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.
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.
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.
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, .
From the moment Jessica Thornton asks her first question—"What do you want your hair to say about you?"—it's clear she genuinely wants you to love your locks. The stylist leaves hair so perfectly voluminous that some of her regulars can't resist visiting her one-woman shop for a blowout ($85) multiple times a week. 40 River St., Boston, MA 02114, greenroomboston.com.
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 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.
With a growing list of celebrity attendees and a painstakingly selected roster of movies each year, IFFBoston is your best chance, and sometimes your only chance, to see rare indie movies at theaters across the city. Sometimes it’s a big name trying something new; other times it’s a breakout film from a new director. Either way, it’s comforting to know that big screens aren’t just for Avengers movies. iffboston.org.
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.
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.
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.
After tasting every cake in town—hey, anything for the job—it's official: Party Favors' sinfully rich but not-too-sweet cake/frosting combo is the most delectable. You can mix and match colors and flavors for filling and icing, and sample two combinations before making a decision. Bring in a wedding photo of your cake a year later, and the shop will make you a mini anniversary replica for free—a handy service, considering your reception guests will want to devour every last morsel of the original. 1356 Beacon St., Brookline, MA partyfavorsbrookline.com.
A wedding gown is more costly than anything else in your closet. Why buy it off the rack when you can get a couture creation? Designer Hernández will build the dress of your dreams from scratch. Simply walk upstairs to her lovely studio and collaborate with her to produce a dress the likes of which you literally won't see anywhere else. 165 Newbury St., Boston, MA .
After you're done drooling over Audio Concepts' fantasy home-theater setups—massive TVs, booming speakers, George Jetson-worthy remote controls—find a salesperson and tell him your audio-visual dream. No matter the budget, be it $1,000 or $20,000, he'll briskly and breezily sketch out a plan to turn your underutilized family room or basement into the neighborhood cinema. 870 Commonwealth Ave., Boston, MA audioconcepts.com.
Get personalized attention every step of the way at Marathon, where sharp-eyed employees will diagnose your stride on the sales floor and then bring out model after model in search of the right fit. (Customers are encouraged to take a test jog outdoors, too.) Be it Mizuno, Saucony, or other elite running shoe, your purchase is guaranteed to be ready for action—from a 5K to a stroll at the dog park—right out of the box. 671 Boylston St., Brookline, MA 2445, marathonsports.com.