8 designer purchases Boomer women save for that lose value the moment they leave the store

When my mother introduced me as "my daughter who worked in finance" for probably the hundredth time instead of "my daughter the writer," I noticed something in her closet. A pristine Coach bag from the late 1990s, still wrapped in tissue paper. She'd saved for months to buy it, convinced it was an investment piece.

That bag is now worth about 40 percent of what she paid.

During my almost 20 years as a financial analyst, I learned to read between the numbers and understand what things were really worth. The same analytical skills that helped me evaluate market trends now help me see through the marketing hype around "investment" designer pieces.

Here's what I've learned about luxury purchases that depreciate faster than most Boomer women realize.

1) Designer shoes worn even once

You know how a new car loses value the moment you drive it off the lot? Designer shoes are worse.

I used to think my expensive work heels were sensible investments because of their quality. Then I tried to resell a pair of barely worn designer pumps and got a reality check. Shoes worn just once can lose anywhere from 20 to 50 percent of their value immediately.

The reasons are pretty straightforward when you think about it. People are understandably squeamish about buying shoes someone else has worn. And unlike bags or jewelry, shoes show wear faster because they're literally taking the brunt of your body weight with every step.

Even high-end designer shoes from brands like Louboutin depreciate significantly after wear. The moment those red soles touch the pavement, the resale value plummets. Sure, they're beautiful, but they're not holding their value the way the sales associate suggested when you bought them.

2) Trendy designer clothing pieces

That statement blazer or logo-heavy dress might feel like an achievement when you first buy it. I remember my first designer work suit, bought during my junior analyst days when I was trying to look the part.

The problem with trendy designer clothing is that fashion moves faster than the depreciation schedules I used to analyze. A piece that's hot for one or two seasons becomes dated quickly, and suddenly you're stuck with something expensive that you can't wear without looking out of touch.

Classic designer pieces might fare better, but anything tied to a specific trend or season will lose most of its value within a year or two. You're essentially renting the piece for an exorbitant upfront cost.

Unlike handbags or jewelry that can transcend trends, clothing is deeply personal and suffers from both style changes and visible wear. Most designer apparel loses significant resale value unless it's a genuine archival or vintage piece that comes back into fashion decades later.

3) Logo-heavy accessories with limited appeal

During the 2008 financial crisis, I watched clients panic-sell luxury goods to cover losses. The pieces that sat longest on resale platforms? Logo-covered accessories that screamed brand name but offered little else.

When an accessory's entire value proposition is showing off a logo, you're betting that logo will stay relevant. Fashion houses change creative directors, trends shift, and suddenly your logo-print wallet or belt is a reminder of a specific era rather than a timeless piece.

These items also face another challenge in the resale market. Because they're so recognizable and often counterfeited, buyers become skeptical. Proving authenticity becomes a hassle, and even when you can, the market is flooded with similar pieces.

The accessories that hold value tend to be those with subtle branding and classic design elements. Think simple leather goods with minimal logos rather than monogram canvas pieces.

4) Entry-level luxury handbags from declining brands

Not all designer bags are created equal when it comes to resale value.

I learned this the hard way with a Coach bag I bought in my late twenties. Back then, Coach felt like an achievement. The leather was substantial, the hardware was solid. But the brand expanded too quickly, opened too many outlet stores, and the prestige evaporated.

Entry-level bags from brands that have diluted their luxury status through mass production and constant sales rarely hold their value. When you can regularly find 40 to 50 percent discounts at outlet malls, why would anyone pay close to full price on the resale market?

Brands like Coach, Michael Kors, and Kate Spade once commanded respect and premium prices. Now their entry-level pieces depreciate rapidly because the market is oversaturated and the exclusivity is gone.

If you're buying a bag as an investment, it needs to be from a brand that maintains scarcity and quality. Think Hermès, Chanel, or certain Louis Vuitton classics. Anything else is really just a purchase for personal enjoyment, not a financial asset.

