10 More “Timeless” Pieces That Are Actually Dating Your Style

Okay, it’s back — another round of so-called “timeless” pieces that are anything but. I’m talking about those items that quietly sabotage your outfit and make your entire look feel stuck in a past decade.

Before we dive into the list, I want to share the philosophy that shapes everything I teach. It’s the standard I use to evaluate every outfit. Picture a triangle with three corners:

1. You love it.
2. It loves you back (fit, color, flattery).
3. It’s modern (i.e., still relevant in today’s style landscape).

All three corners matter. If you’re only dressing based on what you love, but the piece doesn’t flatter you or it looks dated, you’re not going to feel your best. That’s why “just wear what makes you happy” isn’t actually helpful advice. We deserve more than that. We deserve to feel beautiful and current.

So with that said, let’s talk about 10 more pieces that might be quietly working against your style — and what to do instead.

Find all of the modern versions of these pieces in this catalog.

1. The Infinity Scarf

Especially chunky ones. It was the “cool mom uniform” in 2010: infinity scarf, long tee, skinny jeans, taupe booties. That era is over. Scarves are in — but they’re silk, square, and styled with intention. If you still love your infinity scarf, archive it for now. It’s not the vibe in 2025.

Instead, try a silk scarf for fall. They are a huge trend styled in fresh new ways.

2. The Jersey Empire Waist Maxi Dress

You know the one. Ultra-thin fabric, gathered high at the bust, clings to everything. These dresses are everywhere because we keep buying them. But that doesn’t mean they’re still stylish. Want a jersey dress that’s modern? Try Diane von Furstenberg or Boden — they get it right.

If you love jersey dresses, like I do, try modern versions from Quince, Boden, and Diane von Furstenberg. Find these modern versions in this catalog.

3. The Waterfall Cardigan

Drapey? More like droopy. These cardigans are supposed to be flattering, but they end up looking shapeless and dated. Instead, go for a structured cardigan or knit jacket with a clean hem and some shape.

Instead, try a structured cardigan or light jacket, which will work much better with today’s current outfits. Find these modern versions in this catalog.

4. The Peter Pan Collar Button-Down

Can we stop infantilizing women over 50 with toddler-level details? Between the puff sleeves, cutesy prints, and the actual Peter Pan collar, this blouse is a one-way ticket to Frumpsville. A classic short-sleeve blouse? Yes. But skip the baby collars.

Try a shirt that is cute, not cutesy, like one of these elevated versions. Find these modern versions in this catalog.

5. The Fabric Purse (You Know the One)

Looking at you, Vera Bradley. These quilted, paisley-print bags may be beloved, but they’ve never really been in style. If you love the shape, try it in a solid neutral — it’ll be way more versatile.

Solid neutral versions of these bags are so much better. Find these modern versions in this catalog.

6. The Too-Tight Button-Down Shirt

If it gaps at the bust and hugs your midsection like Spanx, it’s not your friend. These shrunken-fit blouses were everywhere a decade ago, but today’s button-downs are relaxed, tailored, or even oversized — and so much more flattering.

Try a menswear inspired button down in a medium tailored fit or a slightly oversized fit for a more modern look. Find these modern versions in this catalog.

7. The “Wrong Length” Trench

There’s cropped and there’s full-length. That in-between knee-length trench that hugs your waist? Not it. If you want a timeless investment trench, look for something with a classic silhouette — think Burberry Kensington vibes.

Try a trendy cropped trench or a truly timeless full length trench instead. Find these modern versions in this catalog.

8. Colored Skinny Jeans

I had the mint green pair. You probably did too. Skinny jeans in pastel or maroon had their moment, but it’s over. If you want color, go for tailored trousers or jewel-toned wide-leg pants. Not skinnies.

Try a pair of straight leg velvet jeans in a jewel tone, or a pair of colored trousers. Find these modern versions in this catalog.

9. Cork or Patent Wedges (Especially Peep Toe)

I’m not anti-wedges — they’re starting to return in sleek, sculptural forms. But cork soles with patent leather uppers and a peep toe? That’s a very specific 2012 look, and it hasn’t been back since.

Try an espadrille or one of the new modern wedges. Find these modern versions in this catalog.

10. The Basic Fleece Zip-Up

Yes, they’re cozy. But unless you’re hiking or running errands, they have no business in your outfit rotation. Reach for a waist-length cardigan, knit blazer, or lightweight jacket instead. You deserve stylish comfort.

Try a more versatile jacket that elevates your outfits. Find these modern versions in this catalog.

Bonus: Dated Embellished Pieces

A little sparkle is fabulous — but a sequin-trimmed cardigan from 2013 isn’t. Statement details age fast. If it’s been more than 5–7 years and it looks “fancy” in a way that’s oddly familiar, it’s probably dated. Exceptions? A neutral sequin shell or jacket with a clean silhouette can still work.

Try a solid all over sequin pieces or embellished styles from contemporary brands. Find these modern versions in this catalog.

I know some of this might feel harsh. And if one of these pieces is your absolute favorite — archive it. Style is cyclical, and it might come back. But if you want to look modern and relevant now, these are the pieces that are holding you back.

Trends aren’t subjective — they’re based on patterns, shifts, and cultural context. And I’ve spent over 30 years in this industry tracking them, researching them, and helping women navigate them with style and confidence.

If this resonates with you, I invite you to join me for my ongoing Style Masterclass Series — we meet about every other week and talk outfits, trends, and what actually works for your life now. Details are in the YouTube description and pinned comment.

And if you haven’t yet grabbed my Modern Classics Wardrobe Guide, now’s the time. It’s full of the pieces that are truly timeless in 2025 — and worth investing in.

Let’s keep building wardrobes that love us back.