Hmm - bitterness is too strong a word. Slightly annoyed and disappointed I'll go with.

I'm trying really hard to avoid regrettable purchases by forcing myself to return things if they aren't exactly right. For online shopping, I mentally prepare myself to be ready to return the item before it even arrives. For local shopping, my rule is to never buy anything at first sight. If it's worth driving back for later in the week, then it's probably worth keeping!

This means I try to avoid clearance racks where everything is final sale, and I mostly shop places that offer free return shipping or where I can return the item in person. I also find I'm thrifting less than I used to, because thrifting is just such an easy way for me to make bad impulse purchases. And I'm often more attached to thrift store finds because they're "one of a kind."

I leave tags on new purchases for at least a few days, try items around the house with different outfits (do I have shoes that work with this? can I layer under/over it? is it worth tailoring? etc). I usually make "final cut" decisions on the weekends, when I have the time to print out return slips and pack things up right away, so rejects can go right into the mail on Monday before I have a chance to second-guess.

I also find it really enjoyable to sell things online, so when I do make a bad purchase (usually impulsive clearance sale stuff) that isn't returnable, I'll take photos and get it up on eBay or Tradesy right away, while it's still NWT. I actually have a little section of my closet now devoted to potential eBay items. For the most part I manage to break even and sometimes even make a few bucks. But I'm a diehard "deals" shopper, and I almost always check around to see if I can find the same piece secondhand before I buy new.

Umm....I rarely ever feel any bitterness towards wardrobe items. Like Deborah, I'm happy to pass on things when they don't work for me.

However, I've been a bit too *purge-happy* this year. I purged items without a second thought, and there are a couple of shirts I think I passed on too soon. Yet, no regrets.

In the future, if I don't love something, I'm going to shift it into storage area for a little while (holding zone) before I completely get rid of it. This, however, will NOT happen for shoes or handbags. Once I realise there is something wrong - bad fit, not comfortable enough, access too tricky inside some bags - out they go.

I had two Newburys and I sold one of them (in gray) last March. I kept the black ones. I think with higher shaft booties coming back, they work. Also they were all over the October Nordiies catalog, in lighter brown granted.

I also find them quite comfortable for a high heeled bootie.

But if you are not wearing them -- consign or eBay! You will surely fetch a better price and sell more quickly than if you wait until the final stages of your relationship. I try to let go of pieces earlier, rather than later. Yes I have regrets every once in a while but I have so much stuff, does it really matter.

If I wait too long, the item almost always goes into the donation bag rather than the eBay bag.

I'm with Adelfa. I tend to hang on longer rather than jettison too soon (hmm, there are parallels with my relationship history there, prior to my husband of course!).

I'm due for another closet edit. A couple of weeks ago, I pulled out some winter things from storage and tucked some summer stuff away and thought, wow, I have some room in my closet now! Is that all the sweaters I have? I can shop for more! ;-P And then this weekend, when it got cold, I realized I had a cashmere hoodie (or three) to pull out and wear around the house, and that those were still in out-of-season storage. Oops, there was a whole pile of sweaters in storage I had forgotten about (not to mention some holding zone things that I'm avoiding looking at). Some of them I was not excited to see -- rather, I felt guilty that I no longer feel excited to wear them. I think that's a sign.

Traditionally, I held on to things as long as possible. This would involve a lot of trying on, finding them not quite right, but keeping because I felt I should have this type of item. Or I might be able to make it work. Or especially because of the price and letting it go feels like a waste. But I've come to realize that none of these factors made me love reaching for a particular item and if I don't feel fab in it, it's never going to become a workhorse. So I've been trying to get better about letting things go.

For me, the guilt of letting things go is short-lived but the guilt associated with holding on to a bad purchase is never-ending...

Thank goodness for DH I treat him differently than my clothing. I turn on my clothing in an instant and out it goes. I've hung on to him through all sorts of indignities.

So I made myself wear the Newburys yesterday (a state holiday but school in session, so lunch date and errands with DH) as a sort of "it's not you, it's me" moment. Nothing new transpired - they are not comfortable but not UN-comfortable for short walking stints at a slow, stately clip (not my usual pace!).

The big shocker was that DH loved them - he never notices boots (except to roll his eyes) but he made a point to say how much he liked the look. OF COURSE. I was wearing them with grey skinnies and a forest green sweater. And I felt like I looked good.

Apparently I'm still waffling....

Firstly, I love those Newbury boots. But way beyond my poor NZD budget. Stretch them to giant hoof size and throw them down to me!!

