I first traveled to New England in Fall 2019 when I went on a cruise with Seabourn. The area is so beautiful, the weather just perfect in late summer and fall and, of course, the history! I was really excited to head back to Boston and Cape Cod for my friend’s bachelorette party. For this trip, I did not want to overpack and bring things I wouldn’t even get to wear. Since we had a good itinerary laid out, I’m going to share what to pack you’ll actually wear for a Cape Cod Bachelorette weekend in late Summer! I’ll admit, as someone who loves to wear white year-round, for the months leading up to this I made a conscious effort to get non-white clothing!

The most talked-about item before and during the bachelorette was these babe and bride swimsuits! Not everyone was a fan, but we all love our bride and this weekend is all about her and what makes her happy! When it comes to a wedding if the bride and groom say, “Jump” you should ask, “how high?” I actually don’t think these swimsuits are that bad, but I can understand why some may not like them. We got black for all the bridesmaids since the consensus was those would be the most flattering for everyone. I got size small and it fits well with a high-leg cut.

Dresses

I am a huge fan of a dress on trips. It’s one simple piece and you’re done. You don’t have to worry about mixing and matching. For this Cape Cod Bachelorette weekend, two of my dresses pulled double duty as swimsuit coverups. Now, were they a bit “much” as coverups? Yes, but they were perfect for going from the beach to a nice meal and everything in between!

I brought a black mock-neck sweater dress for our first dinner together in Boston. This was one of the times where the bride specified she wanted us all to wear black! I love how this dress is great for workwear but fun enough for dinner and a cocktail party!

The next two dresses I brought were what acted as swimsuit coverups. You can use code HKCUNG15 to get 15% off the site! I love this gingham dress because it’s linen and lightweight. In case I needed something slightly more formal, this midi dress worked out perfectly. Both dresses come in a couple of colors! I got size 2 in both, which is the smallest size available.

Shop my full gingham dress look here and the midi dress look here.

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Separates

When packing for a trip I always think of items I can wear multiple times. You can’t really see it on the boat photo, but this mock neck sweatshirt saved me so many times! When we first got to Whitecrest Beach it was so cold before we walked down the steep dune to get to the beach. Not to mention, our picturesque sunset sail was freezing, so this sweatshirt really came in handy with my favorite Mom jeans.

Other separates I packed, but didn’t get a chance to photograph include a fun sheer sleeve blouse (HKCUNG15 for 15% off) for dinner, sweater tank and plaid blazer. On the way home, I wore my favorite joggers with the sweatshirt to stay warm on the plane.

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Accessories

In an effort to keep things simple this Cape Cod Bachelorette weekend, I packed three pairs of shoes, including the pair I wore on the plane. A pair of block heels for both casual and dressy outfits, sandals for the beach and loafers for the plane.

Travel Musthaves

I didn’t bring a full size luggage this trip and instead used my Bric’s carry-on! It rolls like a dream and I love how the compartments are divided. I use these packing cubes to keep things organized. As usual, I brought my Tumi leather backpack for my laptop and a makeup bag.