Investing with No Return

Shopping, I love you, but you’re bringing me down.


I fell in love with Leonardo DiCaprio in 1997. Titanic had just come out and frankly, there was no reason why he and I shouldn’t have been together. But minor details like an age gap, my being in middle school and his being Leonardo DiCaprio, and geographic handicaps (I lived on earth, he lived in Hollywood) kept us apart. For months, I printed and reprinted images of Leo and plastered them to my walls. I’d kiss them before I went to bed and think long and hard about how beautiful it’d be once we met and my end of our love finally went requited.

“You’re the one,” he’d tell me.

“I know,” I’d agree.

And then we’d live happily ever after on land and never take a boat to get anywhere.

The thing is, I saw and met him two years after I’d initially fallen in love but it was nothing like it should have been. Sure, he smiled. Obviously I smiled back. But there were no butterflies or fireworks, and the magnified figment I’d conjured using my imagination was just that: a figment of my imagination.

When considering fashion, shopping, and trying to locate the perfect “Investment Piece,” I am almost always reminded of that very moment and the Romantic Dalliance That Never Could Have Been.

Who is the evil genius who beguilingly manipulated an entire legion of consumers to believe that they could actually “invest” in clothing and the accoutrements that come with them? I’m asking because I’d like to stab him with the $495 white patent leather boots I idiotically bought two years ago but have yet to wear once.

“These are forever,” the salesman told me. “The designer remakes them every season.”

“I think you’re right,” I complied.

He was right — they are remade every season but the fact still remains: I haven’t worn them once.

To be fair, it’s not entirely the manipulator’s fault. We are, after all, a mass of shoppers who have unwittingly tricked ourselves to believe that clothing is a reasonable investment. That we should want to buy things that will last forever because then we’ll want to wear them forever has become a curious, albeit deceitful norm among the denizens of department stores but we should know better by now.

Have you ever purchased something that you said you’d wear forever? Probably. How long does “forever” actually last, though? If I’m being really generous, I’d give the perpetually-wearable piece in question three years before it’s rendered absolutely futile.

We are humans, we crave change. So what gives with the allure of acquiring a sartorial stock? I guess before we can answer, we should break down the two types of investment pieces that most women look for.

First, there is the Tim Gunn-approved French rule of five that mandates you actually purchase “timeless” sartifacts (sartorial artifacts): a black purse, tonal pumps, a trench coat, etc. Then there are the items, like the mohair and printed in an almost-pastel, highly graphic, oversized plaid sweater that has elicited my writing this story, that we disguise as investments to help make appeasing our indulgences slightly more digestible. In the case of my sweater, no one will knock it off well enough to satiate the hankering. The thing is, when I learned that it retailed for a steep $1,200, I had to rethink how deeply I was willing to, you know, invest.

I tried to calculate cost-per-wear to justify spending upward of a baseline four-figures but that was a fruitless undertaking. I told myself that the designer knows what she’s doing and that I must be missing the big picture, but this didn’t make it any easier on my funds. I even tried to convince myself that I’d be able to wear the sweater forever and that’s when I got frustrated.

Why can’t I just want the damn sweater without having to feel like I must justify my propensity for it anyway? Wanting and getting are two fundamentally different things. I suppose I fear that my judgement regarding that which I think I should have versus that which should remain a want (like a celebrity crush), has become spectacularly clouded by a constant, nagging urgency to feel like everything I own, I should want to own forever.

There is, of course, an argument to be made that some pieces do get passed down and remain special forever, but in our generation of buy fast, have now, think later, how important are these items? Whether at H&M or Hermès or in the case of one pair of white patent leather boots, if we fall from the second camp of investors, there’s no way we’re not just masquerading indulgences to make them feel worth their splurge. The problem is, like my relationship with Mr. DiCaprio, sometimes these things really are best left loitering in the inflated trenches of our imaginations.

