Stel's
In a highly competitive retail environment, Stel's refuses to play it safe. Instead, it cultivates an always cutting-edge cast of emerging and indie designers (most of them found only here): Alexander Wang, Rachel Comey, Society for Rational Dress. The spot-on buying ensures that one stop will produce all your staples (tees from Coven, denim by Rogan) as well as that truly standout item (like a Gary Graham leather vest). 334 Newbury St., Boston, MA 2115, .
Intimacy
Oprah's a fan, and so are we. Here's why: Inside the luxuriously appointed dressing rooms at this lace and silk emporium, bra specialists give no-pressure, tape-measure-free assessments (get past the fact that they're handling your goodies, and you'll find their approach rather effective). They then lay out scads of sexy yet practical possibilities from the likes of Aubade, Simone Péréle, and Chantelle. Customers leave with bags full of underpinnings that aren't just pretty, but actually—mercifully—fit, too. 100 Huntington Ave., Boston, MA 2116, myintimacy.com.
Natale's
If The Thomas Crown Affair—vintage McQueen version, please—taught us anything, it's that there's no better sandpaper for a man's image than a tailored wardrobe. That kind of polish is stock-in-trade at Natale's, which for four decades has been turning fine Italian fabrics into custom-fitted business and casual wear, complemented by a seemingly endless selection of high-end shirts and ties. The results: seriously smooth. 2001 Washington St., Hanover, MA 2339, natalesofhanover.com.
Bloomingdales
The heart of the capacious first floor at the new multimillion-dollar Bloomingdale's in Chestnut Hill is its smartly laid-out, wholly welcoming cosmetics department. Hard-to-find brands include Clé de Peau and Trish McEvoy; personable, informed, and refreshingly nonpushy salespeople make for zero-pressure lingering; and real-world lighting means it's no shock when your $23 cobalt blue Dior mascara turns out to be very blue, indeed. The Mall at Chestnut Hill, Chestnut Hill, MA 2467, bloomingdales.com.
Dorfman Jewelers
Yes, there's loads of ice on hand here, in the form of Patek Philippe timepieces and Henry Dunay necklaces, but the warm and patient service at Dorfman will thaw any notion that buying big-time bling is a daunting endeavor. In business for seven decades and counting, the family-owned jeweler caters to both Beacon Hill bluebloods and a younger, funkier clientele with diamonds and pearls aplenty, vintage-inspired house lines, and New England's only Van Cleef & Arpels salon. 24 Newbury St., Boston, MA 2116, .
Alan Bilzerian
Though they're usually the last thing you put on, shoes make or break your outfit—and Alan Bilzerian does his best to make sure that you come out on the right side of that equation. He's got a healthy lineup of casual, never-juvenile footwear by Marséll and Corvari, but it's his world-class dress shoes that really take things up a notch: crocodile Alberto Fasciani laceups, Carpe Diem bucks with handcut laces, and Paul Hardin handpainted shoes with stitched toecaps. 1217 Centre St., Newton Centre, MA 2459, alanbilzerian.com.
Lululemon Athletica
Because the pants are preshrunk and consummately flattering. Because the tops are sexy and comfortable. Because (heads up, yoga dudes) the men's apparel is styled like normal, nonhumiliating athletic gear. And because Lululemon's eco-friendly workout mats, gym bags, and other yoga accessories mean that you can strike a pose, discover your center, and leave behind the outside world—in more or less the same pristine shape in which you found it. 337 Newbury St., Boston, MA 2116, lululemon.com/boston/newbury.
Gretta Luxe
Chloé dresses and Balenciaga bags are just two style-savvy suburbanite mainstays found on the racks at Gretta Luxe. Owner Gretchen Monahan travels to New York, Paris, and Milan to bring home exclusive high-fashion apparel and recently debuted a line of knit separates; manager Katie Faessler plays resident style coach, recommending the right Zac Posen top to wear with your new Matthew Williamson embroidered skirt. 94 Central St., Wellesley, MA 2482, grettaluxe.com.
Parlor
Yes, we know: We look cute today. We looked cute yesterday, too. But really, we can't take all the credit. We had help from best-friend team Kelly DiNisco and Nilda Martin, who stock pleasingly anti-prep clothes and accessories out of New York and L.A.: Porridge wrap dresses, Nicholas K. trenches, and in-demand Tag Jeans among them. Prettying your pals? Why, that's what friends are for. 1248 Washington St., Boston, MA 2134, .
Crossing Main
Once a land overrun with whale belts, Hingham is casting off its preppy past. Leading the charge is Crossing Main, a fashion-forward boutique that sells sophisticated clothes, shoes, jewelry, and handbags. On hand are frilly Tracy Reese dresses, bright hibiscus-print shifts by Milly, Tibi tunics, and quasi-bohemian dresses from Nanette Lepore. So if you're still putting off that wardrobe overhaul: Give your surplus Lilly Pulitzer to Goodwill and embrace the new soccer mom chic. 5 Main St., Hingham, MA 2043, .
Adamas Fine Jewelry
Maybe even more so than diamonds themselves, Anto Aboyan and Veronica Sagherian are good friends for a girl to have. The brother-sister team's Newton Highlands shop carries in-demand, limited-circulation designers like Pascal Lacroix, Bergio, and Gurhan. The real gem is their house line: The delicate precious pendants, chandelier earrings, and signature stackable rings in three shades of gold are hard to resist. Just ask Eva Longoria and Nicolette Sheridan, who have donned Adamas on Desperate Housewives. 23 Lincoln St., Newton, MA 2461, adamasfinejewelry.com.
Long's Jewelers
If the accessories you keep in heavy rotation include a diamond-studded Leslie Greene bracelet, cultured Mikimoto pearls, and an arty Casa Gi ring, chances are you're a Long's customer. This branch of the esteemed local chain stocks more than 50 diamond, fashion, and bridal brands, as well as a collection of exclusive estate and vintage pieces. Flashy not your thing? Pick up a sleek timepiece by top-tier watchmakers like Cartier or Baume & Mercier. 250 Granite Ave, Braintree, MA 2184, longsjewelers.com.
Dorfman Jewelers
When bigger means better (and rare is the instance it doesn't), Dorfman majorly rocks the block. An ever-growing roster of exclusive high-end, high-drama designers—including Vhernier, Patek Philippe, and a new Van Cleef & Arpels salon (one of just 8 nationwide)—ensures your diamonds, pearls, and assorted gemstones outshine the competition. There are plenty of subtle pieces here, too, but where's the fun in that? 24 Newbury St., Boston, MA 2116, .
Cross
Parents, face the facts: Bics and Trapper Keepers are way over; your kids wouldn't be caught dead with them. Today's junior scholars want Cross's ultracool chrome-plated Tech3 pens, vividly colored goatskin envelopes, and canvas totes in groovy blue-wave, pink-swirl, or neutral-flower patterns. The bright side: The last two items at least still hold a lot of homework assignments. Zero Brattle St., Cambridge, MA 2138, cross.com.
Vizio Optic
Hey, four eyes: Glasses don't have to be unsightly. Vizio Optic optometrist and co-owner Dr. Galina Rabkin carries more than 1,000 pairs of rimless lenses, titanium frames, and bejeweled plastic specs from hundreds of brands like Bulgari, Prada, and Porsche. Chic prescription shades come from such giants as Mosley Tribes, Beausoleil, and Face Face. See for yourself: You'll look fantastic. 11 Harvard St., Brookline, MA 2445, viziooptic.com.