If the Jeans Fit: When and How to Get Rid of Clothes

How do you know it’s time to get rid of clothes? There’s always a “what if,” whether it’s a piece that served you well in the past, or something that still has tags a year after you bought it.

Cleaning out my closet is emotional for me. Who knew clothes could be so nostalgic? Plus it sometimes makes me yearn for my pre-baby days when I had the BEST boobs and hips and didn’t look bloated from my feet to my face. My body has never been the same after having two kids in my 30’s- And that’s OK!

But it doesn’t mean I don’t miss my old clothes…

The case for holding on

I’ll hold on to a few old dresses I wore in the 90s and early 2000’s because eventually they’ll come back in style, right? Every 90s teen and young adult remembers how popular Betsey Johnson dresses were, so of course, I saved some of her dresses in an old suitcase to pass down to my kids or nieces someday, along with my fave Express dress from 2004.

I also saved clothes from designer brands that just aren’t around anymore, or as “trendy,” because I love that they’re considered ‘vintage.’ (For example, I have a pair of Todd Oldham jeans I wore to death in college that are so nostalgic to me, and remind me of good times. I just can’t toss them. I’ll never fit into them again, but I still love them. Into the storage suitcase they go.)

I lived in Manhattan in my early 20s, and loved vintage clothing shops back in the day, so I’ll never toss old vintage jackets I got on Bleecker Street, or this grey dress I wore on dates and Girls Nights back when NYC was feeling vibrant again in a post-9/11 world.

They no longer fit, or no longer make you happy

I asked two fellow mamas how they organize and toss their clothes

“I have two methods for the best time to part ways with clothes,” says celebrity wardrobe stylist, Pilar Scratch. “When the clothes no longer fit and no longer make you happy. If I look at a garment and I’m not excited; I get rid of it.”

Adds Pilar: “As a mother, my weight has gone up and down since giving birth to my son. Once I reached a size four I knew it was time to get rid of my 8+ clothing. I typically donate my clothes to the local Salvation Army or my favorite thrift store. If the clothes aren’t wearable I will toss them out.”

Pilar does have a favorite shirt that she has “great memories in — I will absolutely keep the garment.”

Getting rid of clothes can feel like the end of an era

My last full-time office job was 10 years ago, and I wore formal pants and polyester tops every day for 8 years…all those Ann Taylor and Banana Republic clothes, although nice at the time, never really felt like “me” (think black cigarette pants and pleated, floral tops) and so I donated them years ago to Housing Works in Tribeca, NYC. Because my career changed from in-office to in-house, so did my attire.

Nicole Murphy, veteran model and founder of beauty and wellness brand yFOY, talks about her old maternity clothes. “Honestly, after being pregnant five times I couldn’t wait to get rid of my maternity clothes. I did not want to look at them anymore, so I donated them.”

I can relate to this, but I kept a few cotton maternity tops because they’re comfortable to sleep and lounge around in. I donated or tossed everything else.

Using the beloved jeans as “inspiration”

I’ve definitely done this, and Nicole admits she has too. “Sometimes I’ll pick up those jeans and say, ‘Ohmigod, these are so cute! If only I can still get back in them — I may be able to fit these jeans again.’ Now recently I came to the realization that I’m older and my body is just not the same. I have to work extra hard to lose weight and I have to realize there’s no way I’m getting back into those jeans anymore and I need to let them go because my body is different.”

Nicole points out that letting go of your old jeans can also be an excuse to buy some new ones.

We love a silver lining.

I also personally toss old t-shirts and tank tops, especially if they’re faded, stretched out, and the cotton is thin from so many washes. Besides, do I really need 15 T-shirts? Most of which are from concerts I saw in 2006?

“No, they’re not necessary–but isn’t it funny how we all tend to wear certain things out of our closet constantly and we don’t touch the other part of our closet?” points out Nicole.

I am guilty of this. I have a whimsy denim dress with floral patches hanging in my closest I like, but haven’t worn in ages….and yet, I live in my fave black leggings and a grey GAP tee. I’ll even Febreeze them and wear them two days in a row. (Hey! Old college habits die hard.)

Declutter your house and your mind

Cleaning out your closet is also a great way to just clear out clutter—from your home, and your mind. Knowing this can make tossing easier.

I once heard (and I don’t know from who—I will just say Oprah for the sake of it) if you haven’t worn it in a year, you’ll never wear it again. I make that my mantra when cleaning out most of my clothes so I’m not hanging onto pieces that are just collecting dust.

Sell, donate, or swap

“I don’t like clutter—so when it starts getting crazy, I know I have too much in my closet. Time to get rid of the stuff I don’t wear!,” says Nicole. “What’s great now is that there are apps where you can sell your clothing, which you can use for cleaning motivation– or you can just donate items. There are so many new options now.”

Apps for selling clothes:

• Poshmark
• ThredUP
• Depop
• Mercari
• OfferUp
• Curtsy

Another great option: Hand it off to your bestie. Trading clothes with friends is a clever way to toss your crap and upgrade your own wardrobe.

Give upcycling a try

And, of course, I like to upcycle and recycle. I’ve dressed my kid’s large teddy bears in old, shrunken college tee’s of mine, and used ratty clothes as dish rags (including cut-up cotton leggings) that I store in a “junk” bin under the sink. I’ll even cut up old shirts and leggings—only cotton ones—and use the to apply my Witch Hazel (astringent) at night because I find when I pat the fabric on my face it’s just as comfortable and soft as a cotton pad.

In a pinch, you can even use old, stretched-out tee’s as pillowcases; which I’ve done when my kids had an accident (or even food poisoning…) in their beds and I can’t seem to find a fresh, new, clean pillowcase at 4am.

Didn’t I say old college habits die hard?