Get more Shopping ?
  • (BAD) Blog About Design

    An investment piece does not have to cost four figueres. Cost does not always translate to quality. Love the story! Thanks Leandra.

    Check out the BAD blog…

  • I have a closet full of things that I had to have and have never worn this is the marketing genius of the fashion industry. I have a friend who has fallen in love with the Michelle Williams Vuitton ad campaign so much so she had her hair cut to match and purchased the bag!

    • anonymous

      Well I tried to copy her make up from this campaign XD

  • Hereshoping Themayanswereright

    Problem is things I want give more of an adrenaline rush when purchasing, so there is a bigger (emotional?) payoff than getting a “should” item. Some people have more self control and are able to keep it “loitering in the imagination” and be fine. Unfortunately for me, loitering in the imagination, quickly turns to obsession, which turns to the one that got away, which is really hard to take. I’ve sadly had a 3 year saved search on ebay for an item I saw too late and was sold out in my size. I *still* have issues with that one getting away, still think about it and pathetically hold out hope that someone will give theirs up and finally it will be mine.

    • Leandra Medine

      This is such a true and interesting point and totally speaks to the latter kind of investing. I got over the sweater, ultimately but I myself just fell victim to the plague again with a pair of Prada sandals as evidenced by every single one of my social outlets. I tried to own the shoes socially hoping it would make not owning them IRL considerably easier and but guess what? It didn’t. The thing is, they’re definitely not as romantic but when they tangibly belong to me. And sooner or later (please heaven, later) the next OMG I MUST HAVE YOU item quietly sneaks in et voila, we’re back at square A. I think people liken shopping to hunger because even after you satiate a craving and curb your appetite, it comes back. There’s no avoiding it.

      This just in: my stories are actually cathartic, confessionals

      • Hereshoping Themayanswereright

        Hehe that is so relateable..good to hear you’re in the same boat with the never ending “OMG I must have you”’s such a slippery slope. The hunger analogy is SO accurate, for me it might even go further into a drug like effect from purchasing the “wants”. This huge endorphin rush, mood enhancement and energy boost, that consistently overwhelms my better judgement and budget:-(

  • Sarah

    This is so true. I get sick of wearing things a long time before they physically wear out.

  • Brie

    Me too. Except we really do belong together. Since that first moment I saw him on Growing Pains, I knew it in my heart. I love you Leo.

    • Charlotte Fassler

      Preach, girl.

  • Reminds me of the time I purchased a Rapunzel-esque Anna Sui dress from the Fall 2008 show that was an impulse buy and never wore it. Like everything else in the store, I convinced myself I needed it. I love that store, but it really has a way of mesmerizing you and making you lose self-control.

    Just realized, I should take full responsibility for my lack of self-control instead of blaming the store.

  • I’ve been thinking about this a LOT lately. It’s no secret the majority of my disposable income goes towards clothing, after all, I work in fashion! (And there I go with another justification of my ridiculous spending.) I was recently debating the purchase of a new Chanel bag, a classic flap but in a fun, punchy statement color — it’s a TRUE classic. But I realized that I could literally spend the same amount of money and go on a week long vacation to Europe with my girlfriend, and pay for everything for both of us. When I consider things in that perspective, Chanel loses. For now, I’m choosing to invest my disposable income more so in experiences. I’ll only be 27 once, but Chanel will be there forever.

    • eye4style

      Investing in experiences always pays back in dividends!

      • Couldn’t agree more! As “they” say, travel and experience are among the few things that actually make you richer.

    • Charlotte Fassler

      I have recently changed the types of investments I make and totally empathize with your decision. There is something to be said for spending your hard earned $$z on an experience versus a tangible item. Every trip to Europe I have saved for has been an unbelievably rewarding use of money and I am happy to be able to have ownership of that time even if it was a fleeting week and not a bag that I can pass down.
      I will say though, there are some articles of clothing and accessories that are representative of specific experiences I have had while wearing them so they can sometimes be both an experience and a tangible object depending on how you look at it.

