Do you have trouble parting with your clothes (even when it’s time)?

This week, Heidi asks how to know when it’s time to say to goodbye to the pieces in her closet–especially the more expensive items.

Here are 10 Questions to Ask Yourself When Editing Your Closet (listen to the episode for more info!)

  • Do I like to wear this?
  • Do I wear this anymore?
  • Do I feel good in this?
  • Is this in style? (or my style?)
  • Does this look shabby?
  • Can this be repaired/altered/updated?
  • Would it require more work/money than I’m willing to invest?
  • Am I hanging on to this hoping something will be different?
  • Am I hanging on to this hoping I’ll be different?
  • Am I keeping this because I don’t want to lose money?

Plus, Heidi wants to know when something is too worn to donate, and I borrow advice from a past guest to make the decision easier. Listen to Dana Marlowe’s advice on what to donateFind ways to responsibly recycle clothing.

I’d love to know why YOU have trouble getting rid of clothes–share with us on Facebook or Instagram!

Links & Resources from the Episode:

Take 15% off of your Living Wonder Purchase with code STYLE15

*This post may contain affiliate links, which means that I may receive, at no cost to you, a small commission from purchases made through links we provide. 

Listen to the Episode Now:

Stitcher    Spotify    Apple Podcasts

Read the full episode transcript below: 

Today’s episode of Office Hours is sponsored by Living Wonder. Living Wonder premium supplements help you look and feel great–and that’s what we’re all about here at Everyday Style.. I use Living Wonder’s Collagen Boost Plus everyday to help my skin look younger, and I love it–I hope you will too. 

Everyday Style School listeners can take 15% off their purchase by going to and using code STYLE15. As always you can visit our show notes for the link.

Welcome back to Office Hours–the weekly show of the Everyday Style School podcast, where we answer just one question, submitted by you lovely ladies, to help make style easier, and getting dressed more fun. 

This week’s question comes from Heidi who wrote:

I love your show! Your episode on caring for your wardrobe leads me to the question, “How do you know when it is time to retire items in your wardrobe, particularly more expensive items like shoes?” Also, aside from obvious rips and stains, when are items too worn to donate?

Great question Heidi!  

I think my advice would be the same for expensive and non-expensive items alike. That question makes me worry that you’re equating price and value–and as everyone should know by now, they’re not the same thing. Price is the money you paid for it, value is it’s usefulness to you right now. They have very little to do with each other.  So, regardless of how much you spent on something, here are 10 questions to ask yourself to determine if it’s time to say goodbye. I’m going to go through these quickly, but head to the shownotes on our website for the list. 

1- Do I like this anymore?

This the most important question to ask yourself. The bottom line is, if you don’t like it, you’re not going to wear it. We change over time, and we have to allow our style to change too. If you’re hanging on to something you used to like, but now don’t, give yourself permission to let go of it. 

2- Do I wear this anymore?

This is kind of the flipside of question #1. Often, we don’t stop liking something…in theory…but in terms of practical application, it’s just not right anymore. If you used to go out all the time, and now you spend your Saturday nights at home with kids, your collection of cleavage baring going out tops may not be super useful anymore. You can still like them, but if realistically, you’re never going to wear them, keep your favorite one, and let the rest go. 

3- Do I feel good in this?- I talked about this a few weeks ago in my philosophy segment, but things that you don’t feel good in either physically, or psychologically are never going to become staples of your wardrobe. I know every woman has an uncomfortable bra–you put it on, it feels terrible, you take it off–and what do we do with it? We put it right back in the drawer. Why? It’s never going to feel better. THe same with clothes that we psychologically feel bad in. I had a dusty purple cardigan for years that I bought in an emergency panic shopping session. Paid way too much for it, and hated the way I looked in it. The color was drab and washed me out, I felt frumpy everytime I put it on. Finally, I donated it. Life is too short to wear clothes that don’t make you feel good. 

