My Wardrobe, Myself

The intersection of clothing, emotions, and life

My last four posts looked at the oldest items in my wardrobe and why they have been in my closet for five years or longer. There were 79 such pieces, and many of them are still worn on repeat today. In my last essay, I shared that the most common features these garments, shoes, and purses have in common are a consistent color palette and classic styles and silhouettes. Additionally, the majority of them were purchased new rather than secondhand, although nine of my “oldies but goodies” were bought in resale stores.

Today I’m going to look at the flip side of the equation, the pieces that did not stand the test of time in my wardrobe. In addition to the 79 items that I covered in my last series, I also purchased a lot of other clothes, shoes, and bags that left my closet a long time ago. While some of what was passed on was due to “wear and tear,” that wasn’t my reason for letting go of many other items. However, as I went through my folders of what I purchased in 2018 and earlier years, I discovered some clear patterns regarding what didn’t stick around. I’ll share those patterns below, along with photos of many of my castoffs (some of which fit into more than one mistake category).

clothes that didn't stand the test of time

Which of YOUR closet items have NOT stood the test of time – and why?

Bad Resale Buys

I first got into resale shopping about twenty years ago, and I remained a secondhand enthusiast until the pandemic hit in 2020, although I had slowed things down quite a bit in the few years leading up to that. I loved “the thrill of the hunt” inherent in that type of shopping, and it was fun to find hidden gems in thrift and consignment stores. I had to stop secondhand shopping due to my increasing chemical sensitivities, but I also came to understand how unsuccessful resale buys were for me. I’ve acquired some “winners” along the way for sure, but my overall success percentage with thrift and consignment shopping is very low.

Below is a look at the resale purchases I made between 2012 and 2018 that were “duds.” I’ll be covering many of them in subsequent sections in terms of why they didn’t stand the test of time for me, but that might be obvious to those who’ve been following me for a while. Even a quick glance at the thumbnail images will reveal a sharp contrast to the “oldies but goodies” shown in my last post.

purged items: bad resale buys

Shopping resale can be much like buying from the clearance rack. The prices are low, so we’re more likely to compromise or settle when it comes to item characteristics that are important to us. We may love the color but little else, or we may love everything but the color, but would we pay full-price for those types of items? Usually, the answer is no, so we shouldn’t purchase them at clearance or resale prices, either.

Unfortunately, it took me a very long time to learn from my resale mistakes. I kept looking at items in secondhand stores with rose-colored glasses, imagining what they could be instead of seeing clearly what they actually were. Sadly, I often compounded my mistakes by spending money to alter ill-advised pieces, and sometimes those alterations were risky to boot. I’d sometimes purchase a garment that was a size or two too large, believing that it would be “easy” to tailor it down to fit me. I was often wrong…

I cringe when I think of the money I’ve wasted on bad resale buys, but I did eventually learn. I now realize that I’m not going to like something any better because it was “a deal.” When I go to wear an item, it matters very little how much it cost. I either like it or I don’t, and I either feel comfortable wearing it or I don’t. Some of the pieces shown above were worn multiple times, but I never loved any of them. They should have never come home with me!

Bad Colors

I haven’t always known which colors look best on me, so I used to make a lot of missteps in that area when I shopped. I have a cool-toned complexion, so I look best in cool-toned colors. I don’t look good in beige, brown, yellow, and orange. I also can’t wear many shades of green well, and stark white tends to wash me out. I often like these colors on other women, but they don’t work for me at all.

Here are some examples of items that I purchased five-plus years ago that were in hues that are a bad match for my personal coloring:

purged items: bad colors

Many of the above pieces were bought either on sale or at a resale store, but some were purchased retail at full-price. I just didn’t realize that they would make me look washed-out or ill, but they certainly did have that effect! I wore the coral knit blazer multiple times, but it was always too bright and warm-toned for me. I also wore the green and gray striped tee at least a few times, but I never felt good in it. I now have a much better understanding of my best colors, so I don’t even consider anything in the shades displayed here.