5) Designer sunglasses with last season's style

Sunglasses are particularly brutal in the depreciation game because they combine several value-destroying factors. They're fragile, they go out of style quickly, and they're deeply personal in terms of fit and face shape.

That pair of designer sunglasses you saved up for? They're probably worth less than half what you paid within a year, even if you've barely worn them.

The eyewear market is also flooded with discounted authentic pieces and high-quality replicas, making it tough to get good resale prices. Plus, prescription sunglasses are nearly impossible to resell at any meaningful value because they're customized to your specific vision needs.

I used to justify expensive sunglasses by calculating cost per wear. But that's not the same as resale value. You're essentially prepaying for temporary use of a fashion accessory, not acquiring an asset.

6) Luxury watches from fashion brands rather than watchmakers

There's a huge difference between a watch from a fashion house and a watch from an actual watchmaking company.

Fashion brand watches like those from Gucci, Louis Vuitton, or Dior depreciate significantly because serious watch collectors don't view them as true timepieces. They're fashion accessories with watch movements, not horological investments.

Meanwhile, watches from dedicated watchmakers like Rolex, Patek Philippe, or Omega can actually appreciate or at least hold steady value. The difference comes down to craftsmanship, limited production, and a collector market that values the mechanical aspects of the watch itself.

If you're buying a luxury watch thinking it will hold value, stick with actual watch manufacturers. Otherwise, you're paying a premium for a brand name on something that will function no better than a significantly cheaper timepiece while losing value just as quickly.

7) Seasonal designer jewelry pieces

During my time volunteering at farmers' markets, I've met women who regret spending thousands on trendy jewelry pieces that now sit unworn in their drawers.

Costume jewelry from luxury fashion houses might carry a prestigious label, but it depreciates rapidly because it lacks the intrinsic material value of fine jewelry. You're paying for design and branding, both of which fade with fashion cycles.

Even when the materials are decent, seasonal designs become dated quickly. That chunky statement necklace or logo-heavy bracelet from a few years ago? It screams its era in a way that makes it difficult to wear or resell.

Fine jewelry from dedicated jewelry houses tends to hold value better because the materials themselves have worth and the designs are more timeless. A simple gold bracelet or classic diamond piece will always have its metal and stone value as a floor, regardless of fashion trends.

8) Limited edition collaborations with quick saturation

This one surprised me when I first started paying attention to the resale market.

Limited edition collaborations between designers and brands sound like they should be valuable. Limited means scarce, right? But many of these "limited" releases get produced in large enough quantities that the market gets saturated quickly.

I've seen Boomer women spend premium prices on designer collaborations with the belief they're getting something rare and investment-worthy. Then within months, the resale market is flooded with similar pieces, and values tank.

The collaborations that do hold value tend to be extremely limited runs with genuine scarcity. Most mainstream designer collaborations produce enough units to capture the hype without maintaining true rarity.

Unless you're absolutely certain about the production numbers and have a genuine passion for the piece itself, these collaborations are purchases for enjoyment, not investments.

Conclusion

After spending years analyzing investments and their returns, I can tell you that most designer purchases shouldn't be viewed as financial investments at all. They're consumption choices, and that's perfectly fine as long as you're honest about what you're buying.

The Boomer generation often learned to view certain luxury purchases as assets because they were marketed that way. Quality was supposed to mean value retention. Designer labels were supposed to signify lasting worth.

But the luxury market has changed dramatically. Production has ramped up, brand prestige has been diluted, and the resale market has become sophisticated enough to price things at their true secondary market value rather than their aspirational one.

Buy designer pieces because you love them and will use them, not because you think they'll hold value. The joy of wearing something beautiful for years is its own return on investment, even if the financial return is disappointing.

And if you do want purchases that appreciate? Put that money into actual investments instead. After all my years in finance, I can promise you a diversified portfolio will treat you better than a closet full of depreciating designer goods.