4- Is this in style? This one has some subjectivity to it. If you don’t care if something looks current, and you just want to wear what you like, go for it. But, if you’re someone who does want to look current, ask yourself if the item looks like the things people are currently wearing, or what’s being sold in stores. Hop online and look at the stores that represent the astechic you want people to see…like, Jcrew for example. If they don’t have anything that looks like what you’ve got, chances are, the item is no longer in style for that aesthetic. You might hop over to eddie bauer and find a perfect match, and if Eddie bauer is your style, great. If not, well, you can decide to keep it, or let it go

5-Does this look shabby? This is a question you should be asking yourself frequently. I’ve talked about the quality issues we have today, and how fabrics just don’t hold up, but nothing will make you look frumpier faster than shabby looking clothes. From pilled knits, to scuffed shoes, if the item looks worn out, it’s time to fix it or pitch it. Which brings me to

6- Can this be repaired/altered? Some shabby or dated items just need a little refresh. A date with a fabric shaver, a dunk in some fabric dye, or a trip to the cobbler for a resole. Some items are beyond repair, though. Belly holes can’t be fixed. Stretched out shoes can’t be brought back to life.  If you’re not sure, google it, and find out, or call a professional. If it can’t be fixed, it needs to go.

7- Would it require more work/money than I’m willing to invest? Even if your items CAN be repaired, refreshed, or altered, be honest with yourself and ask how much you’re willing to invest to make that happen. Yes, faded black tees can be redyed, but are you really going to invest the time? Yes, most shoes can be resoled, but do you love them enough to invest the money? This is one of those times when good intentions aren’t enough. If you realistically aren’t going to invest the time and or money, just let the item go.

8- Am I hanging on to this hoping something about it will be different? If you find yourself saying things like “I would wear this ‘if” dot dot dot” stop yourself right there and put it in the donation pile. For example, I would wear this dress if the neckline was a little more open. I would wear this shirt if it was a little longer. I would wear this if the color wasn’t so draining. Like I’ve said before, there is no wardrobe fairy coming to your house in the middle of the night to make things magically work for you. That item is not going to change. The shoes will always be uncomfortable, the sweater will always be scratchy. Make your decision based on reality, not your wishful thinking. Speaking of which…

9- Am I hanging on to this hoping I will be different? If you feel like you’d need a different body, different coloring, different life, different lifestyle, different job, or different style to wear the item in question, let it go. Don’t wait for someday. Don’t think a pair of $29 clearance dress is going to inspire a life change. It won’t. Make your wardrobe meet you where you are, instead of the other way around. and

lastly, 10- Am I keeping this because I don’t want to lose money? This goes back to the original concern about getting rid of expensive things being different than getting rid of inexpensive things. I feel like a lot of women need to write this next part down. The money is gone, and keeping things you don’t wear isn’t going to bring it back. You can’t recoup your investment simply by hanging on to things. Ask yourself, if I don’t look at these shoes, or this dress for the next six months, and then I get rid of it, will I feel better about the money? What’s going to change? Spoiler alert, nothing. If you spent a lot of money on something, and wore it to death, get rid of it, and give yourself a pat on the back…you got real value out of your investment. If you spent a lot of money, and you didn’t get value out of it, there’s nothing you can do. Let it go, and vow to do better. That’s all there is. 

Finally, Heidi asked when something is too worn to donate. I love what Dana Marlowe from I support the girls had to say when we had her on the show this Spring. If you wouldn’t give it to your sister or your friend, it’s probably not donateable. Keep in mind, like I shared on our episode about creating a wardrobe that’s kind to the planet, there are way more pre-owned clothes out there than there are people who need or want your pre-owned clothes. Chances are, if you donate it to a charity that will eventually resell it, unless it is in pristine condition, it’s going to end up in a landfill or shipped to another country. You’re much better off disposing of it yourself in a responsible way. Take a listen to that episode, or revisit those shownotes for textile recycling ideas.  

Heidi, and everyone else, I hope this episode gave you a little more clarity on when it’s time to let go of your things. The last thought I want to leave you with is this: A great wardrobe is just as much about what you take out, as what you put in. Be ruthless in your editing for a truly great wardrobe.

Head to your favorite social media spot to continue the conversation. You can find us  on facebook and instagram at Everyday Style with jen, or head to the shownotes for the link.

If you’ve got a question you’d like me to cover in Office Hours, email it to

Visit our website for links and resources from today’s episode. You can find them at Click on podcast and find the episode you’re looking for. 

Thank you to Living wonder for sponsoring the show, head to to take 15% off of your purchase with code Style15

That’s all for today–see you next week! Until then, stay stylish!

Are you on the list? Sign up now to get a Style Tip and Product Pick every week, delivered right to your inbox!

Similar Posts