Gray Items

I could have included gray items in the “bad color” section above, but I thought they merited a separate mention. I’ve often heard style experts say that wearing clothes and accessories in the color of our hair is a good way to go. My hair color is now in the gray family (although there is still a lot of my natural light brown in the mix), but gray looks worse on me now than when I was dyeing my hair. The items below were purchased both when I had dyed auburn hair and when I was going through my (seemingly interminable) gray hair transition, but they didn’t work for me at either time.

purged items: gray items

Gray clothing almost always makes me look tired and washed out. Sometimes there’s a “unicorn” shade of gray that I can wear close to my face, but the versions of gray pictured above were not that. A lot of gray clothing is in the warm-toned family, like the color of an elephant, and that shade looks especially bad on me. I tried to “rescue” some of the pieces above by pairing them with printed scarves, but I ultimately decided to pass them on, and I now avoid gray clothing for the most part. Like with white, I can sometimes wear gray as part of a print (and I also own a burgundy and charcoal color-blocked top), but solid gray is a no-go for me.

“Busy” Prints

I like a good print, but I tend to prefer ones that are on the subdued side. Stripes are my favorite pattern, but I also enjoy polka dots, watercolor prints, space dye, hounds tooth, and some abstract prints. The prints below are all much too “loud” for my personal sensibilities. Even though some of these prints are grounded in my best colors like black, cobalt, navy, and purple, they’re just too “busy” for me.

purged items: "busy" prints

I think that I liked many of these patterns in theory or on other people, but they never felt right on me. If you’re familiar with “Dressing Your Truth,” most of these prints would be more suitable for a Type 3 “rich and dynamic” woman, whereas I’m a Type 4 “bold and striking” woman. I’m not a strict adherent of the DYT system, but I do find that it makes a lot of sense for my personal style aesthetic. When I wear the colors, patterns, styles, and silhouettes that are recommended for a Type 4 woman, I tend to feel much more emotionally comfortable in what I’m wearing, as well as true to my own nature and personality.


Ruffled items featured heavily among my purchases from the early 2010’s, but I found that I didn’t end up liking to wear them. The photo below shows the ruffled tops, cardigans, jackets, and skirt that I acquired during that time frame. These pieces were mostly bought at consignment stores, although a few retail purchases are in the mix as well (i.e., brown zebra tank and red cardigan).

purged items: ruffles

Most of the above items are in colors that work well for me, but the ruffles are too “romantic” and feminine for my personal style aesthetic. For some reason, these pieces appealed to me in the store, but when I wore them, something felt “off.” I don’t necessarily want to wear completely plain pieces, but there’s just too much going on in most of these ruffled items for me to feel like myself in them. The one top that I did wear a lot, though, was the cobalt tee with a ruffled neckline. I guess that was a subtle enough detail for me to not feel overwhelmed by the ruffles, but I honestly would have preferred a simple V-neck instead.

Bad Silhouette

Sometimes I like things in theory but not on me, which was the case for all the items shown below. The colors and patterns are all on point for me, but the silhouettes were problematic in some way. In many instances, I was trying to jump on board a current trend, but not all trends are a good match for our body shapes and personal sensibilities. Of course, not everything needs to be conventionally flattering, and if you love something you should be all means wear it, but these pieces just never felt right to me.

purged items: bad silhouette

The two dresses in the top row were too flared at the bottom for me, which I felt made me look more bottom-heavy than I already am. I sometimes like a slight A-line silhouette, but these dresses were too A-line for my preferences. The same was true for the denim skirt in the center of the photo. I wanted a denim skirt, but that wasn’t the right one for me. I would have been better off with a skirt with a straight silhouette or a small flare.

The other two dresses pictured (fuchsia and navy-striped) had different issues. The fuchsia dress had a blouson waist, which hid rather than highlighted my narrow torso. That made me look heavier than I was because it hid the smallest part of my body. The drop-waist navy-striped dress had the same effect. I think I would have been fine with the dress if it didn’t have the line towards the bottom. If it was just a relaxed fit dress without the drop-waist effect, it could have worked for me, as it was streamlined enough not to drown my figure.

