If a boomer still wears these 7 things regularly, they probably don’t realize how outdated they look

We all have favorite pieces we’ve loved for years, don’t we?

A jacket that’s seen you through promotions. A pair of shoes that knows every sidewalk on your block. There’s real comfort in clothing that feels like an old friend.

But sometimes, those beloved staples quietly date us more than we realize.

I’m not talking about age — I’m talking about era.

When clients come into my office feeling “invisible” or “overlooked,” we often discover the issue isn’t confidence. It’s that their wardrobe is sending a timestamp they never intended.

Clothes are nonverbal cues, what psychologists call enclothed cognition. What we wear influences how we feel and how others read us. The goal is to keep your signals current while staying completely yourself.

With that spirit—zero shaming, all care—here are 7 pieces I often see worn on repeat that can make someone look more dated than they are, plus what to try instead.

1. That boxy blazer with throwback shoulder pads

I know the one. Long line, stiff fabric, strong shoulders, and a fit that floats around your frame rather than meeting it.

The problem isn’t blazers — they’re timeless. It’s the structure.

Big pads and a long, straight body create a 1980s outline that reads boardroom-power, not modern polish. The eye reads proportion first, and those proportions tell a different decade’s story.

What to try instead: an unstructured or softly tailored blazer with a bit of drape and a defined shoulder (not padded), ending around mid-hip or just below.

Look for darts or subtle shaping through the waist, or a single-button style that creates an easy V. For men, aim for a jacket where the seam rests right at the edge of your shoulder and the sleeves show a sliver of shirt cuff.

As Steve Jobs said, “Simple can be harder than complex.”

The modern blazer embraces that simplicity — clean lines, breathable fabric, and ease of movement. You’ll look current and feel less armored.

2. Square-toe dress shoes (and marshmallow sneakers)

Footwear dates faster than almost anything else.

Square-toe loafers and dress shoes had a huge run — so did pillowy, ultra-cushioned “dad” sneakers.

Both skew practical, but together they broadcast “comfort first, style second” in a way that can undermine an otherwise sharp outfit.

What to try instead: an almond- or round-toe shoe in a matte leather or suede. For loafers, look for a slimmer profile. For sneakers, think minimal—clean leather or canvas, low profile, uncomplicated sole. Keep the white bright or go tonal with your pants for a longer line.

Warren Buffett’s reminder works here: “Price is what you pay; value is what you get.” A well-made, simple shoe will quietly elevate everything you wear for years, not months.

3. Pleated khakis with puddling hems

Pleats and break (the way pants meet your shoes) are tiny details with outsized impact.

Heavy front pleats and wide legs that puddle over shoes were standard for a long time.

Today, the silhouette has shifted toward cleaner fronts and hems that kiss the top of your footwear. Extra fabric collects visual weight at the ankle and reads dated fast.

What to try instead: flat-front chinos or trousers in a straight or gentle taper. Aim for a “slight break” at the hem—no pooling. If you love a pleat for comfort, choose a single, subtle pleat and pair it with a trim leg. Tailoring is your friend here. A simple hem or slight taper can transform pants you already own.

Clients often tell me they feel “taller” and “lighter” after this change.

That’s processing fluency at work — the brain prefers clean lines it can read quickly, which we tend to interpret as modern and put-together.

4. Capris and long tunic tops that hide your shape

I see this combo constantly because it feels safe.

Mid-calf pants plus a long, flowy top promise coverage and comfort.

The catch?

Cropped pants that hit halfway down the calf visually shorten the leg, and tunics that cover the fullest part of your hips erase your natural shape. The overall effect is boxy, especially from a distance, and it can add years you didn’t sign up for.

What to try instead: ankle pants (not mid-calf) with a straight leg, ending just above the ankle bone. Pair them with tops that hit at high hip or the top of the thigh — enough length for ease, but short enough to show your proportions.

If you like flow, choose a soft A-line that skims rather than swallows.

A quick fit test I give clients: stand side-on in a mirror.

Do you see the curve of your waist or the line of your hips at all?

If the answer is “not really,” try a shorter top or a front tuck. A little structure goes a long way.

5. Matching jewelry sets and heavy statement necklaces

Remember the boxed sets — earrings, necklace, bracelet — all in the same stones and metal? Or the chunky, multi-strand statement necklaces that were everywhere in the 2000s?

Matching sets and oversized necklaces pull the eye in a way that can fight against today’s cleaner necklines and simpler hardware. They also telegraph “I bought the set,” which reads more formal than most of us dress day-to-day.

What to try instead: one focal point at a time. Delicate mixed metals, a single pendant, small hoops, or a cuff. If you love color, choose one strong piece and let it breathe.

Scarves can replace a heavy necklace for interest near the face — try lightweight, solid or micro-print styles in modern ties (a loose knot or drape rather than tight, fussy folds).

Dale Carnegie said, “A person’s name is to that person the sweetest and most important sound.”

The modern jewelry equivalent?

Pieces that frame your face, not steal the show from it.

6. Tiny wireframe glasses with gradient tints (plus the neck chain that never leaves)

Vision is personal terrain, and comfort matters. Still, small, narrow wireframes and brown-to-clear gradient tints can stamp a look to a particular decade.

Add a permanent neck cord, and we’re deep in “function over form”—useful, yes, but unintentionally aging.

What to try instead: slightly larger lenses that follow your brow line and show more eye.

Tortoiseshell, soft black, or translucent acetate modernizes quickly.

If you need readers, consider a slim case that slips into your bag and a stylish chain you wear sometimes, not always. Blue-light or clear lenses with subtle anti-glare also read cleaner in photos and under restaurant lighting.

A tiny shift in frames can make the whole face look fresher because eyes are where people connect first.

7. The golf-course uniform: tucked logo polo, braided belt, cargo shorts

You know this outfit: branded polo tucked in tight, braided leather belt, phone holster, cargo shorts with flaps, white crew socks pulled mid-calf, chunky sneakers.

It’s practical. It’s familiar. It also says “off-duty 2007.”

What to try instead: polos with a softer collar in a breathable pique or jersey, worn untucked if the length hits mid-zipper to mid-pocket (the modern sweet spot).

Swap the braided belt for a clean leather style, and trade cargo shorts for flat-front shorts with a 7–9 inch inseam (adjust for height).

Socks either ankle-length or clean crew, not bunched halfway. If you carry your phone on your belt, try a slim crossbody or a pocket with a case that slides smoothly.

For women, the parallel is the logo tee tucked tight into long denim capris with a heavy belt and athletic sandals. Same update: cleaner tee or knit polo, ankle-length jeans with a straight leg, streamlined belt, and leather sandals or simple sneakers.

“Seek first to understand, then to be understood,” Stephen Covey wrote.

When I translate that to closets, it sounds like this: understand the function you want (ease, pockets, sun protection), then choose the form that does it now.

Final thoughts

At the end of the day, style isn’t about pretending to be a different generation. It’s about letting the outside match the inside—competent, current, and fully you.

These seven items aren’t “bad.” They’re just carrying timestamps you may not intend to broadcast.

If you’re ready to experiment, try this two-week reset:

Choose one category to upgrade (shoes or glasses offer the fastest return).
Tailor a pair of pants to your ideal hem.
Build a simple “go-to” outfit formula—your version of a uniform.
Donate two dated pieces you won’t miss.
Ask a trusted friend to snap candids of you in your refreshed look. We perceive ourselves differently in motion than in a mirror; photos help you see what others see.

You don’t have to keep up with trends to look modern. You only have to keep up with yourself. The rest takes care of itself.