How to Rock “Eclectic Grandpa” Style After 40 (Yes, Really!)

Ladies – remember when we were teenagers, raiding our dad’s and grandpa’s closets for those grungy vintage T-shirts and oversized jackets? The 90’s vibes were EVERYTHING.

Well, gather round, because it’s time for another trip down memory lane! This year the trend for “Eclectic Grandpa” is going to be HUGE!

The Eclectic Grandpa fashion trend is bringing back that quirky, edgy grandpa chic style with a modern twist. And guess what? We can totally rock this look over 40!

What does “Eclectic Grandpa” mean?

I know, I know – when I first heard “grandpa fashion,” I pictured those baggy plaid pants pulled up to the chest with suspenders. A look that only sophisticated gentlemen like my grandpa could pull off.

But today’s grandpa chic is nothing like that! It’s an artful mix of vintage, outdoorsy and tailored pieces for an intellectual yet relaxed vibe.

Think oversized cozy cardigans, retro glasses, pleated trousers, sweater vests. It’s like rugged professor meets lumberjack meets collage art major. What’s not to love?

As always when trying a new style, fit is key. The slouchy silhouettes are super flattering for our 40-something bodies. No squeezing into tight clothes – phew!

And the earthy color palette means this trend works all year round. Mustard, olive green, rusty orange – these soulful hues are perfect for fall and beyond.

Here’s how to dip your toes into the eclectic grandpa aesthetic while feeling comfortable and confident!

Simple outfit formula of “Eclectic Grandpa”

Start with relaxed slacks, jeans or Bermuda shorts.

Layer on an oversized button-down, vintage tee or sweater.

Finish with a cardigan, blazer or vest for texture.

Tie it all together with retro sneakers, loafers or sandals.

Keep accessories minimal – delicate necklaces, round glasses, beanies or newsboy caps.

With this adaptable formula, you can create so many chic grandpa-style looks!

For business casual, try high-waisted pleated trousers with a linen button-down, knit vest and loafers.

Going casual? Style straight-leg jeans with a graphic band tee, cozy flannel and sneakers.

For colder days, Bermuda shorts with tights, an Aran sweater and beanie is the perfect weekend outfit.

Let’s look at some specific ways to nail the vibe.

Must-have pieces from “Eclectic Grandpa” that especially suit women over 40

1. Pleated Pants

A classic grandpa staple, pleated pants instantly evoke the quirky style of the ’90s. They come in fun prints or earth tones like sage, stone and nutmeg. For a more polished look, try a high-waisted version with a belt and button-down. Or style loose pleated pants with a Blondie tee and cardigan for an edgy daytime vibe.

The billowing silhouette moves with you and is so comfortable! Say goodbye to stiff, clingy clothes.

2. Worker or Leather Jackets

A rugged worker jacket or classic moto-style leather jacket captures the rebellious spirit of a vintage grandpa’s wardrobe. With cool details like shoulder yoke panels, zippers and snaps, they’re the ultimate retro-inspired topper.

For style, I love pairing a worn-in work jacket or buttery leather jacket with a floral midi dress and lace-up boots. Roll up the sleeves for a laid-back vibe.

Or contrast the edgy jacket with elegant pants and loafers for an eclectic look.

The oversized silhouette flatters all figures by cinching in at the waist. And leather or denim only gets better with age – break yours in for that coveted weathered look.

Whether you choose structured denim or supple leather, these jackets give a nod to grandpa’s old-school wardrobe while still feeling modern and chic.

3. Cozy Knits

Nothing feels more cozy and “grandfatherly” than an oversized cable-knit sweater or Aran cardigan. The slouchy shapes show off your collarbones and feel amazing layered over tees and button-downs.

Keep the look sophisticated by choosing knits in navy, gray, camel or off-white. Or add a touch of whimsy with an earthy Nordic pattern. Finish with tailored pants and loafers for work, or jeans and sneakers for a weekend get-together. Hygge heaven!

4. Blazers

For an upscale take on grandpa chic, opt for a tailored, menswear-inspired blazer. Strong shoulders and a boxy shape provide structure, while fabrics like tweed or houndstooth add professorial flair.

I like to contrast the casual texture of a tweed blazer with sleek pants or a silky cami. And vintage script buttons make any blazer feel unique.

This lightweight layer is a nod to grandpa’s classic style. But the soft draping and luxe fabrics keep it fresh. It’s the perfect transitional piece for the office, events or a night out.

5. Oldish Frame Glasses

Clear lenses with round or oval frames add a sophisticated flair. Look for retro-inspired styles in tortoiseshell, black and brown-they look so chic with oversized knits and button-downs!

Or grab actual vintage shades from the thrift store. I found a cool pair from the ’70s for only 3 Euro in a Parisian brocant!

Old frames bring out your inner librarian. But the thin metal or acetate styles keep a modern edge.

Simple outfit idea in the “Eclectic Grandpa” style

Okay, so these are some of my favorite pieces to create Eclectic Grandpa outfits. As you can see, the look is all about mixing old-school vibes with new-school pieces.

And here is a simple outfit idea in the “Eclectic Grandpa” style that you can try (and not for all the money in the world).

Start with everything really simple (everything from Zara): worker jacket, pants, long sleeve, polo, add shoes, and of course this retro sunglasses, and finish the look with this gorgeous bag from Miu Miu (because we at our 40s can afford such a bag!)))

There are so many ways to get creative and make this trend your own! Don’t be afraid to raid your partner’s closet for vintage band tees, comfy flannels and linen shirts.

My best tip is to start small – add just one “grandpa” piece to your usual outfit, like high-waisted pleated pants or an oversized cable knit. As you get more comfortable, build up your edgy grandpa ensemble.

The most important thing is that you feel totally confident and amazing in whatever you wear! Don’t change your style too drastically. Pick pieces that make you smile, like cozy silhouettes, fun prints, or special textures.

I don’t know about you, but I’m loving the revival of my ’90s thrifting days with this trend! More vintage tees and cozy knits, please.

Let me know if you try the Eclectic Grandpa look. We can trade outfit pics and style tips in the comments below. Have fun and stay true to YOU!


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