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.
Drink
After six years spent whipping the city into a craft-cocktail frenzy with its pitch-perfect Manhattan variations and handcarved ice cubes, Barbara Lynch and John Gertsen's tippler's haven has, thankfully, loosened up a bit. Once-monthly tiki-themed soirees keep things festive, and groups can now make bar-section reservations during off-peak hours. 348 Congress St., Boston, MA 2210, drinkforpoint.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.
Flair
You don't want your girls in some garish getup out of 27 Dresses. Thankfully, a trip here makes finding the right dresses simple, owing to a tight selection of gorgeous (and, happily, understated) frocks from the likes of Coren Moore, Jenny Yoo, and Lynn Lugo. There are tons of colors, fabrics, and styles, and the service is both professional and patient. 10 Newbury St., Boston, MA 2116, flairbridesmaid.com.
Cheryl Richards
Weddings come—ideally—but once a lifetime. Cheryl Richards makes sure the memories will last. Richards and her equipment dissolve into the background only to emerge with stunning black and white photojournalist-style images capturing the poignancy, humor, and beauty of the Big Day. How good is she? Even if the wedding doesn't turn out to be as perfect as your fantasy nuptials, Richards manages to make it seem as if it were. 224 Clarendon St., Boston, MA cherylrichards.com.
Lumiere
Pike traffic is a proven romance killer. Which is why it's a good thing Newton has its own spot to sip, sup, and swoon. The dining room's billowy fabric sets the tone for a special evening, while the dishes from chef Michael Leviton—juicy Crystal Valley chicken; delicate Rhode Island striped bass with preserved lemon and mint—romance your palate. 1293 Washington St., West Newton, MA 2465, lumiererestaurant.com.
Marathon Sports
Boston is (as a running city should be) chock full of running shops. But none provides the level of personal attention offered at Marathon Sports, where the staff is rigorously trained to labor over every sale. Salespeople here will consider your budget, your running level, and—above all—your foot structure and stride (test runs included) before weeding out your ideal buy from the store's epic stock. 1654 Massachusetts Ave., Cambridge, MA marathonsports.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 .
Jeffrey Jagling, Grettacole
It's sad, but true: Highlights take their toll on tired tresses, and dye jobs gone awry take months to grow out. Thankfully, Jagling is a pro at instantly erasing unseemly streaks and reversing regrettable color. Ladies who can't resist the lure of lightening their locks should keep him on speed dial. We do. Copley Place, Boston, MA grettacole.com.
Mobile Auto Repair Service
They say the proof is in the pudding, or, in this case, the carburetor: Paul Levin is the guy to fix your car. With a vast knowledge of foreign and domestic autos, plus a wicked sense of humor, Levin puts you to task with a thorough Q&A session while narrowing down a diagnosis for your ailing vehicle. Sensitive to tight budgets, he won't take you for a ride. Levin is also completely accommodating. He even offered to look through our car receipts to check the quality and pricing of repair work done in the past. 90 Windom Street, Allston, MA .
Dirk Diegel, Vidal Sassoon
Fortunately for men seeking a haircut, Dirk Diegel of Vidal Sassoon styles and cuts like he was born with comb and scissors in hand. Trained in Hamburg, Germany, Diegel has done his thing at Vidal Sassoon for five years. He's been the manager for more than a year, but he still lavishes his talent on upwards of forty heads a week. If you're lucky enough, you'll let Dirk work his magic on your locks. 14 Newbury Street, Boston, MA sassoon.com.
Cat Silirie, No. 9 Park
A good sommelier knows wine. A great sommelier enlightens all the rest of us. That's what makes No. 9 Park's Cat Silirie the best in town. Each evening her servers are treated to "wine word" classes—"it's grassy, not bright!"—during the staff meal, while diners are gently encouraged to experiment outside their comfort zone—but not beyond their price point. 9 Park St., Boston, MA no9park.com.
Akris
The praise doesn't get any higher: The late Liz Tilberis, editor in chief of Harper's Bazaar, once commented at a charity event in Boston on how elegant the women looked in their Akris suits. The suits are exquisitely crafted in fabrics like double-faced wool, cashmere, silk chiffon, linen, and cotton voile; even those of us who have to work for a living can appreciate that. 16 Newbury Street, Boston, MA akris.ch.
The Bristol Lounge
The best-loved burgers in Boston fall into two camps: the frills-free fast-food type (Flat Patties, Tasty Burger) and the oversize variety topped with high-end accoutrements (Radius, Craigie on Main). Bristol's version, though, stands alon—a layering of juicy beef with a hint of char, aged Vermont cheddar, cool lettuce, sweet tomato, and house-made pickles on a buttery bun. It's the basics done absolutely right—and worth every cent of the $21 it costs. 200 Boylston St., Boston, MA 2116, .
Ideal Manhattan, Citizen Public House and Oyster Bar
Like an antique wing chair done up in a sharp new print, Citizen's spin on the Manhattan hews to tradition while freshening things up. The cocktail starts with the classic recipe (Maker's Mark, sweet vermouth, Angostura), then amps it up with a touch of the unconventional (St. Germain, grapefruit bitters). The final effect? True to the original cocktail's spirit, but tastier. 1310 Boylston St., Boston, MA 2215, .