Heartbreak Hill Running Company
On the Esplanade sporting this shop’s iconic logo? You can bet you’ll get a few high-fives along the way. That’s because Heartbreak Hill is a bona fide pavement pounders’ haven, stocked with top-rated sneakers, breathable T-shirts, ergonomic water bottles, and anti-chafe balm (because…sweat). As avid runners themselves, staffers intuitively know what you need along your journey—most important, free running clubs to help you find your tribe. 294 Massachusetts Ave., Cambridge, MA heartbreakhillrunningcompany.com.
Jeremy Ogusky
You get a CSA box from your local farm and you’re on a first-name basis with your butcher, but what about the plates and bowls you set the table with every day? A worthy addition to any Boston cabinet, potter Jeremy Ogusky’s durable, unpretentious pieces can be purchased on Etsy; biannual open-studio days at his J.P. workspace, meanwhile, welcome all to come learn the art of pottery. claycrocks.com.
Eye and Eye Optics
It’s not easy finding a pair of frames that harmonize with your face just so. But if anyone can do it, it’s father-and-son opticians Bobin and Tariq Nicholson, both of whom studied music in college and now bring their artistic vision to this one-stop shop for glasses, contacts, and eye exams. Whether you prefer your specs colorful and funky or sleek and understated, you’ll find them in the cases here—along with warm, personable service that turns a chore into an outing to look forward to. 2271 Dorchester Ave., Dorchester, MA 02124, eyeandeyeoptics.com.
Elizabeth LaDuca
Photographer Elizabeth LaDuca has a knack for making even a dreary day seem ethereal and dreamlike. Each of her shots—from the smallest details to the widest landscapes—seems to glow with a delightful halo of love and light. LaDuca’s organizational skills and experience will keep your event on schedule, but it’s the visual legacy of your special day that will benefit most from her keen eye. MA elizabethladuca.com.
Jimmy’s Shoe Repair
Unlike the stereotypical cranky cobbler who tsks-tsks your shoe care, the guys here don’t judge. They’ll happily fix even the most whittled-down high-heel stub or scuffed-up toe and send it back looking like new. And if you’re in the market for a quirky addition to your collection, be sure to check out the selection of vintage kicks. 42 Prospect St., Cambridge, MA 02139, .
Fête Collection
Receiving a wedding invitation in the mail is always exciting. But when your guests open the envelope and discover, say, a custom illustration of your venue or a folding card with the weekend’s agenda, it’ll be even more so. Along with personalized invitation suites, these Southie-based stationery savants can dream up vellum menus, playful cocktail cards, and foilstamped napkins. And if you don’t have the time (or the calligraphy skills) to address the envelopes yourself, they’ll make sure each one is signed, sealed, and delivered. shopfete.com.
Assembly Showroom
Los Angeles native Matt Gallagher brings the West Coast to the South Shore with Assembly Showroom, a boutique offering casual-cool styles for men and women. With a wide selection of clothing from brands such as Marine Layer, Faherty, and LNA — not to mention ultra-helpful, knowledgeable staffers that make upgrading your wardrobe a breeze — you’re guaranteed to drop in more than once. And your options for visiting are plentiful: Within three years of opening, Assembly already has three locations on the South Shore. Hingham and other locations 24 North St., Hingham, MA 02043, assemblyshowroom.com.
Sweat Fixx
What should you do if you miss pumping iron with your crew, but you’re still not ready to step foot inside a gym? Grab your yoga mat and some optional weights and head to Sweat Fixx for an outdoor fitness class, pronto. Offering al fresco strengthening sessions at its Southie location seven days per week, this woman-owned studio makes it (mostly) painless to squeeze in a low-impact workout filled with squats, biceps curls, planks, and more planks whenever the mood strikes. 323 Dorchester Ave., South Boston, MA 02127, sweatfixx.com.
Fasika Café
From the springy tear of tangy injera cr&_ecirc;pes to the supple pillowiness of raw chopped beef leavened with gobs of fiery-orange spiced butter (kitfo), the tactile pleasures of Befekadu Defar’s traditional (read: silverware-free) Ethiopian fare are just what the doctor ordered to reward your Purell-chafed hands for 16 months of ablutionary abuse. Your gustatory receptors will thank you, too. 51 Roxbury St., Roxbury, MA 02119, fasikarestaurants.com.
J. Press
In a world where trends change daily, this preppy haberdashery recalls the proper Harvard Square of yore. Looking to impress in the boardroom? Try the U.S.-made "Super 120S Wool" charcoal beaded-stripe suit. Need to accessorize your tailgating attire for the big Harvard-Yale game? Check out the wide selection of neckwear (we suggest the "Harvard Sport" bow tie). Tailoring on-site, meanwhile, guarantees that your slacks will always have a break that's just so. 82 Mount Auburn St., Cambridge, MA 02138, jpressonline.com.
Tavi de la Rosa
Rare is the makeup artist who can shake you out of your routine with a single application of blush and eyeshadow. Tavi de la Rosa, who mans the Sisley counter at Neiman Marcus part-time and preps Boston's style icons, can suss out your look in minutes. For us, that meant smoky eyes, flawless foundation, and near-nude lips, plus a few false-eyelash applications for extra zing.
Brighter Lights Media
Ready for your silver-screen debut? Brighter Lights Media’s cinematic wedding-day videos document both the monumental moments and the intimate details in both short trailer and feature-film-length cuts. Bonus: Christian Nachtrieb and Chris Scesny’s stunning aerial shots, captured by quadcopter, let you watch your love story unfold from a birds’-eye view. 15 Channel Center St., Boston, MA brighterlightsmedia.com.
Uniform
Uniform owner Gary Ritacco has a keen understanding of what it means to balance personal style with form and function. His South End shop stocks timeless basics like fitted plaid and polka-dot button-ups and classic Levi’s alongside unexpected accessories that let your individuality shine through. Just imagine what a sleek Swiss messenger bag, a preppy Daniel Wellington watch, and ankle-high Tretorn sneakers could do for your weekend getup. 511 Tremont St., Boston, MA 02116, uniformboston.com.
Clear Flour Bread
In an era when everyone from your grandparents to your girlfriend has gone “gluten-free,” Clear Flour is unapologetically pro carb. Apricot-studded pain de seigle? Black-sesame sticks basted with garlic-herb butter? It’s easy to see why the yeasty, buttery scent of its long-fermented loaves continues to lure locals in droves. Just arrive early if you’re looking for something special (apologies to the woman behind us who wanted the last rosemary focaccia). 178 Thorndike St., Brookline, MA 02446, clearflourbread.com.
Brilliant Earth
Your relationship is conflict-free—shouldn't your ring be, too? The pros at Brilliant Earth go well beyond the industry standard, tracking diamonds from the time they leave the mine to the time they're cut and polished. A selection of fresh settings made from recycled metals and one-of-a-kind vintage looks, meanwhile, make it even easier to say yes. 38 Newbury St., Boston, MA 02116, brilliantearth.com.