Fall Fashion for 60+ Women – Would you Wear it Again?

Fall 2025 is basically raiding our old closets for a walk down a trendy Memory Lane.

Designers have dusted off the plaid skirts, slouchy knits, and penny loafers we rocked in our twenties and (thank goodness) given them a fresh, modern twist. Think better fabrics, smarter cuts, and a dash of nostalgia you can actually wear.

This season’s trends feel like a reunion with your younger self and a chance to ask the ultimate question: now that they’re back, would you wear them again?

Plaid is Back

As a private school alum, I have taken a blood oath to never again wear plaid.  

This may be the year I give in.

Updated plaid is everywhere, from Ralph Lauren’s cool tartans to Burberry’s iconic checks. Try a classic plaid blazer over a crisp chambray shirt to channel the academia vibe without feeling like a uniform. Pair a plaid flannel with dark wash jeans and boots for an off duty, “town and country” look.

Would you wear plaid again, or is it too much of a schoolgirl-look for you?

Barn Jackets Beyond the Stables

I can’t wait to pull my brown suede barn jacket out of storage. It’s a 20-year-old favorite that I’ve been known to wear over almost everything—including my pjs for an early morning dog walk.

Today the classic barn jacket—once purely utilitarian—is a fashion essential. The slightly boxy cut and cozy lining make it perfect for weekend errands or a fashionable stroll among falling leaves. It may not be your first pick to pair with athleisure, but it’s a natural with jeans, khakis or a sweater dress. Roll up the sleeves to show off a contrasting lining underneath for an effortless, layered effect.

Would you wear a barn jacket again, or leave it in the tack room?

Modern Prep: Vests, Tweeds & Rugby Stripes

The trick here is to limit yourself to a touch of prep blended with modern silhouettes. A chunky cardigan over slim knits keeps the look fresh while an argyle vest in updated colors like wine and chocolate can be paired with wide leg jeans for a look that is updated, not outdated.

And don’t forget about the classic rugby stripe shirt. It’s the ultimate in prep school chic.

Would you wear modern prep again, or are your rugby days over?

Rich Colors: Purple, Wine & Chocolate Brown

In the ‘80s we loved our jewel tones, so it’s fun to see that after years of stealth-wealth neutrals, this season’s color trends include deep purple, wine and merlot shades that truly feel like fall, especially when paired with chocolate brown—the other big color of the moment.

Imagine a merlot funnel-neck jacket over chocolate brown trousers, finished with a brown suede purse. Even a simple scarf or handbag in these shades instantly upgrades an outfit.

Would you wear these rich colors again, or stick with neutrals?

Cool Classics: Timeless shapes with a Twist of Luxe 

Think tailored blazers over vests, slouchy sweaters with wide-leg trousers, tall boots with A-line skirts and heirloom-inspired jewelry. These pieces honor classic silhouettes while embracing modern luxury, making them endlessly wearable.

Perfect for women who appreciate sophistication with a contemporary edge, they’re the ultimate blend of tradition and trend for the season.

Would you pair favorite classics with soft silhouettes?

Jeans of All Shapes

No fall wardrobe is complete without great denim. This season blends old silhouettes like the classic cuffed jeans we wore in high school with new and updated versions: wide-leg, cropped, cuffed, light or dark wash—even barrel jeans.

For women over 60 searching for the best jeans the answer is variety—keep a few silhouettes on rotation to refresh your outfits.

Would you wear these new shapes or stick with your tried-and-true cut?

Fall Fashion: The Bottom Line

Fall 2025 fashion trends are all about blending old and new—private-school polish with modern ease, classic fabrics with rich colors, and bold textures with everyday wearability.

By asking yourself “Would I wear it again?” you can filter the trends through your own style.

Pick the ones you love, mix them with what’s already in your closet, and step into the season looking chic, confident and completely yourself.

FYI-I do not endorse the above-listed businesses, products and organizations, nor do I receive compensation from them.

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LET’S TALK ABOUT IT:

What's been lurking in the back of your closet and is perfect to wear again this season?

What needs to be left on mothballs--permanently?