"Investment dressing" is a sham

Giving up risk? You'll give up rewards.

Back when I lived in Boston, I had a friend who got a new Fendi bag. And I was very excited about it for her. But she didn’t seem excited. “I really wanted the pink one,” she said, looking over at her gray bag. I was completely mystified! “If you were spending that much money on something, why didn’t you get the color you wanted?” Her answer: “I thought the gray was a better investment.” (And I can relate — see my Hermes story.)

I really hate the phrase “investment dressing.”

Clothes are virtually never an investment. Like cars, they depreciate the second they leave wherever you bought them. Unless you’re buying Chanel and Hermes bags in bulk to sell in a few years, shopping isn’t an investment strategy.

It’s probably obvious, but what this term does well is help us justify purchases. I know this because it was a phrase my team of writers often playfully used to use when I worked at Rue La La to help you rationalize pulling the trigger on that - whatever. And it worked!

But the effect is that we spend money while deluding ourselves into thinking that somehow, with smart thinking, it won’t be a total loss. When the vast majority of the time, it will. And we have to confront that. But what’s worse is what I suspect is happening as a result. That an ocean of “investment dressing” — even more so than social media — is contributing to the same-ification of the way we all look.

What makes something an investment piece? Time and time again, I read, “this will still look good in 20 years.” “The only one I’ll need.” “Will go with everything I own.” To tick those boxes, that item has to be pretty damn straightforward. A black cashmere crewneck sweater. A classic khaki trench. A pair of aviators.

The “personal style is dead” complaint we’ve all been talking about? I don’t think it’s about the rise of social/copying each other/algorithms so much as (1) social media making it so easy to be judgmental, which chills our willingness to experiment (I’ve talked about and will keep talking about this!) and (2) The rise of the “investment dressing illusion.”

If you care about personal style, getting dressed every day is about expressing that style, bringing that you spirit to play outside in the world. Getting dressed isn’t running a hedge fund, but so many of us are hedging. Treating risk as if we’re handling someone’s money rather than dressing ourselves.

Instead of catering to our innermost wishes, we’re looking at what will please the largest number of people (like my friend) for the longest amount of time (like anyone who expresses a wish to look “timeless” - except of course those who generally associate themselves with that style). Both of these inevitably lead to us all looking the same.

When followed to its natural conclusion, it’s an approach will leave us with a closet full of very classic pieces in neutral colors. Again, if that happens to be your personal style, ok! But it’s hard for me to imagine that’s broadly the case. Friends of mine, who are much more classic than I, meld their classic pieces with some experimentation that will inevitably keep them from being the best “investment” or looking the most acceptable over time.

Like my friend Andrea. She may be one of the most “classical” dressers I follow. A lot of her pieces are trend-adverse and probably re-sellable. But you can tell she doesn’t shop that way. And she doesn’t dress to have pictures that will always look “timeless.” She loves a risk.

Chanel ballet flat. But the color you love. Not the tan.

Will this image with the black The Row Patty boots look dated at some point more than a flat would? Inevitably!

Like many of those who consider ourselves what Tibi terms “CP” - creative pragmatists, some version of “classic” is part of my style DNA. This is the part of me that craves to emulate my dad’s style. Heritage pieces: the button-up shirt, the polo, the loafers, the khakis, the men’s leather belts, the cashmere crewnecks. But also for the CPs among us, you crave “modern.” It’s the modernity that turns these classics on their ear and keeps us from looking too safe, too lady, too expected. This tension is where the freshness lies. And yet what makes modernity work so well against “classic” is also what makes it subject to datedness!

I pulled up a couple more “classic” outfits I’ve put on lately. And in each of them, what makes them interesting to me will also make them dated.

This photo would appeal to more people and look better in 20 years in a photo album if I’d chosen a ballet flat.

And this one. If it were more “normal” - a less cray sleeve, a Chanel ballet flat, it would have a lot more longevity. And be a lot less me.

I see a lot of people who might think of themselves as having “timeless style” or “classic style” and I find them much harder to follow than those whose style is FAR more “out there” and much more unrelated to my own - but who bring interesting ideas to the table. Those ideas I can adapt to what I love and how I live, and they make me think and help me know someone. When I see someone dressed in all classic pieces, they may really, really know themselves — or they may just be trying to appeal to the most people. I don’t know. If it’s the former, I imagine there’s great satisfaction in it, and it’s just not for me. If it’s the latter, that’s too bad.

I think we all owe a debt of gratitude to the renegades of non-investment dressing. Those out there, wild risk takers whose ideas seem nuts at first, push us, and ultimately have us going: “of course!” Red socks, sneakers with dress pants, that looped through belt — all of it brought to you by people who 10000% don’t care if their style is “timeless.”

Look, I do understand why we might use the term “investment dressing,” and why we might be scared to buy what we really love as fashion prices become more and more astronomical. And I think it’s smart to consider quality and circularity and to shop in a thoughtful way, considering and reconsidering, especially given those prices. If you’re aware about it, and “investment dressing” is a shorthand for considering each piece and what it will really deliver for you, that’s one thing. But the thing not to ignore in the calculus is our true heart. I can’t imagine anything better to invest in than that. Even if it means recouping less down the road. I’ve regretted those heart overrides more than even the odd, unused purchase that helped me know who I am.