Packing List: Summer Weekend In Boston

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Boston and I are quite familiar acquaintances.

I went to college in Boston. My sophomore year, I arrived early to work on an Emerson College TV program for incoming freshmen to get to know the city. My first thought while lugging my stuff up Tremont Street was, “Damn, it is HUMID.”

Boston summers, you do not play.

Boston In Summer: Outfit Inspo For A Weekend Trip

Boston is such a fun city to explore as long as you’re prepared for its occasional temperamental weather. From cannoli’s at Mike’s Pastry in the North End, shopping on Newbury Street, walking the Freedom Trail, and drinking a Sam Adams across from his grave to eating dim sum in Chinatown, watching a ball game at Fenway, strolling through the Boston Public Gardens with a fresh iced Dunkin’ in your hand, and day tripping to the Cape (hop on the Plymouth-Brockton and be in Barnstable in less than an hour!), there are endless activities for people of all ages in Beantown.

The key to making it enjoyable is knowing how to pack.

So, I dug way back into my memory and schmoozed with some old friends still living in Boston to create the ultimate summer packing list for a jaunt to The City on the Hill.

The key to making a summer weekend in Boston enjoyable is knowing what to wear. Thus, the ultimate packing list for a jaunt to The City on the Hill.

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1| Boston Sweatshirt

A cute, slouchy sweatshirt is a must for layering in Boston weather.
Image Credit: Etsty

I know a sweatshirt in the summer may seem counterintuitive, but you’ll wish you had one when it’s overcast and 50 degrees in the morning. Boston weather is unpredictable, so a cute, slouchy sweatshirt (especially one espousing the hometown) is a must. Layering is the theme of this packing list. Lots of layers.


2| English Factory Elastic Detail Sleeveless Dress

An easy, breezy dress from English Factory is clutch when you're traveling over the summer.
Image Credit: Shopbop

Iterations of the faux taco dress continue to flourish — including this darling white number from English Factory. An easy, breezy dress is clutch when you’re traveling over the summer, especially for a night out on the town (may I suggest Contessa at The Newbury or Troquet at 107 South St. for a delicious meal). If you’d prefer a dress with sleeves, check out this similar option from WAYF.


3| Madewell Broken-In Baseball Cap

This broken-in baseball cap from Madewell is cute, sport & perfect for walking.
Image Credit: Madewell

If you’re not going to wear a Red Sox baseball cap, I strongly encourage an innocuous cap like this broken-in baseball cap from Madewell. It comes in a ton of colors, but I’m partial to the light pink. Cute, sporty, and perfect for walking the cobblestone streets of Beacon Hill!


4| Fujifilm Instax Mini 11 Instant Camera

Use an Instant Camera to snap a pic of historical spots.
Image Credit: Urban Outfitters

There’s a ton of picturesque/historical spots to snap a pic, why not use an Instant Camera for photos that have that throwback feel? We have one of these that we used on a trip to New Mexico and my daughters LOVED it. Perfect for scrapbooking!


5 | J.Crew Perfect-Fit Shelf-Bra Tank Top

J.Crew's Perfect-Fit Shelf-Bra Tank with a built-in bra could be layered under a button-down shirt or duster.
Image Credit: J.Crew

I don’t know about y’all, but I hate wearing a bra in the summer. Just extra garments that feel icky especially if you’ve been galavanting all day around a city known for its summer humidity. J.Crew’s Perfect-Fit Shelf-Bra Tank is a top that looks good on its own, but could also be layered under a button-down shirt or duster. I also love that it has a built-in bra. Sweaty kid’s dream!


6 | Madewell’s The Perfect Vintage Military Short

These Madewell Perfect Vintage Military Shorts are casual, but preppier and a little more put together (perfect for Boston).
Image Credit: Madewell

I love a pair of jean shorts as much as the next mama, but there’s something about these Madewell Perfect Vintage Military Shorts that are calling my name. They are casual, but a little more put together. And a bit preppier (which works in a town like Boston).


7 | QUAY Noosa Cat Eye Sunglasses

A pair of classic cat eye sunnies that are fun and fresh for summer, but also won't break the bank.
Image Credit: Nordstrom

A classic cat eye sunny with a twist. I adore the color of these Quay Noosa Cat Eye Sunglasses. They are fun and fresh for summer, but also won’t break the bank. There is nothing worse than losing designer sunglasses on vacation.