      • Oh, for SURE!! Certain tangible items are an experience in and of themselves. But if I’m just buying to buy? I can wait, especially when it’s an either-or situation.

    • Alyssa Beltempo

      Your last thought brings up a point which I have been internally repeating this season. The amazing thing about fashion is that there will ALWAYS be something newer, cooler, or whatever-er in the seasons to come. And those “classic” pieces will ALWAYS be around because, well, they’re classics. So if there’s an item that I can’t afford now for whatever reason, I try to comfort myself with the thought that the world of fashion’s offerings will still be my proverbial oyster when I’m financially ready. Except in the case of vintage. Which is always a free pass and another topic entirely.

    • Thamsa

      this is an excellent philosophy nicolette! I hope you did take that weekend vacation 😉

    • Jenny

      I have been scolded by my friend – mind you her head’s very high up above fuhshun. I’ve wanted a Celine bag/Balenciaga cutout boots and my reason was they’re investment pieces, but I’ve never spent so much on a single product so I’m quite scared of how that’ll feel once the return-by date has passed. *Then again eBay is there for a reason.*
      Cue in my friend, “I’d never buy a shoe or bag for that price, i’d rather go on holiday.” But then the difference is that I would, and I don’t see anything wrong with it – my only restriction is the guilt that keep haunting me, the exact buyers guilt this post discusses, that maybe after the novelty wears off I’ll feel like I’ve wasted my money. And then here’s the other thing, unlike my friend, I’m not fussed about spending that money going on holiday, and I’ll be totally happy. And like you’re saying, for me, Paris or Milan will always be there…but come in two-three years, maybe the Balenciaga boots or Celine trapeze will be the one that got away?

      I guess there’s no doctrine to investment pieces, it’s a matter of personal lifestyle and your own priorities?

    • Mckenzie

      Where do I shop if I’m not rich

  • Alyssaspeaks

    I agree. Plus shopping for real investment pieces (the Tim Gunn-approved ones) can be terribly boring. I love shopping, but there are those things I KNOW I need and will wear to death (like plain black leather pumps suitable for the office) that make me actually dread shopping.

    I much rather buy whatever looks cute/cool/kooky/gorgeous/amazing no matter how impractical/expensive/one-season-only it really is.

  • seresy

    I have FIVE LV Noes, in various colors and sizes. They actually do last forever, and I do buy them secondhand/vintage, but who needs five of the same bag? Also, they’re just drawstring sacks. I love them (obviously) but keep grabbing other bags to use instead because I’ve already spent years with them.

    I figure I’ll come back to them when I get the urge and will fall back in love, but for now they’re pretty pretty decorations that should really be used. And then I get “I spent a fortune on these” guilt.


  • L

    I think we project a lot onto the things that “got away.” We think that by owning them our lives would have been different and somehow more perfect. But when we get those things, nothing has really changed. So we move onto the next item and hope that it will be the one to “change things.” All we are left with are some great items in our instagrams.

  • Ha! Should’ve made a go at it like Kelly Oxford and try your hand at hunting Leo…just like what I do with certain “investment pieces.”

    Your Friend, Jess

  • I totally understand this. I have been craving the sweater as well, but the more I see it on the models and people the more I think it really doesn’t look that great.

  • CDJ

    I 100% went through this with my RAZR scooter (color: red).

  • mmaexetoile

    If I ever have a tinge of doubt about something, I don’t buy it. I really try to invest in those pieces I can’t stop thinking about… and most of the time it’s shoes. And the commenter below is accurate- cost doesn’t translate into quality! That’s why thrifting is such a wonderful way to “shop” because every thing has been used at least once, is inexpensive, and has stood the test of time!

  • Brigita Dambe

    The thing with investing is that you will eventually get sick of those pieces. And even if you invest in those must-have pieces like a trench, perfect white t-shirt, amazing jeans (at least they say you should, and that is what makes you buy them), in reality you might not even wear them once. Like it happened with your white patent leather boots! I haven’t worn jeans in seven years and bought my first white, ok, black t-shirt, that supposedly everyone should have, and I can’t find an outfit I would wear that would incorporate the said t-shirt.

