The Ones That Got Away // My Biggest Fashion Regrets

It was my first designer handbag purchase. It was too much money for me to pay retail for, so I stalked eBay auctions, learned all about authenticating designer bags, and read up on verified sellers.

Photos by Megan of Diary of This Girl and Ana of Northwest Blonde

I paid $350, or maybe it was $450, for my first (and at present, only) Louis Vuitton. I was 16 and was using one of my first tax returns ever on a Speedy 25, a bag I thought I’d keep forever.

Only, forever didn’t exactly happen.

A few years later, while in college, I decided to sell that bag. Why? I didn’t like the weird looks and attention the bag garnered. Instead of people appreciating my great fashion sense (which, honestly at the time that thought is pretty laughable), I’d get questions about where I bought that, or people would say things like, “Is that even real?!”

So, sick of people making eye contact with my bag instead of me, I decided I was over it. I listed it on eBay, and sold it at a loss. The patina on the handles had grown darker, the corners were a bit softer, and the market for Louis Vuitton Speedy bags was a bit oversaturated. Nevertheless, I let it go.

Now, almost 15 years later, I still miss that bag and regret selling it. It’s probably my most memorable fashion regret, but I have others too.

Like a leopard print coat from one of the first ever Target designer collaborations with Rodarte, back when it was called Go International. My mom warned me I’d regret getting rid of it, but I sold it on eBay anyway. I probably only made about $30 on the sale after all of the eBay and PayPal fees, but I thought I was making a killing.

Or a long metallic maxi, bought on sale from Piperlime (anyone remember that store?!) for just $15. It was a style ahead of it’s time, with its pleated skirt and deep neckline. But I loved it yet had no place to wear it… so it was donated before I had a chance to take it out on the town.

Later, a vintage, knee-length red wool skirt I found at a thrift shop in Pullman during my college years. It’s a-line fit and bold color meant that it stood out a bit, but in the best way possible. And while I wore it a bunch, it somehow got discarded at some point post-college. Hopefully it’s being worn and twirled in by someone new.

And later, a tunic with colorful embroidery that I thrifted on a break from college, not much unlike this dress I recently purchased from Urban Exchange in Tacoma. While I may have given up on that tunic too soon, it ended up with me finding something recently that I loved even more.

While these regrets aren’t exactly earth-shattering, it does make me wonder the impact of cleaning out my closet with a bit too much haste. I’ve learned that sometimes, clothing just needs a break from my wardrobe… but perhaps it doesn’t need to be eliminated forever. Now, instead of discarding pieces immediately after cleaning out my closet, they go into a sort of limbo box, where they stay until the next season. Then, I reassess in that time whether or not I really think I’m ready to part with them (unless, of course, they just plain don’t fit, are damaged, or are otherwise unsuitable for my life.)

Does this make me a hoarder? Well, maybe. But, after learning the hard way a few too many times, my donations linger in the house a bit longer. The memories of the clothes fade, and when I realized that I forgot that such a piece ever existed in my wardrobe, it’s time for it to find its new home.

Fashion regrets: we all have them, whether it was a style we should have never worn or a piece we gave away too soon. What are yours? I’d love to hear about them in the comments!

9 thoughts on “The Ones That Got Away // My Biggest Fashion Regrets

    1. Jenn Post author

      Oh what an amazing find, and so sad you don’t have it anymore! :(
      I do love that there’s a resurgence of the Dior Saddle again this season and have been contemplating seeking out a vintage one.

  1. Allison

    This sit with me on so many levels. First of all… Always listen to Mom. Right?? She’s always right when it comes to clothes. There are some items of hers I’ve stolen over the past few years because they were high quality and she actually kept them. I went through a period in my life where I didn’t have a lot of money and therefore a lot of items went up on ebay. MANY I regret and can’t ever get back. Including a 2000s Kate Spade bag that my beloved Auntie gave me and she’s no longer with us. Items like those are sentimental and I would honestly still rock it today, if I had it. Love this post! xo

    Allison |

    1. Jenn Post author

      Seriously. Mothers always do seem to know best.

      And thanks Allison – I’m glad you could relate, even if that means some of our precious memories made their way to eBay over the years. I was always tempted for the “next best thing” and in retrospect, wish I hadn’t! Live and learn, and hopefully don’t make many of those mistakes again. <3

  2. Camille Brown

    I find that, sometimes, it’s better for me to hang on to something that fits me WELL, even if the style is not the current trend. When it fits just right (and provided it’s not downright tacky), it IS just right! And regarding designer handbags, I’ve never really had one of the crazy expensive ones, but your comment struck a chord that I’ve never thought about: if I DID ever get one, I most certainly would not want the bag to become a coveted focal point, you know? Good old-fashioned conversation, especially in light of all the electronic distractions in our lives, is hard to come by, and it certainly doesn’t need one more thing diverting it from topics that are truly meaningful, you know? :)


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