If you love classic, timeless fall style, you’re in the right place — I’m sharing 9 preppy fall outfits, from what I actually wore on a New England getaway to six looks you can recreate anywhere this season.
If there’s one season that was made for classic, preppy style, it’s fall — and I’m sharing nine of my favorite preppy fall outfits today, from what I actually wore on a New England getaway to six timeless looks you can recreate wherever autumn takes you. 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!
What to Wear: Preppy Fall Outfits for Every Occasion
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!
Classic Preppy Fall Outfit Ideas
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:
Bean Boots / Barbour Jacket / Boat & Tote Bag / Duck Sweater / Pearl Earrings / Jeans / Socks / Aviators
Riding Boots / Vest / Cream Ribbed Turtleneck / Pearl Earrings / Skinny Jeans / Aviators / Plaid bow / Horsebit Belt
Love These Preppy Fall Outfits? Check out my Classic Fall Capsule Wardrobe!
Mules / Navy Corduroy Pants / White Blouse / Patterned Vest / Watch / Purse / Earrings / Sunglasses
Boots / Jeans / Plaid Coat / Brown Leather Purse / Earrings / Brown Turtleneck / Watch / Sunglasses / Brown Bow
Green Corduroy Skirt / Patterned Vest / White Blouse / Bag / Boots / Bow / Earrings
Boots / Bag / Sweater / Jeans / Gold Bracelet / Trench Coat / Gold Earrings / Brown Bow
Frequently Asked Questions About Preppy Fall Style
What are the key pieces in a preppy fall wardrobe?
A classic preppy fall wardrobe starts with a few reliable workhorses: a well-fitted blazer or lady jacket, straight-leg or slim jeans, a striped top, a cable knit sweater, and a versatile outerwear piece like a barn coat or trench. Layer in riding boots or loafers, and you have the foundation for almost any preppy fall outfit. These are the pieces I come back to every single year.
How do I style preppy outfits for fall without looking too formal?
The key is in the layering and the footwear. Pair a structured blazer with your favorite worn-in jeans and sneakers to keep it casual, or swap leather flats for ankle boots to add just enough polish. Preppy fall style is at its best when it feels effortless — think put-together, not overdressed. A sweater draped over the shoulders never hurts either.
What shoes work best with preppy fall outfits?
Loafers, riding boots, leather flats, and classic sneakers like Tretorns are the most versatile options for a preppy fall wardrobe. Bean boots are a New England staple that earn their place the moment the weather turns. The goal is footwear that feels grounded and classic — nothing too trendy, nothing too precious to actually wear.
What’s the difference between preppy style and classic style?
Preppy style is a subset of classic style — it draws specifically from Ivy League, sailing, and New England traditions, and tends to lean into details like Breton stripes, plaid, pearl earrings, and heritage brands like J.Crew, L.L.Bean, and Barbour. Classic style is a broader category built on timeless, versatile pieces that transcend any single aesthetic. On this blog, they overlap almost entirely — because the pieces that define preppy style also happen to be the most enduring ones in any wardrobe.
I hope you love these preppy fall outfits! As always, come say hi over Instagram! All my looks can be found on my LTK, and my ShopMy.
xoxo,
Brooke
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