators spend millions on ads that pit yuppies against average joes, the Diesel buzzes blissfully along, keeping the emphasis on the coffee. Tattered banquettes and walls covered with funky artwork provide a quirky welcome to Davis Square caffeine addicts. And one sip of the house blend—made from beans that are subtly roasted, not burnt to a crisp—confirms that the brew here is highly habit-forming. 257 Elm St., Somerville, MA 2144, diesel-cafe.com.
Noir
If Bogart and Bacall could hop off the screen of the Brattle Theatre, they'd make a beeline for this sexy Harvard Square gin joint around the corner. There in the inky darkness they'd snuggle into wraparound black vinyl couches, order sultry martini drinks with names like the "femme fatale" and "notorious," and tragically smoke cigarettes (essential for any lounge worth its vermouth). Beautiful friendships have begun over less. The Charles Hotel, One Bennett St., Cambridge, MA noir-bar.com.
Someday Café
A Somerville fixture from the days when Davis was still square, this terminally bohemian café is beloved by an increasingly yuppified local populace that prefers pastries and strong java served by dreadlocked, patchouli-soaked hippies over caramel macchiatos from that Seattle coffee chain. The cozy shop blares alternative rock, sports a gallery of ratty, mismatched seating—including a schoolroom desk and a red velvet lounge booth—and has become a living room extension for tea and coffee connoisseurs of every stripe. Situated next to the Somerville Theatre. 51 Davis Sq., Somerville, MA somedaycafe.com.
Back Bay Yoga, Sweat & Soul Yoga, and Equinox
That Lululemon chose this California-cool yogi to lead hundreds of people in al fresco downward dogs in Copley Square to fete its new Newbury store didn't surprise her devotees: Kaufenberg's challenging hip-hop classes are so much fun, we often forget we're working out. Until the next morning, of course—when we wake up with new aches in our abs and new tunes to download (thanks to her thumping playlists).