Fall Fashion I’m Loving | Classic New England Style at L.L.Bean

I went to L.L.Bean for a little fall clothes shopping. Today I’m sharing some of the styles I’m loving this fall, what I tried on, and what came home with me.

Hello, friends. Here we are on the other side of Labor Day. While I usually continue (stubbornly, optimistically) to hang onto summer until the autumnal equinox later this month, I have to admit that this week felt like a decisive step into fall.

So, though I’m not yet ready to embrace the new season in my home, I have, out of necessity, started to pull warmer clothes from my closet, swapping shorts and light tops for jeans and cozy sweatshirts.

And it has me thinking about fall fashion, a topic that always evokes feelings of both nostalgia and anticipation — memories of shopping for that all-important first-day-of-school outfit (usually, since I didn’t grow up in Maine, something too warm for the still summer-like weather) and hours spent paging through the thick fashion tomes that used to hit newsstands in late August.

These days, instead of print, I keep my eye on social media and favorite brand sites to see what styles are having a moment. I have already made some online purchases (mostly resale items from Poshmark), and of course I have a closet full of clothes, but last weekend I thought it would be fun to take a drive down to the L.L. Bean flagship store in Freeport to do a bit of in-person shopping.

Today I’m sharing some of the styles I’m loving this fall, what I tried on at L.L. Bean, and what came home with me.

This is definitely something a little different for me, but are you ready for a fashion show?!

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The Fall Styles I’m Loving This Year

First, let’s talk about the fall styles I’m loving this year.

I have been a New England girl at heart since my college days, and, happily, one in real life for the past 10 years. So those cozy Ralph Lauren-style fall montages that keep popping up in my Instagram feed are exactly how I think the season should look and feel.

I’m talking all the classics: plaids and crisp stripes, with a sweet floral thrown into the mix. Flannel, corduroy, and wool tweed. Rugged utility pants and jeans. Cable-knit sweaters, collared knits, and already-broken-in sweatshirts. Denim shirts and barn jackets.

And a few twists to keep things lively — trouser or barrel-leg jeans, pull-on pants (maybe in a silky fabric!), and ladylike silhouettes. All in shades of blue, brown, burgundy, camel, and olive. And on the feet, moccasins, loafers, suede sneaks, and Bean boots.

These pieces layer together happily for a wearable look that signals warmth, comfort, practicality, and ease, with enough tailoring to keep it from becoming sloppy.

Exactly the kinds of clothes I want to wear this fall.

LL Bean

They are also styles that L.L. Bean has been selling for years.

If, somehow, you are not familiar with this iconic Maine institution, let me fill you in quickly. Established in 1911 by Leon Leonwood Bean to market his original-design waterproof hunting boot, LL Bean has grown and diversified through the years and now sells everything from hunting, fishing, and outdoor gear to casual clothing, accessories, and shoes, to furniture, tableware, bedding, and rugs. They embody good old-fashioned Yankee style — tailored, no-nonsense, and timeless.

Back in 2025 I wrote a post about L.L. Bean, its Freeport “campus” made up of five different stores, its history, and extensive partnerships in the community. You can read it here.

At that time, L.L. Bean had just started a major renovation of its flagship store. Construction is almost done now — the grand opening celebrations kick off September 18-20, followed by five more weekends filled with special events.

If you are in Maine to peep the fall foliage, be sure to check out the schedule here. Or at least stop by Freeport to visit the new store. I can’t wait to see it!

What I Tried On and What Came Home With Me

Last weekend the women’s, men’s, and children’s clothing was still located in the enormous 28,000 square foot tent-like structure that was erected in a parking lot during construction. The racks were full and the displays were on point, but I was told that the new store is already stocked with new fall merchandise, some not available in “Camp LL Bean”. Disappointing!

Still, I filled my arms with clothes and made my way to the dressing room.

I have to admit I felt fairly foolish taking “fit pics” (especially being a woman “of a certain age”). The lighting and angle in the dressing room were terrible, so I marched out in each outfit to a full-length mirror in the nearby rain jacket section. I kept explaining to people that I was writing a blog, though I don’t know if that made me seem more or less ridiculous.

But, for you, my readers, I will do (almost) anything.

I tried on seven different tops and four bottoms. Here are the outfits I styled with them.

Fisherman sweater + Trouser Jeans

I immediately fell in love with this take on a fisherman sweater with its quarter-button placket and stand-up collar. So many style moments in one piece. It is a soft cotton in a thick knit. I also liked the shorter length, perfect with more relaxed bottoms.

I paired it with wide-leg trouser jeans — comfortable enough to wear every day, but with a bit of extra polish. Since I am long-waisted and around 5′ 4″, I went with the petite length. They hit just above my ankle bone, which was perfect. I find that longer wide-leg pants can overwhelm my frame.

