Fall Fashion Trends with Staying Power: Timeless Pieces Worth Investing In
Every fall, the trend reports start rolling in, but I’ve noticed that many of these so-called “trends” are really timeless styles that just make their seasonal comeback. The colors or little details might change, but the core pieces stay the same and can anchor a wardrobe for years. That’s why I love this season for making smart, long-term wardrobe investments. Today I’m sharing a few of my favorite fall fashion “trends” that never go out of style.
And I’m joining up with some of my blogger friends to share our takes on Fall Fashion.
Most Lovely Things | Classic Casual Home | Cindy Hattersley Design | La Vie On Grand
Timeless Fall Fashion “Trends”
This fall, “heritage dressing” is having a moment: plaid, Fair Isle, blazers, loafers, silk scarves. But honestly, you could just as easily call it Preppy or Classic. These styles show up on the “trend” lists every year or two, but I don’t think of them as trendy at all. They’re more like the comfort food of fashion…familiar, reliable, and easy to return to when the world feels a little uncertain. And because they always come back around, these are the kinds of pieces worth investing in for the long haul.
Style tip: Unless your Style Personality is straight-up Classic, I think “heritage” pieces look best when mixed with more contemporary and/or personality pieces. Otherwise the look can skew a bit costume-y.
How to Wear Plaid for Fall (Without Looking Trendy or Dated)
Plaid is one of this fall’s fashion “trends” that’s truly a perennial. But it does seem to be even more abundant this season, and if you love plaids, checks, or tartans, you’ll have a good selection to choose from.
I’ve had a hankering for one of these Pendleton plaid “49er” jackets ever since Julia Roberts’ character wore one in Mona Lisa Smile (2003).
My sizes: Jacket – Small, Tee – Small, Jeans – 28 Petite
Over the years I’ve searched periodically (new and vintage), but never hit the right colors in my size. While thumbing through a Pendleton catalog recently, this one grabbed my attention and I jumped on it. I’ve styled here with a tee, vintage Murano glass bead necklace, resin bracelet, Madewell darted barrel jeans, and sleek square-toe loafers.
Adding pattern can be a great way to bring a focal point and add interest to simple outfits. But not all prints are created equal…timeless patterns like plaids, checks, stripes, dots, paisley, and some animal prints will have the longest shelf life. A plaid jacket in your best colors is one of those pieces you’ll return to year after year!
If there’s a plaid jacket on your fall wishlist, take a peek at these:
(Click images to shop.)
The Best Loafers for Fall & Travel (A Timeless Wardrobe Staple)
Loafers are not only stylish, but another timeless fall fashion “trend.” And they can be an excellent shoe for travel, offering both practicality and versatility.
I’ve been searching for a pair that balances comfort, support, and style, especially for travel. These from Cole Haan tick all the boxes! They have support and cushioning in the insole, and the lug sole provides traction on wet or slick surfaces. This style is available in four colors/finishes, and runs true-to-size (with enough room for socks). A classic penny loafer or driving moccasin is the kind of shoe that earns its keep, carrying you stylishly through season after season.
More timeless & comfy loafers
Tie One On…How to Wear a Silk Scarf This Fall
Silk scarves have re-joined the chat!
Silk scarves were featured by several influential brands on the fall runways. And I’ve noticed an uptick in styles being offered across various retailers. I’ve been going through my scarf stash and pulling out some of my favorites to wear once the weather cools.
If a standard size silk square feels like too much to wrangle, try one of these smaller bandana-sized scarves:
Trends may come and go, but timeless pieces always find their way back each fall. Styles like these with staying power can help build a wardrobe that works year after year. Whether you’re refreshing with a new piece or shopping your own closet, these perennial fall fashion favorites are always worth revisiting. What are your favorite fall “perennial” styles?
I can’t wait to read what my friends have shared; please do go visit their lovely blogs!
Annie: Most Lovely Things
Mary Ann: Classic Casual Home
Cindy: Cindy Hattersley Design
Noelani: La Vie On Grand
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I love a silk scarf and will always wear one! I am so happy to see lots of styles this season as they are the perfect touch to any outfit. I love how you have show yours styled in your hair, so chic. That’s not a look I’ve tried yet, but you make it look great!
Thanks very much, Noelani! I’m absolutely swooning over the loafers you included in your post, and have a pair in my cart! 😉
That Pendleton jacket is a great find! The colors are spot on for you and I love how you’ve styled it!
Susan—I love your Pendleton jacket! And the silk scarves and how you wear them! I’m a bit challenged when it comes to scarves, but this is inspiring me to try again!