    What I’m trying say apart from that everyone has to have must have pieces that go with their style, is that it is hard to not to be under pressure and not buy that damn t-shirt!

    Thanks for sharing this! Put everything in perspective!


    • taylor

      You might get sick of them, but I think it’s totally natural for that to happen when it comes to investment pieces (if you truly plan to have them forever)! I have this one navy blue wool cardigan that I purchased five or so years ago but went through an anti-blue phase for a couple years and never wore it. I knew I’d eventually get over that phase though, and sure enough, I can’t wait to wear it this winter.

  • Amatoria Clothing

    I agree that it is a problem to have the urge to buy things all the time when they are very expensive, because it leads to you being broke.

    My bigger problem is with the urge to buy new clothes all the time just because something is a “trend”. These items are often bought from lower-quality stores, which means you DEFINITELY will not want to wear that again in a couple of months.

    “…there’s a growing public consensus that the mass production of so much cheap clothing is an enormous waste of resources such as fuel and water. While many people donate their clothing to charities and consignment shops, fast fashion tends to be so cheaply made that no one wants to buy it, she notes. Instead, it gets recycled into industrial rags and insulation, or even thrown out altogether — generating the term “landfill fashion.”

  • giselaandzoe

    My investment pieces goes a little something like this, I wait for sales and cross my fingers it still there. Sometimes it is and it feels so good to buy within my budget!

    • Claire

      i’m so with you on this one!

  • Katie

    I am one that has always loved that “instant gratification” of pushing the buy button on eBay and getting what I wanted but my bank account and credit card hate me for it. Maybe its our generation being born in the 80s and 90s- not experiencing a depression and saving everything or making it ourselves. As a historian I also find this fascinating.

    I had success though on eBay tracking down a pair of 2009 Bruno Frisoni tan wedge booties that I was dying for after I saw them in a magazine.I waited and waited and waited until they were there and checked at least once a week and I stuck oil! It worked and for way less than their original $1200 price tag.

    I regret having spent so much on Isabel Marant when I could have easily bought a trip to Europe… I feel like my investment in Celine was a worthwhile one.Certain designers are important not to miss out on if they only design for a brand for a short time. Thoughts?

    • Thamsa

      I am usually the type of person who will visit the same store five times to contemplate an item. I know that I really like it, but my previous disappointments often make me really consider an item, how it feels, how comfortable it is etc…

  • AshleyOlivia

    When I’m shopping, I never think in terms of “investment piece”… I think, how will this fit into the (very opinionated and unique) environment that is my closet? Will this jacket play nice with my collection of pants? Will these boots be comfortable getting to know my collection of jegging cords? In more prosaic terms, does this piece look like ME? I don’t buy pieces that are so trendy they won’t work three seasons from now (hates you neon), and I’ve really defined my own aesthetic at this point. This past summer I ruthlessly slashed and burned my closet, which was full of things that no longer fit or I’d purchased on sale because hey, it’s on sale! Even more prevalent were pieces my mom bought for me that I’d never liked (my appreciation for the gesture still remains, even if the offending garment is gone). I can honestly say that everything in my closet is something I absolutely, positively, genuinely l-u-v and by evaluating new pieces in terms of whether or not they work with the items I already own, I’m better able to decide if it is something I will enjoy wearing in the future or will just generate buyer’s regret.

    I also try to only purchase items that are well-made, but within my own budget expectations.

  • I own two closets full of clothes and I don’t think I have even worn half of the first one. But the thing is that when it comes to shopping, we just don’t think rationally; we fall in love with the garment, we get this momentary ‘extreme happiness’ feeling and we just feel the need to purchase it regardless of the price, ignoring that little voice in our head whispering that we will never wear that. What else can you expect from a consumerist society?