If it is sentimental I hang on, but mostly I know when it is time to edit. I don't change size all that much (this has good and bad aspects because I am no sylph) but most clothes fit me for a long time.

My resentment lies over my clumsy slobby personality- I ruin clothes. My very favourite designer tee (I only have two designer tees) has a bleach orange spot among the black gorgeousness. And my blush sweater that has been featured a million ways on here now has a stain on the front - it is not huge but it ruins the creamy soft nature of it. I get very cross with myself for being such an oaf.

@alaskagirl, that happens all the time to me w/ DH! He manages to only compliment me on things that I've decided to get rid of, or that are about to fall apart!

I still think you should keep them. I rarely wear mine but am really happy they're there when they are just the thing.

I love your comment about DH rolling his eyes about your usual boot. My DSO is very fashion supportive but my DM (mother) rolls her eyes at EVERYTHING that is not a Lands End twinset, straight Eileen Fisher stretch pants or Ecco shoes. 90% of my closet.

The comments on here are hilarious! What a pleasure to read you all. Alaskagirl, you pose a very legitimate question. There is so much emotion tied to some items... and then we feel betrayed when they don't keep their promises. It's like they let us down. They operated under false pretenses. Underneath it, hides our true sensitivity towards ourselves, our place, our bodies, our lives. Also hides our insecurities.

I am the queen of mistakes.

Sometimes, finding out something was an error of judgement becomes crystal clear very quickly, in fact, sometimes so quickly the tag is still on it. But too often a "mistake" becomes evident only a year later in the form of a closet orphan. A love-at-first-sight item has a minor downside to it. It turns out the downside in question was major, in the end. Major enough that it prevented me from wearing the item.

Or sometimes it's not a downside, but simply a fit or proportion issue. The pretty thing simply does not flatter my body type, period. Meanwhile, I happily innocently go on with life, convinced the item is crucial to my wardrobe. Until one day... boom. I get mad at myself for not recognizing it sooner, despite so much practice.

And then there is the case of the mistake born out of a mistake. It's like they can reproduce, you know. And infest our closets! Let me explain. You acquire a piece, say a top, which fits a closet hole: it's white, it's short sleeves, it's more chic than a cotton tee. Gee, it even has this trendy uneven hem which looks so in. (Very often this scenario happens when you acquire the said top at a sale). Then you find you are not reaching for it as much as you hoped for. "Ah well", you say,"must be because I have another closet hole in the bottom department. I just don't have the right pants to wear this with". And so a new quest is born. Little do you know that you have just stepped into an endless, fruitless labyrinth that can only possibly lead to... another mistake. Which you end up this time paying full price for. Then, you still do not wear the pieces, except the bottom maybe a couple of times separately, and purely to calm your conscience. Then a year later, you finally wake up from your dream and enter full lucidity mode. The tee was not right from the start, period. It was that hem, in fact, that was difficult to work around. It kind of floated over your waist, cutting you just at the wrong place, making you feel like a potato. If you had seen it from the beginning, you would have avoided buying the pants on top of it, and you would have put your energies into looking for the right white short sleeves top. That was an example of a mistake generating orphans. Now what about the pants you paid full price for but almost never wear? Should you get mad at them too? It's not their fault, they never asked for anything... yet, here they are taking valuable space in your closet, with the memory of their high price attached to them. Sigh.

Wow, Krish - could not have been more on point there. Nodding my head the whole time I was reading!

I think I have the same mustard color from BR that I don't wear but the sloan pants, Una! I can't bring myself it get rid of them...I keep thinking I will wear them with tall boots this fall..which I'm really going to try. Every time I look at them hanging in my closet I feel guilty and am reminded I dont like to wear that much color. But I love the color:(

I am thoroughly enjoying this thread but keep getting distracted by love life parallels. Hmm, trying to focus on clothes, for me it is more like when love turns to "what was I thinking". Parallel to my pre-DH social life implied.

Nope, I love forever, even when it is unrequited. Never bitter even when I am ready to move on. That's the honest emotional answer.

If you want to sell the Newburys let me know! I have been hearting them for years but always held off due to the high heel. I can use them even less now that I am a SAHM, but heck. I love those beauties. So sweet that your SH noticed. Maybe keep them for his sake and date/together time.

I bought these Steve Madden Nonstp sandals back in April. I LOVE the look of them. I shouldn't have ignored the description (heel height 3.25). They are just too tall for me. I haven't gotten rid of them yet, but I've only worn them a handful of times instead of what I expected.

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