7 subtle fashion choices that immediately signal you're trying too hard to look wealthy

Ever notice how some people's outfits scream "expensive" but somehow feel... off? Like they're wearing a costume rather than clothes?

There's a fascinating psychology behind this. When we try too hard to signal wealth through fashion, we often end up broadcasting insecurity instead. The truly wealthy rarely need to prove anything through their wardrobe.

Living in Venice Beach, I see this play out daily. From the boardwalk to Abbot Kinney, there's this constant parade of people trying to project success through their clothing choices.

And after years of observing (and yes, photographing) street style here, I've noticed some patterns.

Let's explore the subtle fashion choices that immediately give away when someone's trying too hard.

1. Logos everywhere, all at once

You know what I'm talking about. The Louis Vuitton bag, Gucci belt, Balenciaga sneakers, and Versace sunglasses all in one outfit.

Real wealth whispers. It doesn't need to shout through every available surface.

I once met a tech founder at a coffee shop in Marina del Rey. Worth millions. Wearing a plain white t-shirt, well-fitted jeans, and sneakers I couldn't identify. Meanwhile, the person next to him had designer logos from head to toe and kept checking if people noticed.

Which one do you think felt more secure in their success?

When every item you wear screams a brand name, you're essentially turning yourself into a walking advertisement. And advertisements, by nature, are trying to sell something. In this case, an image that probably doesn't need selling if it were authentic.

2. Brand new everything, pristine condition

Have you ever noticed how the wealthiest people often wear clothes that look lived-in? There's a reason for this.

When everything you own looks like it just came off the rack yesterday, with tags practically still attached, it suggests you just bought it all at once. Maybe to impress. Maybe to fit in somewhere new.

True luxury items get better with age. A quality leather bag develops character. Good denim molds to your body. Expensive watches gain scratches that tell stories.

The desperate need to keep everything pristine, wrapped in plastic, babied to death? That's fear of losing something you can't easily replace.

3. Overdressing for every occasion

Showing up to brunch in a three-piece suit. Wearing stilettos to a backyard barbecue. Sporting a Rolex to the gym.

Context matters more than cost.

I've mentioned this before, but understanding social cues and dressing appropriately shows genuine sophistication. The wealthy don't need to flex at every opportunity because they're comfortable in their skin regardless of what they're wearing.

Last week, I photographed a charity event in Malibu. The hosts, who'd donated millions, wore simple linen shirts and sandals. Some guests showed up looking ready for the Met Gala. Guess who looked more comfortable and confident?

When you overdress consistently, you're announcing that you don't understand the social dynamics of the spaces you're in. Or worse, that you need your clothes to speak for you because you're not confident your presence alone is enough.

4. Fake luxury items trying to pass as real

This one's tricky because I'm not talking about people who knowingly buy replicas and own it. I'm talking about those who buy fakes and insist they're real.

Why does this signal trying too hard? Because it shows you value the perception of wealth over authenticity.

Here's what's interesting from a psychological perspective: people who can actually afford luxury items often don't care if others think their stuff is real or fake. They know what they have. They don't need validation.

But when someone gets defensive about their "authentic" Hermès bag that has slightly off stitching? That desperation to be believed reveals everything.

5. Uncomfortable in your own clothes

Ever watch someone constantly adjusting their expensive watch? Wobbling in designer shoes they can't walk in? Refusing to sit normally because their outfit might wrinkle?

Comfort and confidence go hand in hand.

The wealthy buy clothes that fit their lifestyle, not the other way around. They choose pieces they can move in, live in, work in.

I learned this lesson myself after buying an expensive jacket that required dry cleaning after every wear. Found myself never wearing it because I was always worried about messing it up. My partner finally asked why I bought something that made me so anxious. Good question.

Now I stick to pieces that work with my life, not against it. And ironically, I probably look better because I'm not constantly fidgeting or worried.

6. Talking about how much things cost

This might be the most obvious tell of all.

"These shoes? Oh, they're Louboutins. $1,200. Got them on sale though, only $900."

Nobody asked. Nobody needed to know.

People with genuine wealth rarely discuss prices. Why? Because money isn't novel to them. It's like asking someone to get excited about having running water. Sure, it's nice, but it's not conversation-worthy.

When you volunteer price tags, you're essentially saying, "Please be impressed by my ability to spend money." But spending money isn't an achievement. Anyone with a credit card can do it.

7. Zero personal style underneath the labels

Here's a question: If you removed all the labels from your wardrobe, would your outfits still have personality?

This is perhaps the subtlest sign of trying too hard. When someone dresses exclusively in whatever's trending in luxury fashion, without any personal touch or individual style, they're essentially admitting they need brands to create an identity for them.

True style transcends labels. It's about understanding what works for your body, your lifestyle, your personality. It's mixing high and low, vintage and new, designer and thrift.

Some of the best-dressed people I know shop everywhere. They'll pair a vintage t-shirt with designer jeans, or throw a thrift store jacket over a expensive dress. They're not trying to look rich. They're trying to look like themselves.

Wrapping up

Fashion should be fun. It should be personal. It should make you feel good.

When it becomes a desperate performance of wealth, it stops being any of those things. Instead, it becomes a burden, a source of anxiety, a constant worry about whether you're projecting the "right" image.

The irony? The people you're trying to impress can usually tell. And the ones who can't probably aren't worth impressing anyway.

Real confidence doesn't need designer validation. Real wealth doesn't need to announce itself. And real style? That comes from knowing who you are, not from what you can afford to buy.

Next time you get dressed, ask yourself: Am I wearing this because I love it? Or because I want others to think something specific about me?

The answer might surprise you.