  • Thamsa

    I think if you want something but each time have an internal struggle with yourself, justifying the reasons, deep down you know it’s just something frivolous. Now, I’m not saying that every item you own should be well thought out and should be an investment piece, but it’s important that you love it (at least, these things are important to me) I just have to ask myself, will I wear this anywhere outside of the change room, if I even have to contemplate that question, I know the answer is no. It took me a long time to get to that point.

    I started to think more about my purchasing habits a few years ago, after reading the excerpt of an article “Secrets of French Girls” by Ellen Wallace written back in 1982 lol :

  • Andrew

    The Balenciaga cut-out boots. $1275 of pure impeccable fabulousness. But instead of doing something logical, like just realizing that I can’t afford them, I became full of drive. There was nothing stopping me from having them, and they were going to be mine whether the credit cards companies were okay with that or not. But during all of this time of thinking up different strategies (“I’ll steal them from Bryan Boy’s apartment”, “no Starbucks for the next 6 years, great idea!”), they became sold out in my size. And only afterwards am I able to wonder about whether these boots were really worth all the shit I was going to do for them.
    I’m undecided.

  • Pilar

    Me encanta DiCaprio ,es la caña de guapo .
    Un beso

  • gloria

    I try to only buy things that are good quality and made in the USA (I’d stray to European-made too: I do love my Chanel and Celine bags). It’s better for the environment because it’s less waste (no fast fashion for me EVER) and less of a carbon footprint. As I get older, I realize that quality stuff just makes me happier. I know not everyone can afford a $400 dress, but I’d rather have one beautiful garment than a lot of junk that is made in Bangladesh/India. I want to support artisans and people skilled in their craft. I want to give money to people making things in America and delivering goods that they know is beautiful and will last. I like craftsmanship. It’s crazy to me because when I make jewelry (gold is VERY expensive now, I know), people don’t want to spend $500 on a bracelet. These same people will buy shoes for $200 at a chain store that cost $30 in China to make. My costs are high because I do everything here by hand and I use a quality material. It’s important to think about how we consume and why. I choose to consume goods that support my personality and my values.

  • malky W.

    I could relate so much to this post. I’ve definitely had incarnations of those “white patent leather boots”-things that I bought in the heat of the moment and I was so sure they would become my favorite pieces because I had read of their praises in magazines, e-tailers and salespeople “suggested” them special for me or lauded them as an “investment-piece ” or a hero piece; then I never wore them or I wore ’em once (An orange and blue floral Michael Von der ham skirt, hot pink patent leather Nicholas Kirkwood smoking slippers, purple bedazzled cateye glasses…. ) And now when I look at those things I have so much buyer’s remorse. But even after all of those regretful purchases a glossy photoshoot or a cliched line about something being a “must-have” still it gets me every time…I’m a sucker for a good sell.

  • Sarah Fentem

    the thing is, as a 20-something creative type, how often am i going to wear “investment pieces” like black dry-clean-only trousers and fancy pumps? A real investment is something you’re going to wear EVERY DAY that WORKS and LASTS. Investment pieces for young people (rad sneakers, leather jackets, bitchin jeans) are COMPLETELY different from investment pieces for the mom-aged. I can’t wear a Burberry Trench while I’m bumming around on my bicycle because grease will get all over the back of it. Not practical.

    Like someone mentioned, I think a lot of the logic lurking behind the “top ten items stylish ladies need” is largely a result of advertisers pushing their most expensive products. Even the best sneakers cost way less than a pair of mid-level pumps from a brand like Jean-Michael Cazabat, so they’re going to say that’s what we need. Same goes for a trench coat, black dress, etc.

    The best investment pieces I’ve ever got are my Frye Harness 8rs, my St. James stripey top and my j.crew mens’ brown leather jeans belt from 2003. I have a LV doctors satchel that never gets any use because it is silly for my lifestyle.