Xo
Annie
Thanks so much, Annie! I think the key with scarves is just to practice with a few different simple ties, and find 2 or 3 you like.
Thanks so much, Caroline!
I own my mother’s 49er jacket from the 1950s. I don’t know what to do with it because it’s too small for me to wear. It’s in yellow and gray.
Hi Leslie, do you have any consignment or vintage shops nearby? I’ll bet they’d be delighted to help you sell it.
Could you comment on whether the 49’er jacket wool is scratchy? I also have looked at these over the years (my Mom had one, probably from the original ‘49 launch!) so I have a sentimental attachment. When there used to be a Pendleton store near me, I found that much of their wool was Shetland, or other versions that were scratchy (I usually look for merino wool). BTW those colors are perfect for you and I think they would work also for me……I am a spring with some autumn. Mom was a redhead and (this was well before color-matching) her fave colors were orange and green.
Hi Sheila, for someone who is sensitive to wool, it might be a bit scratchy, but I wore it over a tee and was comfortable. (Mostly I’d be wearing over long sleeves.)
OMG! I thought I was the only one who fell in love with Julie Robert’s Pendleton jacket in “Mona Lisa Smile”. Good movie, wonderful costumes. As I remember, she also had a lovely, large pin on the jacket.
Thanks for the memory!
I loved the costuming in that movie…it was all so well done!
You look fabulous, Susan, in the plaid jacket and barrel jeans! And we agree on the silk scarves! You have the best taste!!!
Thanks so much, Mary Ann!
Susan that jacket!! Now I am coveting one! I love vintage jackets and the colors in that one are wonderful! I wish Cole Haan made those loafers in a wide. I would jump on them as well!
Thanks, Cindy! I think these jackets are so iconic. I don’t know how wide your foot is, but I find this style quite roomy in the toe box.
Hi! Fall looks for “winters”!?
Coming next week!
I love the loafers! But what kind of no-show socks do you wear that don’t slip down?
I’ve had very good luck with these: https://go.shopmy.us/p-19593198 And when the weather cools, I’ll wear regular cotton or wool socks.
Love the Pendleton jacket on you. The jacket is so authentic and you have the eye and taste to recognize that. I lost my beautiful Pendleton coat in the January fires and I’m looking to find it again on Enay and other sites.
Hi Susan,
You look so terrific in your Pendleton jacket the whole look is wonderful! Thank you for sharing. I loved the film Mona Lisa. I had a green plaid jacket in my early twenties I bought from a famous second hand store in London called ‘American Rag’ in London and I loved everything about it! Happy to hear silk scarves are in I bought the red Elizabetta bandana scarf similar to you to take traveling with me.
Have a lovely day!
Hi Francesca, thanks and enjoy that scarf!
I, too, have been looking for the perfect plaid jacket. I just ordered the 49’er from Pendleton. Thank you so much for sharing it with us. Can’t wait to wear it this fall and winter.
Hi Pam, wonderful, I hope you love it!
I have two 49er jackets that I purchased new over 20 years ago. I love them. My favorite is a pale blue and grey plaid, the other is camel, dark brown and orange plaid. Being from the PNW, my husband and I love Pendleton. He wears their lightweight wool shirts almost year round. Two years ago, he surprised me with the Harding design midi coat in camel. I love it, as does my daughter who is hoping I will tire of it. No way!
They all sound like wonderful pieces!
Love your Pendleton jacket!
Thanks, Kay!
Great post, and thanks for the Pendelton recommendation – I plan to buy one.
Are those classic Paul Green Munchen shoes you’re wearing? If so, I have the same pair and love them.
I never liked loafers, not even as a teenager. But…I do see how comfortable they are. I am more for pointy nose shoes and admit that they usually squeeze my toes.
Although I like you in your plaited jacket, again, it is not something I am drawn to. But never say never as I told you last week I was not going to buy any brown clothes…so far I bought a pair of brown vegan leather (love that expression) trousers and a brown jacket. I often have to eat my words.
Greetje
I think the fact that we all like different things (and that our likes can evolve over time) is what makes style so fascinating. And I can’t wait to see your brown pieces.
Great post!
I love your take on scarfs. It gets a bit warm here in Florida. But I do plan to incorporate them into my fall and winter wardrobe.
Thanks, Rosemary!
Nice Pendleton jacket.
Thank you!
Susan, absolutely love your new fireplace lamps and shades. Such a happy, whimsical look!
Thanks, Lee!