I'm Forcing Myself To Wear Beloved Old Clothes I Can't Bear To Donate

I rarely wear these clothes anymore, but it’s like they have feelings and if I break up with them, they will be deeply hurt.
Publish date:
July 18, 2014
old clothes, sentimental value, throwing away old clothes

I clean out my closet at least twice a year, usually when I’m switching my warm-weather clothes out for my cold-weather clothes and vice versa. Ever since I really got serious about organization (so, like, pretty recently), I've decided that if I haven’t worn something in the past year, it’s gotta go.

This year, I’ve really tried to minimize my closet. I’ve given away/sold/donated/passed down more clothes in the past six months than I have in probably the last five years. But I have pieces in my closet that, no matter how hard I try, I just cannot get rid of them. I still have clothes from middle school.

I don’t think there’s anything wrong with holding on to something if you’re still using it. My problem is I rarely wear these clothes anymore. Honestly, I couldn’t tell you the last time I wore any of these items. But it’s like these clothes have feelings and if I break up with them, they will be deeply hurt. I try to remind myself that clothes are inanimate objects and even if I get rid of them, they will probably find a new home with a new mom and can still live a happy life; but on any given Saturday afternoon, when I’m in the zone, jammin’ out to something hardcore like Paul Simon, throwing clothes into sell/donate/throw-away piles, I reach these pieces and almost -- ALMOST -- throw them out.

Almost doesn’t cut it, and I always end up hanging these pieces back in my closet (carefully, so they know they are still loved) whispering empty promises softly to them (“I will wear you soon”). What is it that makes me hold on to these pieces?!

The Out-Of-Character Denim Mini Skirt

I bought this skirt about six years ago. I’ve never been one for tight skirts, and I’ve never, ever been one for denim skirts. I think I bought this on one of those shopping trips where I was trying to force myself to try stuff I would never wear, like getting out of my comfort zone or whatever. I don’t know about you, but any time I buy something different or try something new, it usually just sits in my closet under all the same, comforting stuff I do wear.

And that’s where this skirt has been. For years, and years. So, I guess guilt is the reason I’ve held on to this little baby. I’ve worn it maybe once or twice since I got it, but when it comes time to throw it out, I feel guilty for not wearing it more and tell myself I’ll wear it a couple of times and then throw it out. Unfortunately those "couple of times" never come and I obviously still have the skirt.

SO... I’ve paired it with a simple striped sleeveless tee and some peep-toe flats for a casual cool look. I like skirts with T-shirts and didn’t want anything too fancy up top since the skirt is already so tight.

The Skirt-Shirt Thingy

I bought this item at a consignment store when I was 16. It’s Free People, and in my teens, that was my favorite brand ever. I knew I could never afford this full-price, so when I found it for 10 bucks, I thought I had made it big.

The thing about this piece, though, is that I was never sure if it was meant to be worn as a skirt or shirt. Since I bought it second-hand, there was no tag indicating exactly what it was, and I ended up wearing it both ways. I go to the beach maybe once a year in the summer and I’ve really only kept this skirt-shirt because I feel like it’s the perfect easy-saltwater-sandy-beachwear piece. Basically, I’ve held on to this tie-dye beach dream for years only to pack it up once a year and maybe or maybe not wear it out on vacation.

In another attempt to truly wear my much-loved skirty shirt, I’ve styled it two different ways. But because I’m not that comfortable in strapless pieces (unless I especially want to look naked in close-up pics), I kinda dig it better as a skirt.

The Questionably Colored Tunic

My older sister is probably laughing as she reads this. We’ve been through a lot together, and we’ve been through a lot with this tunic. I got it in eighth grade, and I loved it from the moment I saw it on the mannequin. I remember searching the store for it, and finally, after an hour of looking, gave up and gathered the courage to ask a sales associate to get it off said mannequin for me. (This was a huge deal because I was soooo shy when I was younger and avoided verbal communication with anyone I didn’t know at all costs.)

What I loved about this top was its vintagey look and feel. I adore the color and quilted detail on the top. Sad thing is, I really don’t think it’s a very flattering color on me. My older sister, Anna, and I have passed this shirt back and forth for the last eight years or so. Sweet, sweet memories have been made in this top, and at the time, it really was my favorite piece of clothing. Maybe that’s why I’m so attached to it.

I used to get away with wearing this as a dress, but I have grown a couple of inches since then and numerous wash/dry cycles have caused the garment to shrink a good bit, so I paired it here with skinny jeans, and belted it to give myself some shape. I feel like this is really the only way I would be able to wear it nowadays.

The Off-White Almost-Crop Top Like All My Other Ones

I went through a stage about seven years ago when I seriously had at least 15 off-white/white tops and I could not stop buying them. This was one of those purchases I tried to talk my self out of: YOU HAVE 15 TOPS JUST LIKE THIS KW. But no amount of yelling quietly in my head could stop me. I’m pretty sure it was on sale, too, and I also have a problem with buying clothes (or anything, really) just because its’ on sale, so…

I’ve tried to get rid of this top plenty of times because it’s slightly ill fitting on me -- a little too tight in the chest and arm areas, so much so that I have to keep my arms a certain way at all times so it doesn’t pull funny. I keep telling myself that I just haven’t found the right way to wear it yet.

Maybe this time is the charm? I’ve paired it here with some high-waisted floral jean shorts. I love the idea of lace and denim together, and the floral print adds a little something extra. 

So, should I keep these sentimental pieces or finally cut the ties that bind (cue Springsteen) and get rid of them? How would you wear them? Do y’all have pieces in your closet you’ve had for-e-ver and just can’t part with? Let me see!