Underneath, a tailored dark chambray shirt. You’ll see this shirt make an appearance in multiple outfits. It or a medium-wash denim shirt are a great wardrobe staple. The denim shirt I had seen in the catalog must have been hidden away in the new store.

Rugby shirt + Utility-style Jeans

I have been seeing rugby shirts everywhere for fall. You know how I love a stripe, so of course I had to try on this collared version. I sized up for a slouchy fit and styled it over the chambray shirt for a layered look. It would look great paired on its own with sweats too for a comfy day at home.

On the bottom, a pair of utility jeans with wide legs and front pockets. This is another fun and different style of denim. These are a nice lightweight fabric for this time of year. They ran a bit shorter than the trouser jeans, so I tried the regular length.

Burgundy Rugby Shirt

Of course I went for the navy and white striped rugby first, but I think I like this burgundy version even better. It is such a great color for fall.

Paired here with the chambray shirt and trouser jeans.

Flannel Popover

Living in Maine, I of course have many plaid flannel shirts. This slightly cropped, collarless popover style, though, is a more feminine take on the classic, It is made from midweight, softly brushed yarn-dyed fabric with a slub texture. I also love the bold buffalo check pattern. I sized down for a tailored fit.

Canvas Pants

During the cooler months I wear jeans most days. They pair so easily with pretty much everything. But I am trying to incorporate more non-jean pants into my wardrobe. These high-rise wide-leg canvas pants would be a versatile addition. L.L. Bean has the same style in corduroy, but they too must have been hidden away in the new store. There is a pair on sale on their website in a fun bright blue that I have my eye on.

I grabbed this cute striped polo shirt to try on with the pants. Not sure if it is exactly my style…

Cotton-Cashmere Polo Sweater

Collared sweaters are having a moment right now, so I tried this lightweight version. It was fine and would pair nicely with some patterned pants for added interest. I think the more classic polo style I saw online, with buttons, would be more up my alley.

Y-Neck Flannel Shirt + Barrel-Leg Jeans

This Y-neck flannel shirt is another fresh take on the usual flannel shirt. I loved the popover style with a pert little collar that stood nicely at attention. The open neckline framed the face nicely. I loved everything about this shirt except the colors. This indigo tartan was the best on me, but I wouldn’t call it great.

I have several pairs of barrel-leg pants and I love the relaxed cut. I also think, if the barrel isn’t too pronounced, they can be very flattering. If you haven’t tried them, you should!

Shoes and Accessories

The shoes and Boat and Totes are temporarily housed in the Hunting and Fishing store. I made a brief stop there on my way to the big tent and quickly slid a foot into a mule-style boat shoe/moccasin. I wish they came in colors other than shades of brown, maybe blue or black? Do you hear me, L.L. Bean?

There is a slip-on rubber moc Bean boot that does come in blue, however, which would be great for our snowy/wet/muddy weather. You can never have too many boots when you live in Maine. I added it to my list.

And, of course, you also must have a Bean Boat and Tote, whether you live in Maine or not. Go for the original or one of the new styles such as the crossbody (the black would be perfect for fall). And be sure to get something fun embroidered on it.

I was lucky to find a perfectly broken-in 1970s “Bean bag” at a local vintage sale last year, which I use as a purse in the summer. They can cost a pretty penny these days (mine was a relative steal), but they have a style that can’t be replicated. Look for them on Poshmark, eBay or Etsy. As part of its grand reopening, L.L. Bean is hosting a vintage product drop, including bags, September 25-27 exclusively at its new Freeport store.

What Came home with Me

So, can you guess what came home with me?

There weren’t any real losers in all that I tried on. And I was tempted by a number of items. In the end, though, there were three standouts for me.

I couldn’t leave without the blue buffalo check flannel, the trouser jeans, and the fisherman sweater.

Did you guess right?!

For the record, I ended up ordering a denim shirt and a rugby shirt from Poshmark. I will share them another time!

Shop My L.L. Bean Fall Finds

Shop the individual items below, or browse all my L.L.Bean fall finds in one place.

This Week Into Next

With cooler weather and meetings of both the AIO Board and Lighthouse Committee, this really has felt like “back to school” week after summer vacation.

And, truth be told, I had a lot weighing on my heart and mind this week — aging pets (Cisco and Tuck have both been “off”) and the 25th anniversary of the 9/11 attacks.

So this post on fall fashion was a fun distraction. I hope you enjoyed it too.

I have also tried to give myself grace in other ways — a rainy morning spent finishing a book under a blanket on the couch and the U.S. Open tennis matches at night. And, of course, always, always moving my body with Peloton.

This weekend I am meeting up with friends on both Saturday and Sunday, so that will be nice too.

Next week I am planning to go to the Montsweag flea market early on Wednesday morning. I hope to share it with you on Saturday.

That’s it, friends.

Be well, and be kind.