    • Poulette

      This is spot on – its pieces that work within your life, not generic investment pieces because Tim Gunn said so. Working freelance has meant my current “investment” pieces are more likely to be a pair of fabulous house slippers, kick ass jeans or turban to hide my unwashed hair (and to scare the neighbors dog).

      • Sarah Fentem


  • Maria

    Investment pieces have to be expensive for two obvious reasons. 1. If you get, say a cheap trench at Zara or HM or Topshop it wil eventually be discarded when the shape becomes outdated…(too long, too short, too wide, too minimal, not the right lapel etc….) if you spent the”right” ammount of money; it has to hurt a little bit, you will hang on to the piece for ever and it will charmingly work when the shape is outdated…. Say good making, say old charm, perfect wear off… 2.If the piece is good quality it will literally last for at least 15 years..

  • Amanda

    Love this, love the relatable aspect of your writing. I have found that I am never as persuasive as when I am talking myself into purchasing something that I “deserve.”

  • Rebecca

    No, I think it’s good to justify and question your purchase. Apparently the Celine checked pieces are a little less expensive! x

  • I believe that there is a bit of smart behind “investing” in pieces that you would deem closet staples. As you said, the Tim Gunn 5. Blazers, great pumps, white button downs. Items that are truly the “boring” and canvas pieces of your closet but get worn daily. A good handbag is something I believe spending a good amount of money on; however, I have yet to buy a designer handbag at full price. I live in a market where no body knows nor cares if I have last seasons design. So, I settle for Marshalls or TJ Maxx to curb my Designer Itch

    xo, Nina

  • Celine

    Why not wait until it’s on sale, or until someone has a closet-clear out and for some reason, sells it (who knows, it might happpen) – it will be a lot cheaper, and if it really is a staple or a must-have, then it should be good any season/year, no?

    • Leandra Medine

      My no good ex boyfriend IMPULSE always gets in the way rationality as mused by you. You are certainly right, though

  • Greer Clarke

    Was the point of this entire article just to #humblebrag that you met Leo?

  • Caroline Y

    Having bought so many items that I then did not wear I have developed a strategy:
    1. I have organized my clothes by color making me more aware of all the similar (and often black) items I already own. This stops me from buying the same items, e.g yet another black jacket. 2. I have put a small coatrack in my bedroom where I put my outfits for the working week. This makes me vary my choices more but also made me realize that there only few outfits that I truly love. And again: how many nice clothes I already have and hardly ever wear… 3. When I try a nice item iin a shop I ask myself: Do I already own something similar? Is this nicer than what I am wearing today? Would I feel sad if somebody else would buy it and it would not be available anymore? Can I afford it? Is it reasonably priced in relation to its quality /uniqueness? I buy it if the answers are: no, yes, yes, yes, yes… 4. In case of doubt I photograph myself in the clothes-item. I can then better and more unbiased check if it looks good on me and even ask friends for their advice. 5. When I have bought the item and hardly not think / care about it, or it does not fit with the rest of my wardrobe I return it. (Still unworn, of course)

  • Jonesing now

    Good post. The crazy thing is my love of the item dissipates drastically once I have it. It’s like depreciation on a new car!

    Three things I do to satisfy the craving for buying something new- 1. Shop my closet/have a try on party in my house and rediscover half the stuff I’ve forgotten. 2. Shop at thrift stores…real thrift stores not expensive consignment. It’s REALLY a thrill to get great unique pieces for next to nothing (just don’t get in the trap of buying junk). Only get truly remarkable things, or 3. Cut out from magazines and create a look book

  • Courtney

    Ugh, hear hear Man Repeller. In fact, the only items of clothing that are worth investing in are the boring ones- the black goes-with-everything bag, a sturdy but pretty bra, and perfect pair of jeans.

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  • tunie

    When you’re hungry, don’t shop for ANYTHING, according to this Smithsonian article, lol:

  • Martine

    Its not the one expensive piece that troubles me. Its the buying practically a new wardrobe every year thta seems disgusting. Clothing should be an addition. Not a constant replacement.