Do You Really Love It? 3 Ways to Determine It’s Time to Let Your Clothes Go

Posted On Monday, February 15th, 2016
Filed Under: Style Guide

Closet Clean Out: 3 Ways to Determine Whether to Keep or Toss Your Clothes

“Do you love it? Really love it?” 

This weekend I helped a friend clean out her closet and that’s the question I repeatedly asked anytime she tried to add a garment to the keep pile. And her response was either “no” or “it’s okay, I like it.” Having a closet full off “okay” pieces is the quickest way to end up with an excessive amount of mediocre clothes and accessories that just take up space and don’t represent your personal style. But I know it can be hard to decide what you should keep or toss.

If you’ve ever struggled with deciding how to determine you love, like really love a garment or accessory, here are some tips.

How Do You Look?
This sounds like a no-brainer, but hear me out. Do you look amazing when you wear the piece of clothing? Does it flatter and highlight your favorite body part{s}? If so, keep it. It’s totally acceptable to be vain for a second here and look at yourself in the mirror and think, “yup, I look great!” If you can say that, it’s a keeper.

On the other hand, be real with yourself and acknowledge when you might not look your best. For example: if you have to wear several pairs of Spanx to fit into a dress, it’s not the best fit. Or if you’ve found a great fitting piece but the color washes you out, let it go.

Closet Clean Out: 3 Ways to Determine Whether to Keep or Toss Your Clothes

How Do You Feel?
It’s totally normal to have an emotional attachment to clothing. I’m pretty sure everyone does. It took me forever to get rid of an ugly grey dress I had hanging in my closet. Why did I keep it? It was the dress I wore when I got laid off from my job at a fashion magazine and I looked at that day as super liberating and what ultimately led me to create Looking Fly on a Dime®. Great story, right? But the dress just wasn’t my style and the color was horrible on me. So I finally got rid of it. With or without the dress, I still remember that day vividly, so the memory hasn’t changed.

However, sometimes feelings can play a major role in deciding to keep an item.

Do you feel comfortable, confident and are you just feeling yourself when you wear that article of clothing? Like, your mood instantly picks up when you wear it. Some clothes just make you feel amazing. These are the ones that have a place in your closet and will get tons of wear.

Now, I’m not talking about your ratty, stained sweatpants that you feel comfortable in, those don’t count. But this is more about the clothes you wear to work, the weekend and when you’re having a fun night.

These 3 questions make it easy to determine what to toss vs. keep in your closet. Click To Tweet
How Do Other People Think You Look?
Now, I’m not saying your validation should come from outside sources, but sometimes others can see things we can’t. You might think you don’t look good in bright colors, but if everyone seems to compliment you on that bright cardigan you wore one day, you might want to consider that you actually do look great in bright hues.

For example, I had a jacket I thrifted a few years ago and I finally started to wear it. When I did, it was a showstopper. At least three or four people that day commented on how they loved my pretty jacket. That jacket has since become a staple in my closet and I’ve found multiple ways to style it.

Closet Clean Out: 3 Ways to Determine Whether to Keep or Toss Your Clothes

That’s not to say you should seek out validation {don’t fish for compliments!}, but if you’re noticing a pattern of unsolicited compliments in regards to a item of clothing you wear, others might be on to something. Take notice of this.

When you decide to toss clothes you don’t really, truly love, don’t get freaked out if your closet is looking a little light. That just means you’re making space for the things you really love and you’re one step closer to defining your personal style. Remember when I cleaned out my closet and ended up donating a fourth of my wardrobe? It was the best thing ever.

Do you have a closet of items you love or random pieces? How do you go about cleaning out your closet? 

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8 thoughts on “Do You Really Love It? 3 Ways to Determine It’s Time to Let Your Clothes Go

  1. I definitely think about these things when cleaning out my closet! I read a tip somewhere about letting yourself keep a few things for sentimental reasons, but just storing them separately so they’re not mixed in with your regular clothes.

    A big one for me too is to not keep things based on guilt. It’s so easy to say “But I paid a lot for it” or “I just bought that last month!” But neither of those is a good reason to keep a piece that isn’t working for you!

    • Ah, that’s a great tip about keeping things out of guilt. I realized I’ve done that with a few things, especially if it was something someone bought me. That feeling of obligation can make you feel inclined to keep the item!

  2. I had a really hard time determining if something looked good on me. Was I loving it for the wrong reasons? Keeping it for old time sake? So I set up my camera on a tripod and took my picture wearing items I was unsure of and some that I was positive looked great on me. Well it’s true what they say, a picture is worth a thousand words (and some of those words can’t be repeated here). Ha! Looking at yourself in a picture is a completely different “view” than the one in the mirror. It really helps you see yourself, your shape, your good and maybe not so great parts and it will definitely help you define your style. Love your blog! Thank you! Liz W.

    • Thanks for the comment, Liz!
      And yes, pictures will ALWAYS tell you the truth, so taking pics is a really great tip. Also, moving around in a garment (sitting, walking, etc.) can determine whether it’s a keeper and how it really fits your body.

  3. Thank you for this article. I cleaned out my closet some time ago but I know need to go back and get rid of a few more items. I’m feeling nervous because it’s already resembling the light” look you mentioned. Ughhhhh! I know it’s for my own good, so I’ll push forward. I’ve used the help of TRUSTED friends to clear out items. There also have been times when I would get dressed, go out and later end up in a funky mood. Not sure why at first only to figure out that I was miserable because the shirt or pants I had on made me look frumpy. I now immediately put those items in a bag instead of putting them back in my closet. If you haven’t worn something in a long time. Force yourself to wear it. You’ll know whether or not you want to keep it. After you’ve had it on for awhile. The last piece of advice someone gave me was to ask yourself would You buy the particular item today. If the answer is no, it has to go.

    • Ah, great feedback Liz!

      And you’re so right about the “would I buy it today” advice. That’s a great way to tell if you really want or need the piece.

  4. I also read somewhere that if a piece of clothing has a bad memory attached to it you should probably get rid of it. I had a beautiful outfit that I bought specifically for my mother’s funeral. That’s the only time I ever wore it. It hung in my closet for about 2 years and I finally donated it. I couldn’t wear it again.

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