The final three items in this grouping are the black bomber jacket, burgundy cardigan, and polka-dot tank. The bomber jacket was very well-made, but the boxy silhouette was all wrong for my hourglass figure. This style looks great on a lot of other women, but I feel “off” in anything that’s boxy and doesn’t highlight my smaller waist and torso in some way.

The length and flare at the bottom were what made the burgundy cardigan problematic. This was the original version of the Athleta Pranayama wrap, which has since been redesigned such that it’s much more flattering on my figure. I purchased the newer burgundy version of this style earlier this year and like it so much better. As for the polka-dot tank, the peplum hit me too high and the flare made my hips and bottom appear larger. I’ve actually never found a peplum style that works well for me, so I’ve given up on that silhouette completely. I’ll leave it for other women who wear it well.

Bad Length Pants

In the early 2000’s, I was a frequent wearer of Capri-style pants, as they were a popular style at the time. However, when I tried to wear this style more recently (early-to-mid-2010’s), I was less enamored with it. I found that the hemline tended to hit me at the “meatiest” part of my calves, which had a widening effect. Some of the pants shown below were probably supposed to be longer, but since I have very long legs and they weren’t tall sizes, they just weren’t long enough to be flattering.

purged items: bad length pants

Most of these pants were purchased retail rather than resale, but I wasn’t mindful enough of the length. I liked the styles and colors, but none of these pants ever worked well for me. I wore the black Metro Slouch Capris (top right) quite a few times, but I ultimately decided to pass on all my Capri-length pants.

I now much prefer an ankle-length style, as it’s much more flattering on my legs. I still must be careful of lengths, though, especially when a tall option is not available. But fortunately, I have a nice collection of cropped pants in my closet now, which I look forward to wearing again as soon as the temperatures warm up.

Curved Hems

If you’ve been reading for a while, you know that curved hems are not to my liking. In fact, I included this style feature on my list of “don’ts” that I published in late 2021. However, I didn’t yet realize how much I disliked this detail when I purchased the tops shown below:

purged items: curved hems

I think my disdain for curved hems may also be related to my height, as I find that the shorter part of the hem tends to hit at the widest part of my hips. If I were shorter, that probably wouldn’t be the case, and I do have two tall-sized waffle tops with curved hems that are more flattering on me (but still aren’t my favorites). I just prefer the “neatness” of a straight hem, and I like when the hem hits either a couple of inches above or below my widest part. I no longer purchase curved-hem items, but they are very prevalent in the retail landscape, so I must be relatively alone in my dislike of them…

Side Slit Tops

Side slits are another detail that’s common in tops and toppers but disliked by me. So many tees, blouses, sweaters, cardigans, and jackets feature side slits that range from an inch to six or more inches. The three sweaters below are examples of pieces that I purchased with side slits but didn’t hang on to for very long:

purged items: side slits

The lengths of the above tops were also problematic (see the next section), but I found the side slits both annoying and unflattering. Perhaps again it’s because I’m tall and have wider hips, but the slits never seemed to lie flat, and they also hit me in a bad place. I just find that slits in my hip region only serve to highlight that area, which isn’t something that I want to do. I prefer to play down my curvier hips rather than play them up.

I think that side slits may be better on women with apple, rectangle, or inverted-triangle shapes, as they may want to add more volume to their bottom halves or allow more room in the tummy area. I’m sure many women love side slits because they’re virtually everywhere, but I have been avoiding this detail for years now.


The three tops shown in the previous section were all tunic-length, and I purchased multiple other tunics in 2018 and earlier. The style of wearing tunics with skinny pants or leggings was all the rage for many years, so I added the tunics below to my closet during that timeframe:

purged items: tunics

Most of the above tunics weren’t worn often because I didn’t love the way they looked on me. I tried to wear them because they were popular, but they weren’t a good silhouette for my body. Again, they obscured my smaller mid-section, plus I never liked wearing skinny jeans or pants and I don’t wear leggings at all (I never have – I know I’m in the minority with this). Tunics don’t work with pants that aren’t very slim, so I never felt all that attractive in outfits that featured these types of tops. I much prefer a hip-length top (that hits at the high-hip) paired with straight-leg pants or jeans. That’s one of my “winning combinations” that I continue to wear frequently (although I also like to wear boot-cut pants on occasion).