8 | Veja Urca Sneakers

These Veja sneakers are timeless, adorable & eco-friendly! This pair will go with everything + are perfect if you don't want blisters from a long day of walking.
Image Credit: Shopbop

I am DYING to try a pair of Veja sneakers. They are timeless, adorable and eco-friendly! This pair will go with everything and you can pick up the pink in other areas of your outfit. Boston is definitely a walking/public transportation kind of city. If you don’t want blisters after the first day, definitely pack a solid pair of sneakers.


9 | Norma Kamali Bishop One-Piece Swimsuit

I adore the color of this strapless Norma Kamali swimsuit. It's stunning in its simplicity.
Image Credit: Zappos

I never travel in the summer without a swimsuit. Whether it’s a hot tub opportunity or a day trip to the Cape, having a swimsuit on hand is clutch. I adore the color of this strapless Norma Kamali swimsuit. It’s stunning in its simplicity. If you prefer straps, this J.Crew Ruffled One-Piece is a great bet.


10 | GAP Linen Boyfriend Shirt

This Linen Boyfriend Shirt from GAP  looks great layered. Linen is nice & lightweight, which is ideal for a little more coverage.
Image Credit: Gap

I love the versatility of an oversized shirt. This Linen Boyfriend Shirt from GAP would look great layered over the J.Crew tank and Madewell shorts, or as a cover-up for a bathing suit. Linen is nice and lightweight, which is ideal if you want to be a little more covered up, but still cool.


11 | Madewell Herringbone Chain Necklace

This Herringbone Necklace from Madewell goes with everything & makes me feel a little more put together.
Image Credit: Madewell

I typically do not travel with a ton of jewelry (although when I do, I use a case for storage similar to this one to keep everything untangled). I usually wear the same earrings and pack a necklace, like this Herringbone Necklace from Madewell, that goes with everything. Something just makes me feel a little more put together when I have on a smidge of jewelry.


12 | Clare V. Fanny Pack

Nothing is better than being hands-free when exploring a new city. The Clare V. Fanny Pack is classic, functional and on-trend.
Image Credit: Shopbop

Fanny packs are back and I am HERE for it. Nothing is better than being hands-free when exploring a new city. The Clare V. Fanny Pack is classic, functional and on-trend.


13 |lse Jacobsen Raincoat

Have the Ilse Jacobsen Raincoat in the Adobe Rose color in hand just in case.
Image Credit: Nordstrom

There’s not a “rainy reason” per-say in Boston, but it’s always good to have a raincoat on hand just in case. I love the color of this Ilse Jacobsen Raincoat, definitely not your typical yellow slicker!


14| Mini Windproof Folding Travel Umbrella

Bring a mini travel umbrella with a cute little case to pack light on the trip.
Image Credit: Amazon

If you’d prefer to pack light, throw this mini travel umbrella in your carry-on! It comes in a ton of colors and I love that it has a cute little case to store it.


15| Sam Edelman Inara Slide Sandal

These stylish Sam Edelman Inara Slide Sandals are great for a night out.
Image Credit: Nordstrom

You’ll want a stylish pair of sandals for a night out (trust me, save the stilettos for a city without cobblestones), these Sam Edelman Inara Slide Sandals certainly fit the bill. If you prefer heels, check these block heel sandals out.

I realize I made Boston sound like some swamp dystopia, but I promise if you pack right you won’t feel the need to throw yourself in the Boston Harbor like a chest of English tea. Light layers, the correct shoes and some travel accessories and you’ll have a wicked good time.

Now for a quick trip down memory lane…

The key to making a summer weekend in Boston enjoyable is knowing what to wear. Thus, the ultimate packing list for a jaunt to The City on the Hill.
No I didn’t go to college in the ’50s. I competed in a lot of Speech & Debate on the weekends. As you do.
The key to making a summer weekend in Boston enjoyable is knowing what to wear. Thus, the ultimate packing list for a jaunt to The City on the Hill.
I was SO blond my Junior Year. A choice, among with all the strapless tops and long necklaces LOL.

x, Meredith