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The Ultimate Packing List for New England Summer Travel

I’ve said it before and I’ll say it again, I love planning – and packing – for a trip.  Almost as much as the trip itself! It’s so fun to curate a packing list for a destination that has a strong sense of place while also maintaining a timeless appeal. Now that we live in New England it’s easier than ever to  lean into a classic all American aesthetic when packing for our first trip of the summer to Nantucket, Newport and Martha’s Vineyard. 

So here is what I packed for a week-long getaway in the New England and you can see how I’ve styled these pieces in my daily looks

New England Vacation Packing List: 

Dresses: In the summertime I love a throw-on-and-go outfit and adore the effortless appeal of this shirtdress (blue version here), this striped maxi and a preppy tunic dress

Tops: This cable knit tank has been my favorite piece so far this summer (worn here, here, and here!) and is only $55. And it doesn’t get more classic than a linen shirt with the perfect proportions to tie at the waist. 

Sweaters: Coastal areas are known for chilling mornings so I brought a lot of sweaters, including this iconic flag sweater, a nantucket red crewneck (purchased from Murray’s Toggery on ACK), this ivory cashmere v-neck and this amazing blue and white wrap cardigan

Jackets: You only need a little jean jacket in the summer.

Pants: A great pair of white jeans are a summer essential (size up) and these patterned silk trousers are so special I wore them multiple times on the trip. 

Shorts: I love a good shorts + sweater combo on vacation and packed this preppy plaid pair, these classic 4″ white chino shorts (plus the nantucket red version) and a navy tailored pair (only available in J.McLaughlin stores, but love these too!) 

Skirt: Molly Moorkamp can do no wrong in my book and I love her tiered linen Topsy skirt (sadly it’s from last summer but this is similar!) 

Shoes: There are always several pairs of Sarah Flints in my bag due to their wear-all-day comfort perfect for days spent exploring. This time I packed these white 60mm block heels, these mirjana slides and these grecian “grear” sandals. I also brought a pair of Stubbs and Wootton Loafers, nautical flip flops and these classic navy Jacks

Hats: Peter Beaton’s Galley Beach XXL hat is perfect for saving your skin from the sun’s rays, and I love this bucket hat that truly lives up to it’s name. Plus I always have a baseball cap in my bag for early morning coffee runs. 

Luggage: I’ve been carrying Paravel’s grand tour duffle for 3 years and it still looks so good! 

Bags: Somehow I went overboard on bags for this trip and ended up with eight (!?) aside from my luggage including:  this clutch, this navy wicker bag, this striped “lunchpail” bag, a large straw tote perfect for the beach and only $34!, a gingham tote, a box bag (old, similar here), a classic l.l.bean boat and tote, and a crescent basket bag (old but this is similar). I’m not sure what happened but generally advise keeping it to 3-4 bags max (especially when they can be packed inside each other!) 

Beach wear: I bring this white tank bathing suit on almost every trip as it presents countless styling options. This gingham one piece is another go-to and super flattering. Either suit pairs with a tunic (mine is old but love these) or my favorite patterned pareos

Active wear: I usually do a Peloton mat work out in my pajamas when traveling, but picked up THE CUTEST tennis set at the J.McLaughlin store in Edgartown (tennis skirt, and zip jacket) and Steph got the same set in navy. 

Accessories: Aside from an absurd number of bags, my accessories were very simple: a tan cashmere wrap for the ferry, these pearl studs, a pair of tortoise sunnies (only $23 right now!!) and these sand colored sunglasses I bought at the “general store” at Winnetu to twin with Steph. 


More Vacation Favorites: 

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  1. Allison S. Henderson
    June 7, 2022 / 10:29 pm

    All you summer pieces are such classics. Just love them all.

  2. Jeff Laskowski
    June 8, 2022 / 8:34 pm

    I always look forward to seeing your timeless and classic ensembles. You always look impeccably stylish and perfectly comfortable.

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