Bad Shoes

I’m amazed at the number of bad shoes that I bought during the 2012 to 2014 time period! This was at the height of my resale shopping obsession, plus I was also very much trying to adhere to the “rules” espoused by Stacy London and Clinton Kelly on “What Not to Wear.” They often advocated wedges and heels, so I was trying to be a good student (which is also why I purchased so many blazers, blouses, and skirts during that same time period and a few years earlier). I cringe when I look at the shoes shown below, and I wonder how I could have worn any of them.

purged items: bad shoes

I realize that styles evolve and change, as do our sartorial preferences, but I question whether I ever truly liked the above shoes. Did I buy them all because they were “a good deal,” or was I trying to look the part of the sophisticated, stylish woman “What Not to Wear” was attempting to create? It was probably a “perfect storm” of the two (in its imperfection), but those are some ugly shoes!

The black suede pumps and the blue sandals aren’t that bad, but I wouldn’t wear any of the others today. Most are too high for me, and many of them are also either too formal or too “clunky.” I’m now okay with owning a smaller number of shoes (will do an update on this topic soon) and wearing a few pairs on repeat. I like shoes that are more minimal and classic in design than what’s shown here.

Too Formal and Conservative

I’ve written a lot over the years about how I lost my way with my style and somehow ended up with a more formal look than what I ultimately wanted. This was in large part due to the “What Not to Wear” influence that I mentioned in the last section. Since I saw Stacy and Clinton putting a lot of women in blazers, skirts, and heels, I thought that was what I needed to wear, too. However, I live a casual lifestyle in Southern California, so a lot of the outfits on the show weren’t appropriate for me.

I purchased a lot of my too-formal attire at consignment stores. I was experimenting with new styles, so it made sense to spend less money on them. Here are some of the formal and conservative pieces that I purchased 8-13 years ago that didn’t serve me well:

purged items: too formal

As you can see, there are a lot of garments there that would have been appropriate for working in a bank or a law office, but I wore these pieces for my everyday life! The skirts were too flared and the blazers were too corporate. The tops included too many ruffles or embellishments. I liked some of these pieces (I would still wear a sequined top now if I had an occasion for it), but they just weren’t right for the way I lived my life. Sadly, most of the items above were only worn a few times, if that, before being passed on.

Too Boho

Then there’s the flip side of the equation, those items that skewed too “bohemian” for my personal style aesthetic. Back in my twenties, I embraced the “boho-chic” style, so perhaps there was some nostalgia involved in purchasing the items shown below, but they didn’t work for me in my mid-to-late forties.

purged items: too boho

I don’t know what I was thinking in buying many of the above items! The bulk of them were found at secondhand stores, so maybe I got caught up in the “treasure hunt” aspect of that type of shopping. I probably liked elements of each piece, but there was just too much going on for me to truly feel comfortable wearing these items. I don’t think I wore most of them more than one or two times.

Two exceptions were the green-and-black-striped cardigan and the navy embroidered maxi-dress, both of which I actively wore for a few years. Ultimately, however, the appeal of the boho aesthetic completely vanished, such that I started to actively avoid it when shopping. As time went on, I no longer loved the drapey nature of the cardigan and the embroidery and tiered-bottom of the dress. Give me a straight-hemmed, non-fussy cardigan and a simple, streamlined dress and I’ll be happy.

Conclusion – and Your Thoughts?

As you can see, I made a lot of shopping mistakes back in the 2010’s, especially when it came to resale purchases. I bought many pieces that didn’t stand the test of time and often didn’t even hang around in my closet for more than a few months. It’s now abundantly clear to me why the items featured in today’s post didn’t work out, especially when they’re contrasted with the “oldies but goodies” that I covered in my last blog series (which I recapped in this summary).

