The Designer Pieces I Regret Buying

I’ll admit it, I’ve spent rather carelessly in my life. My splurges have run the gamut from trendy pieces I bought for the sake of having something new to timeless designer pieces that, while almost always bought at a steep discount, were still too expensive.

For the record, I have mostly reformed. I no longer shop with reckless abandon. Sure, I buy pieces when it’s not totally necessary, but I don’t make impulse purchases to bandage a bad day. I’ve developed a keen sense for what I feel most comfortable in and I thoughtfully mull over items before even clicking add to cart. While I essentially online shop for a living, I’m rarely tempted day in and day out to give in to the items I feature. This is all well and good. Impressive, some might say. And yet, I recently bought a handful of what I thought would be forever pieces, and I’ve already realized I don’t like some of them, or I’ve grown tired of them or even worse, they don’t fit me (and aren’t even salvageable by a tailor). Oof.

Backing up a bit, the first designer item I ever bought and later regretted was a pair of Christian Louboutin stilettos as a college graduation gift to myself (on the brink of moving to New York City to begin an unpaid internship, they were clearly a wise choice). I had my heart set on the red soles, which are absolutely classic. The regrettable part is that I ordered them online without having ever tried them on in person, and lo and behold, they were too small. Determined to make them work, I teetered around in the egregiously high platforms a few times before coming to the realization that they were a total wash—the height was so impractical and my toes were scrunched to a merciless degree. They had to be resold. I made some money back, but not enough. This should have been my lesson.

But years later and a uniform of sorts in play most days, a few of my recent designer purchases are plaguing me. I bought a Gucci bag for the first time (fashion-girl gold!)—an ivory quilted cross-body camera, which, while very fun, I instinctively knew was not my typical shape. I really wanted the shoulder bag in a more timeless shade like red or black, but it was a lot more expensive and the ivory felt more now. My boss even told me that while it was super cool, I would likely tire of it and damn it, here we are.

Then I had a couple episodes in which I hit the summer sales and sample sales a little too hard. In the moment, I was making smart decisions—selecting a few fun yet practical pieces to add to my mix of basics—tops and dresses, a black linen blazer, midi skirts (my kryptonite) and most recently, a pair of scrunched leather Isabel Marant boots for fall. They’re fab, really, and in black they’re incredibly versatile. They were a lot though, and honestly, I walk a bit clunky in them, which is unfortunate.

While in theory I do mostly enjoy these pieces, I shouldn’t have spent the money. Worse, incorrect sizing got the better of me once more—the idea that I was getting a great deal overcame me and one size up or down didn’t seem that big an issue. How could I go wrong with a slightly oversize black blazer? Well, I’m swimming in it and look ridiculous. At this point, most of the pieces have lost their luster and I ultimately wish I had refrained in the first place.

The real reason I’ve ended up in this situation is the notion that I need to break my mold and enliven my routine. I’m surrounded by well-dressed women every day, many of whom have gorgeous and often expensive accoutrements I might add, so to see myself in a T-shirt or with an unexciting carryall most days makes me feel a little well, blah. But truthfully, I’ve already taught myself this lesson—I am most comfortable in simple things. Sure, well-made versions of classics feel better and last longer, or those with a flicker of trend-wise detail can feel right. Most importantly I need to make sure I’m buying appropriate sizes—trying things on in person or committing to a return if it’s an ill fit—and only indulging in special pieces that are truly classics. I know myself, and It items are just not my bag (pun intended), so if I dabble in trends, affordable is the way to go. It’s called timeless for a reason, and well, that’s me. I can dig it.

Feel similarly? Shop some my classic fall picks ahead.

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It's Not Always Worth Buying Designer