The actress tours the cobblestone streets of Boston, looking effortlessly chic.
A straw fedora or wide-brim hat is so on-trend and the perfect finishing touch to any outfit. Bonus: It acts as an extra layer of SPF!
Sweater, $155, and shorts, $55, . Hat, $58, . Bag, French Connection, $68, . Ring, $100, . Shoes, $118, (20% off for orders of $50 or more with code GoodHousekeeping).
Sweet and breezy for hot August days, the peekaboo fabric is eye-catching on a flirty maxi dress, tops or even pumps!
Dress, $159, . Heels, Marc Fisher, $79, .
Located in Boston's industrial Seaport Innovation District, this sleek hotel has cozy rooms, a sexy rooftop lounge and waterfront views ideal for watching the sun sink into Boston Harbor.
Checks, please! The quintessential summer picnic print feels very now in fashion-forward pieces like a peplum top. Pair with cute fringed statement heels for a stylish alfresco lunch.
Top, $158, . Jeans, $45, . Sunglasses, Michael Kors, $159, . Bracelet, $45, . Heels, Ivanka Trump, $145, .
Say ciao to the best Italian sub in Boston (piled high with prosciutto, salami and more) at this family-owned sandwich heaven, located in the famous North End.
Fashion-y sneakers are the new flats. Totally metallic or accented with cheetah or colorful suede, they look super cool with everything from a dress to a summer suit.
Dress, $95, . Sweater, $70, . Earrings, $70, (enter for a chance to win a pair ). Sunglasses, Ray-Ban, $200, . Ring, $165, . Watch, $80, . Bag, $265, . Sneakers, $119, .
Climb aboard this schooner and sail Boston Harbor. The ship was modeled after a classic 1890s-style pilot schooner.
Dress outside the lines by pairing soft pastels like lilac and petal pink with more saturated primary picks.
Top, SJYP, $162, . Skirt, $95, . Sunglasses, $99, . Bag, $298, . Ring, $5, . Heels, Marc Fisher, $79, .
Wander down the streets of Boston's historic North End to sample some of the city's charm — and raved-about Italian restaurants like and .
Say goodbye to the baggy bibs of the '90s — the modern iteration is fitted, slim and slightly cropped above the ankle. Look for them in chic black, a dark denim wash or charcoal gray. And yes, wear with heels!
Overalls, $80, and shirt, $25, . Heels, $119, and bag, $198, . Sunglasses, $139, .
Sidle up to the DIY Bloody Mary Bar at this restaurant, then enjoy your creation — and take in killer city views — at the rooftop space.
Remember the prairie dress of the '80s? The flouncy silhouette is back and as floaty and elegant as ever. Pair with strappy heels and a shiny clutch to keep it out of Laura Ingalls territory.
Dress, $100, . Clutch, $25, . Ring, $85, . Heels, Steve Madden, $79, (20% off sitewide with code GHLULUS).
Cheers to summer — and unbeatable views of the harbor — at the Envoy Hotel's aptly named rooftop bar.
Opt for matching separates instead of a dress — you'll get more bang for your buck with pieces that are just as gorgeous apart as together. Savvy shopping for the win!
Top, $108, and skirt, $148, Eliza J, . Earrings, $65, (enter for a chance to win a pair ). Ring, $30, .
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This story originally appeared in the August 2016 issue of GolfHr.