I’m glad that I’ve taken the time to explore and define my personal style (which is characterized well in this 2020 post), as I now make far fewer mistakes and am happy with the majority of my outfits. Of course, the styles out in the world continue to evolve, as will our personal preferences, but I’m no longer “all over the map” throwing darts at various styles to see what might stick. I’m satisfied with enjoying certain styles on others while knowing that (and why) they won’t work for me. I still make some mistakes, as I’m only human after all, but it’s now – thankfully – much more the exception than the rule.

I hope you enjoyed this little walk down (cringeworthy) memory lane. Now, I’d love to hear from you. Here are a few questions to help you formulate your thoughts:

  • What style mistakes have you made over the years?
  • What types of items did you buy and rarely or never wear?
  • What lessons have you learned from your closet castoffs?
  • How has your personal style aesthetic changed from five or more years ago?

I welcome your shares in response to the questions above or in general. I look forward to reading what you have to say, whether it be educational, vulnerable, or just plain humorous. Thank you for reading and have a wonderful weekend! I’ll be back soon with a look at some of the items that I recently purged from my closet – and why.

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16 thoughts on “Items That Did NOT Stand the Test of Time – and Why

  1. Jenn says:

    Wow. I can see how knowing WHY past purchases didn’t work out can help us do better on future purchases. I usually delete purged items from my spreadsheet and Stylebook app. I think I’m going to move them to a “retired” section on one or both where I can note my thoughts on WHY I purged them.

    Thanks, Debbie

    1. Murphy says:

      Debbie, I can SO relate to falling under the spell of What Not To Wear! I also bought a lot of skirts plus twin sets and tall boots that hurt my feet. I will say that WNTW helped me to break my habit of wearing clothes that are two sizes too big, and I’m grateful for that. But a more subtle and casual style fits much better for my work and life in general.

      1. Debbie Roes says:

        WNTW was helpful for me in some regards, too, Murphy, so it wasn’t ALL bad. I think I just took some of their advice too literally and didn’t consider enough how it did or didn’t apply to my life. I wish they would have talked about that more because it is so important.

    2. Debbie Roes says:

      Good idea to create a “retired” section on your spreadsheet or Stylebook app, Jenn. I haven’t been tracking reasons for purging EVERYTHING lately (just when I do these types of posts), but it’s always helpful when I jot down my reasons. I use folders with item photos to track what comes in and out, but I think I’m going to include a text or Word file in the yearly “out” folder to track my reasons for purging. Sometimes that creates “lightbulb moments.”

  2. Sarah says:

    Your statement about when choosing what to wear in your closet having very little to do with its cost really resonates with me. I’ve repeated this twice to other people since I read it. Makes me think about my hesitation to buy something “perfect”, something I really could use and enjoy that costs a little more, versus the “pretty good” thrift or consignment item. You really have me thinking!

    1. Debbie Roes says:

      I’m so glad you found this post helpful and thought-provoking, Sarah! It’s so easy to get caught up in a “good deal” and settle in important areas. Of course, we CAN find great items at thrift and consignment stores or on sale, but it’s helpful to take a step back and consider other facets besides price before making a purchase.

    2. Cathy says:

      Thanks for taking the time to analyse the “why”. Its helping me to look more analytically at why I don’t wear some things in my wardrobe, and rethink the wisdom of my second hand purchases on eBay.

      1. Debbie Roes says:

        You’re welcome, Cathy! I’m so glad this post has gotten you to think more deeply about your eBay purchases. A little bit of analysis can usually help us to shop smarter.

  3. Terra Trevor says:

    Excellent closet clean out and insight gained!

    The joy of less and the space gained, and stress reduced now that you no longer have to carry the heavy mental load those clothes. I can strongly relate to this post. Much of what you have experienced I’ve gone through too. Too many resale fails for the same reasons you listed. Good post Debbie.

    1. Debbie Roes says:

      This closet clean-out occurred over a long period of time, Terra, but I thought it would be good to share it all in one post since it related to my previous series (just on the flip side). You’re so right that clothes can create a heavy mental load. I think people don’t consider that enough, especially when they have plenty of storage space. As for resale buys, I think I just wasn’t picky enough. Now I might be TOO picky, but I think that’s better than the other side of the spectrum. Glad you liked the post!

