In early September, Aaron and I took a long weekend getaway to Maine—our first without the kids. It might have been harder on me than them (thanks to my parents for spoiling them!). We spent two wonderful days in Kennebunkport, strolling through the historic town, browsing the charming shops, and enjoying fresh seafood.

While I love New England year-round, fall here feels especially magical. I left feeling refreshed, inspired, and ready to welcome the new season. In today’s post, I’m sharing what I wore on our trip, along with six preppy fall outfits to carry you through the season! But first, here are some photos I took from our trip!

Preppy Fall Outfits I Wore In Maine

Now, let’s dive into the looks! We had just one full day in Kennebunkport, as we were attending a friend’s wedding about an hour away on Saturday. To start the day, we grabbed breakfast at a charming little café called Mornings In Paris. The sandwiches and fresh coffee were delicious, and it dawned on me that it was the first time I’d gone out for breakfast in years—it felt like such a treat!

Look 1: Shopping Around Kennebunkport

The morning was cooler than expected (no complaints here!), so I opted for jeans, my Tretorn sneakers, and the Emilie lady jacket from J.Crew. Underneath, I wore my favorite everyday tee, and as the afternoon warmed up, I casually draped my sweater over my shoulders. Naturally, I couldn’t leave without my trusty boat and tote in hand!

Strolling Around Town Look – OUTFIT DETAILS: Top / Striped Cardigan / Similar Jeans / Bag / Sunglasses

Look 2: Dinner & A Stroll

After an afternoon of shopping, we returned to our charming beach cottage to get ready for dinner. That evening, we dined at Mabel’s Lobster Claw and, of course, had another lobster roll. For dinner, I chose to wear my J.Crew barn coat (I’ve linked a similar one from L.L.Bean below!), paired with my go-to striped top, jeans, and leather flats. This look was a great preppy fall outfit for a cool evening.

Afterward, we took a stroll around Walker’s Point, enjoyed some ice cream, and headed back to the cottage to watch Harry Potter!

Dinner Look – OUTFIT DETAILS: Similar Barn Coat / Striped Top / Jeans / Bag / Flats / Belt

Look 3: Fall Outdoor Wedding

Saturday morning began with a quick stop at H.B. Provisions for a bite before we strolled around town one last time, soaking in its historic and quaint charm.

Soon after, we headed north for our friend’s wedding at the historic 1774 Inn in Phippsburg, Maine. Nestled by the river, the venue offered breathtaking views that perfectly captured the beauty of the season. I wore a Tuckernuck dress, and I couldn’t have made a better choice—it was ideal for an outdoor fall wedding!

OUTFIT DETAILS: Dress / Similar Shoes

Finally, on Sunday morning, we headed back home to Pennsylvania. And while it was so good to have a little getaway, I was so excited to go home and hug Teddy and Kit!

Feeling Inspired: Preppy Fall Outfits

New England holds a special place in my heart. With Aaron being from the Boston area, we spent countless days there during our dating years. And it has always been a major source of style inspiration for me.

The region’s preppy and classic aesthetic, deeply rooted in Ivy League traditions, sailing, and country clubs, exudes a timeless elegance. Being back in a charming coastal town filled me with fresh inspiration and excitement.

So, I couldn’t resist creating a few preppy fall outfits, perfect for your next New England getaway—or wherever fall takes you. Here are six preppy fall outfits for you: