It’s that time of year again. No, not spring cleaning, but the ever-necessary wardrobe decluttering that happens in order to make room for all the fabulous winter-wear you’ve been stocking up on. If you, like me, are a felon when it comes to clothes hoarding, the transitional closet decluttering can be really overwhelming. “When is it time to throw things out?” “What items can you sell?” “What if it comes back in style?” Or my personal favorite, “What if I don’t have money one day and need all these clothes I’ve saved?”. I am very guilty of living by the last one, which in theory isn’t all that bad of an idea, but in general causes me to hold onto things for way too long.


As I’ve been working from home and contemplating a possible apartment downsize next year, I’ve found myself extremely overwhelmed by the massive stockpile of clothing I’ve “saved up in case I run out of money for clothes”. It’s honestly gotten so bad that I’ve found it affecting my general mood. I’m constantly surrounded by an excess of clothing that I’ve amassed since around age 14 (Yes, that’s how bad I am about holding onto things), and it’s starting to clutter my mind. This week I sat down and forced myself to downsize my wardrobe. While doing this, I found 5 common questions I’m asking myself and the answers I’m learning along the way that are helping me finally breakup with old clothes.

1: Am I holding onto this item for sentimental value?

Remember that awesome dress you wore to that wedding, spent a decent amount on, and never wore again? Yeah, me too. Or how about that sweater you wore for senior photos ( or something along those lines) that is so outrageously out of style, but you can’t seem to let it go? Yeah, both of those are currently sealed up in vacuum seal bags under your bed never to see the light of day, right? They need to go. It’s pointless to hold onto items like these. Why? One, they will likely be gathering dust for eternity under your bed because if we’re honest we’ll never wear them again, and two, you potentially have photo in these pieces so why not hold onto pictures instead of the actual garment?

2: Does it still have the price tags on it because you thought it would be great, but totally ended up being totally unflattering?

Okay, this one is really hard for me. I used to be so bad about buying that really trendy piece that looks great on everyone on instagram, not trying it on, getting it home, thinking it’ll look cool with one specific outfit, but never wearing it because I just don’t feel confident in it. I don’t do this that often anymore, but had a lot of impulse purchases during my years of retail and styling. When I see an item that is either practically unworn, or genuinely never worn, I really struggle to let go of it. All I see are dollar signs wasted and I keep hoping that one day it’ll look good on me. Likelihood is, If I’m not going to grow 4 more inches over night, magically decide I want a hair color that doesn’t clash with it, lose 10 pounds, or shrink a shoe size, I’m never going to feel confident or comfortable in these items. This is when resale comes into play. If the item is in good condition and still relatively unwashed and unworn, I like to utilize either apps like Poshmark, Ebay (if it’s a brand name), or the plethora of recycled clothing and consignment stores.


3: Are you holding onto it hoping one day you’ll be the same size you were in high school?

I have probably held onto more clothing from my teens than any age since. I was really into suiting and expensive formal dresses during my late teens, and a lot of my pieces are still relevant to today’s trends. That being said, I had all of them tailored to my “No hips, No butt, No shoulders” teenage body. If I’m honest with myself, I know I’ll never fit into those again, and it’s really unhealthy to hold onto something hoping I will. We all do this, maybe not for items from our teens, but we are all guilty of having that “when I lose weight” item I’m pretty sure. It’s hard enough to have a strong sense of confidence in this digitally enhanced age we live in, why torment yourself by holding onto something that is a constant reminder that your body shape either isn’t what it used to be or is a work in progress? Love where you are, not where you’ve been! You’ve just gotta break up with them and move on, no matter how pretty and glittery they may be. They don’t fit. They won’t fit. They make you lose confidence. They need to go.

3: Did you buy it because your BFF, significant other, or someone else told you they liked it?

I’m not really a serial offender on this one, but I’ve definitely done it a few times. Back when Ben and I were dating, I was definitely guilty of buying outfits specifically because I knew he would like them, but they were a little out of my style comfort zone. Nothing wrong with trying out something new and taking style cues from someone else’s preference, but at the end of the day, your body is the one wearing it. If you don’t feel like you are rocking it, no amount of compliments from friends or family are going to make you feel stellar wearing it and most likely you know that deep down. If you’re holding onto it just because someone other than you liked it and it hasn’t been worn in at least 6 months, it’s a definite sign that it’s time to sell or donate.

4: Does the item make you unhappy?

Okay, this is a really weird one that may just be specific to me. Similar to items held onto for sentimental value, there are items I’ve held onto because they cost me a lot, but make me remember times I’m less than pleased to be reminded of. Unfortunately, this is the majority of my stock pile. When I worked retail as a stylist, a lot of the companies I worked for required I wear either specific trends in clothing or branded pieces only. Sadly, that meant that a large portion of my paycheck often went towards clothes that definitely weren’t my style, but were what I was required to wear. These weren’t the happiest of times for me, so a lot of these pieces hold negative sentimental value (if that’s even a thing), but I hate to sell or donate them because they cost me a small fortune at the time. When it comes to pieces like this, I’m finding how toxic it is to keep them around. Sure, I’ll never make back what I spent on them, but as long as they aren’t threadbare or horribly stained, they will be of more worth sold at a fraction of the price than they would sitting around making me unhappy.


5: Would you buy it now if you were out shopping?

Not gonna lie, this one I totally stole from the web while I was in a panic trying to get decide on how to get rid of my closet clutter. But honestly, this is one of the very best “questions for self” I’ve heard. It really did make the decision for me on a lot of items. Most likely if it’s been relegated to the back of the closet, rarely worn, or maybe never even made it out of packaging, you wouldn’t buy that item again if you saw it while you were out. And that’s a sure fire way to know you’ll never wear it again. 

Okay, now that we’ve gotten through some of the major reasons why you may be hoarding, let’s talk about when to sell and when to donate and when to just throw it away. As a general rule of thumb, if the item is overworn, stained, damaged, or an undergarment, THROW IT AWAY. If the item is formal, lightly worn/lightly washed, name brand, new with tags, free of stains, discoloration or damage, sell it. Usually I will try to sell items first at either a recycle type store (Buffalo exchange, Plato’s closet, Clothes Mentor etc.) or consignment before I attempt to sell it online. The only time I break from that is if the item is name brand or new with tags and I know I can sell it online faster and for more money than I would at any of those venues. Now, if consignment or recycle stores deny your item, and you’ve spent more than 3 months trying to sell it online, it’s time to accept the fact that it’s just not sellable and you need to donate it — that’s one of the hardest facts to face–. Donate your items if, they have been slightly altered, semi-well worn (No holes or major stains), are suiting items you weren’t able to sell (These can change someone’s life who is in need), trend items from fast fashion shops that have no resale value, or are just items that won’t sell even if they are name brand or new with tags. Better these items bless someone else, than sit and collect dust in your closet!


I hope you guys found this article helpful when it comes to breaking up with old clothes, and help you find a less cluttered and more mentally freeing lifestyle!