  4. Chris says:

    OMG! Debbie – such a good analysis and so helpful!

    I’m also a tall pear-shape in – 5′ 10″, so a lot of your likes and dislikes ring a bell for me. Currently, I want to especially thank you for your comments on grey tops.

    I make a lot of my own clothes and have a nice ash grey 100% cotton knit fabric in my stash that I’m planning to sew up next. I was trying to decide between making a pair of joggers or a relaxed tee. Reading this post reminded me that grey tops make me look ill. DUH! (How do I forget these things?) Anyway, I’ll be sewing up a nice pair of joggers or maybe cigarette pants.

    Thanks, Debbie! Love your blog…

    1. Debbie Roes says:

      I’m glad this post helped you make a decision about your fabric, Chris. The joggers or cigarette pants will hopefully serve you well! I have sometimes thought about learning to sew, especially since I’m hard to fit. As for color, I think it can be challenging when we like a color that doesn’t like us back. But wearing that color on our bottom half can be a good way to integrate it into our lives in a more flattering way. Happy sewing!

  5. RoseAg says:

    I got an old exercise DVD out recently and the instructor had on some of those bad capris that you mention. The routine was kind of a Beyonce/JayZ inspired dance and I think the bad capris were meant to emulate streetware at the time. The dance routine was fun and I like to do it, but the look isn’t for me!

    1. Debbie Roes says:

      Thanks for your comment, Rose. The “bad capris” were all the rage for a long time and many of us wore them. But who knows? We might look back on some of what we’re wearing NOW and cringe, too. I’m glad you liked the dance routine in the exercise DVD, as that’s the most important part of it! I guess their attempt at streetwear was a fail, but maybe you got a little chuckle from it 😉

  6. Low price point is probably the biggest source of my shopping mistakes because it is indeed easy to compromise and/or fantasize when shopping, and low prices/thrift stores can make me prioritize the excitement/thrill of the purchase (which is gone in no time) over the lasting value that an item will bring to my wardrobe….or even kind of forget that I need to consider something more than “I like it” before pulling the trigger on a purchase.

    I did get a good laugh at the corporate, boho, flared, orange/green, etc. items you rejected when compared to your current classic look with clean lines and jewel tones – not laughing at you, but at how some things can be so obvious in retrospect that were not at all clear at the time. Anyone who has struggled with a style journey can relate, and that set of not-working items paints such a clear picture. While it can be a bit daunting to see everything laid out like this, it also shows how far you’ve come, so congratulations! These are not purchasing mistakes that you will make now, so they have served their purpose along the way.

    One thing that really struck me was that you weren’t just flailing about randomly with your style – you were often following expert advice and rules of thumb that sometimes led you astray. This is a good reminder that no piece of advice works for everyone and that no expert can magically know what will work for your personal style, life style, climate, etc. I think your experience with deciding that grey is not a great color for you is such a good example of trusting ourselves over generic advice. But it can be hard to feel confident about whether something is working for us or not…and naturally the fashion industry does what it can to undermine the confidence we do have so that we will scramble to buy what the industry has decided is on trend this week. The fact that you are much more confident now shines through very clearly!

    1. Debbie Roes says:

      You’re so right that the thrill of a purchase is gone in no time, Sally. That’s especially true with sale and resale purchases. I really think it can be more about the excitement about finding “a deal” than the actual item itself.

      I didn’t know whether to laugh or be horrified when I was compiling this post. I knew that I had made a lot of missteps, but I don’t know what possessed me to buy some of those items! Thank you for acknowledging how far I’ve come. I think I wasn’t paying enough attention before to how I felt and was instead looking to “experts,” friends, salespeople, etc. The opinions of others can be valuable, but they should never supersede how we ourselves feel. Also, we can LOVE certain types of pieces on others but not on ourselves (that was responsible for at least some of my mistakes). I learned so much the hard way, but I’m glad that I eventually learned – and I hope that sharing my experience can help others not to have to take so long to learn!

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