Summertime: Boston Events & City Looks You Have to Try

Summertime, it’s a song, a season. It’s youth at any age. It’s longer days, shorter nights. It’s romance, a reminisce. It’s a rooftop, an island. It’s true of all things wonderful… it always seems too short.


Summers in the city are perfect for our hyperactive generation because there’s always something to do, knowing when and where these events take place is key! If you’re tired of the clichés that pop up on google search engine when looking for something to do, then check out some of these unconventional ideas and events to try out this summer along with some of our favorite summer in the city looks!


Art Festivals:  Boston is like falling through a rabbit hole into a melting pot populated by pulsating art, history and culture. The art scene is one that draws millions to this city with famous galleries, impeccable architecture, and masterpieces of all kinds. Endure these scenes in unconventional ways this summer like art festivals. They range from sand sculptures at the Revere Beach Sand Sculpting Festival, stand-up acts at the Comedy Arts Festival, performing arts at the Boston Summer Arts weekend, physical art at Boston Arts Walk and more.



This super trendy jumper is the perfect summer outfit for any occasion really, but what outfit for an arts festival then one that screams creative free-spirit? An easy outfit to pair so you can make the most of running through that summer breeze and floral fields.



Boston Calling:  Look, if you had one shot, one opportunity..

Would you miss an Eminem performance? Boston Calling is a three-day music festival that features the best acts in music and comedy as well as visual arts- it’s the Coachella of the east side… represent. The range of music is what makes it a festival for all, from rap performances like Eminem, to rock performances like the Killers, and from soul music like Daniel Ceasar… you can’t beat the variety of entertainment. Boston Calling will be taking place at the Harvard Athletic Complex on May 25-27, but don’t forget to purchase those tickets in advance!



Bodysuits and denim skirts make for a cool and casual look when rocking out those summer nights. It’s been awhile since we’ve seen these skirts strutting the streets but after seeing the new styles that stole the spotlight I think all of our original skepticism of this new trend has faded out. Throw on a pair of trendy sneaks to complete a killer and totally reasonable concert outfit this summer!


Sky-lit Skyline Dinner Views: It’s the city my friends, if you haven’t experienced dinner with a view already then do you even eat? Check out the Harborwalk Terrace for waterfront bites, cocktails and stunning views of the harbor. They host musically themed evenings at 6pm every Tuesday through Thursday like pop soul, rat pack, blues and more! Nothing says authentic Boston like Frank Sinatra tingling the soul while sipping on some taxed wine by the city-lit harbor.



Sultry slips are a go-to for those summer nights whether you’re on a date or having a night out with the girls. Summer has no rules, including color rules… you can go with the subtle sweet pea pinks or the darkest of little black dresses and slay whichever way the color wheel turns.



Outdoor Movies: Switch up your movie theatre experience this summer to outdoor, where the Boston Harbor Hotel at Rows Wharf and the Hatch Shell offer free movies every Friday! It’s like living a movie scene except unlike Eternal Sunshine of the Spotless Mind you’ll be laying under the stars in warmth, cause…. SUMMER.


Switch up the denim for these other high-waisted short options that are a classic for dressing up or keeping casual. Not sure when you’re gonna wear the simple white staple top that sits in your closet? Let your shorts do all the talking! Mix up your short game with bow-ties and stripes and create your outfit from bottom-up.



Picnics & Pop Ups: Picture perfect weather calls for gingham blankets and woven baskets filled with an assortment of cheeses and a bottle of bubbly, am I right!? Luckily in Boston there are plenty of beautiful spots to picnic like the Arnold Arboretum, Esplanade, Boston Common, Fitzgerald Greenway and more! But look out for events that will take place at these postcard sceneries if you wanna take your picnic game to the next level, like pop up drinkeries! Yes, there will be a Downeast Cider drinkery pop up taking place at the Rose-Fitzgerald Greenway said to run from late May through October! Food trucks, lawn games, live music, and all the summer vibes you’re looking for.



We love the long-legged jumpsuits for those city summer days and nights that take you from picnics in the day to painting the city red at night. It’s the perfect soft, comfortable fit when lounging around in the green fields, not to mention waist ties that compliment your flattering silhouette at the same time.



Urban Beach Bum: Being an urban beach bum isn’t all too different than islands in the Caribbean, right? All you need is sand, the big blue sea, and a piña colada in hand. Some places in Massachusetts are unreal in terms of natures beauty and beaches, but there are still city options for those car-restricted city-living citizens. Head to South Boston with your beach towels and sun shades to catch rays looking out onto Dorchester Bay. Catch one fish, two fish. Red fish, blue fish. At one beach, two beach. Either L Street, M Street.



Maxi wrap skirts are all the island tings you need blowing through the breeze. And matching your maxi to your swimsuit?! Now that is the definition of an urban beach bum. Who said you can’t make a style statement while those sandy cheeks catch the summer rays.

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