How to Finally Clean up Your Wardrobe

If you’ve read any of my style posts, you know I’m a big proponent of dressing to project your most confident self. In my last post on shining from the inside, I asked:

How often have you been irritated and running late because you don’t like anything in your closet?

I faced the “what to wear” dilemma so often that it became a part of my life. Every wedding, brunch, or happy hour carried an undertone of dread. This feeling doubled if the “event” was right after work. I’d either pack an alternative outfit or shop for an entirely new outfit during lunch! It was stressful, expensive, and dissatisfying – I rarely wore those outfits again. If there were photos (which, let’s face it, are nearly inescapable), I would actually worry that I was repeating an outfit too soon. Somewhere along the way, I realized that even daily dressing had become a chore. My closet was full of novelties that were “cute” individually, but didn’t hold together as a wardrobe.

Here’s the secret: stop worrying about who’s seen you in what.

Instead of dwelling on the wave of self-consciousness when I repeated something, I started paying attention to why I wore certain things so often. We all have our staple pieces that we live in! The photo in this post (one year ago) was taken over three years ago and I still wear that sweater regularly.

Rosie agrees: you should wear what you love!

This, and the other pieces in my regular rotation brought me clarity:

It’s easier to get dressed when you like love everything in your wardrobe.

BUT Nostalgia =/= Love.

Sentimentality is the foundation of the “my stuff” mentality. (My bubbles!)
We have to learn to separate the “thing” from the memories; Possessions can come and go. The experiences we had with them are ours to keep. Selling or donating pieces that no longer fit or that you haven’t worn in years gives someone else a chance to make a memory.

When you’re caught up in nostalgia, it’s important to question your logic.

The easiest way to start letting go is to ask yourself four simple questions:

  • Does this fit?
  • When did I last wear it?
  • How soon will I wear it again?
  • Is this me, now? (Would I buy this if I saw it now?)
  • Do I feel fabulous/confident/beautiful?

These questions have helped me let go of a lot over the years, but your wardrobe should evolve with you, so I like to check in every six months. [It’s also been a full year since I committed to a healthier lifestyle (yay!) and I’ve reduced two sizes.] Living in a studio, it’s hard to justify keeping clothing that I like but no longer fits.

Don’t mistake the message – I’m not suggesting you throw it all out and start from scratch every six months. Most of us can’t go on a good ol’fashioned 80’s sitcom musical montage shopping spree.

So how do you revamp your wardrobe without spending all of the money?

Like everything here on TBBL, there’s a strategy – start with what you have. A closet purge isn’t only about getting rid of things, it’s also about rediscovering forgotten pieces, and to do that, you have to put it all out there.

Step 1: Make a giant pile.

This is going to sound scary, but empty out everything. Your closet, your drawers, that hamper or chair that you pile clothes on. Put it all on your bed and separate it by category: tops, bottoms, dresses, tights, etc. While you create the piles, set aside the pieces that you know are completely beat up, damaged, or stained.

Pro tip: This is also your chance to clean up your storage system and invest in slimmer, matching hangers and boxes! Here are some of my faves:

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Step 2: Start the party!

Whether you start or skip on starting a “trash” pile, the next step is the longest part of the process: trying it on. (Yes, all of it.) If the task seems impossible, that’s more reason to commit to it. There will be pieces that you know have always fit weird, or are a gift in an unflattering color that you’ve never liked. Trust your instincts: if your immediate reaction is not wanting try something on, that’s grounds for moving it into the “out” pile. You can also skip the well-loved pieces that you know fit great (because you wore them last week), and those can start your “keep” pile. To make this part less painful, put some music on and invite a friend over. It helps to have someone there to keep you accountable and give an objective eye.

Fun fact/TMI: To make the process less painful, allow yourself one ratty keeper 😉 I’ve got a torn PJ that’s survived a few rounds, myself.

Step 3: Package it up.

By this step, you’ve got four piles – Keep, Discard, Sell/Donate, Fix.

First, throw your donate/sell pile in the wash. While that’s going, gather up the fix pile and place it somewhere you can’t escape. I’m guilty of setting aside an item for repair and finding it again months later – taking up space and still not wearable. You want each item in your closet to be accessible at any moment, so keep this package in your sight so you don’t forget to complete Step 4.

Next, commit to not throwing the “Discard” pile in the actual trash. Instead, check for textile collection efforts near you (like Wearable Collection in NYC.) Once your donation clothes are clean, pack them in a bag and again, keep it in plain sight. If you’re planning to sell any items, check out this quick guide I put together for easy “product” photography (I’m a big fan of Poshmark!)

Once the outgoing piles are ready to go, start the process of returning your keepers to their rightful place. Don’t get too excited, they’re in the clear just yet! I picked up this handy tip from PopSugar: hang everything in your closet backwards until you wear it. Once you’ve worn it, turn the hanger around and it’s safe (for now). Any hangers that aren’t flipped in six months are headed for the Sell/Donate pile.

Step 4: Sell/Donate/Drop off

Chose a day to hit the most satisfying part of this process – reclaiming your space! Taking the donate pile to your local Goodwill* and dropping off the fix pile to the tailor in one day is a complete win. Treat yourself to a little celebration (did someone say gelato?) and enjoy the freedom of a closet that is built to flatter you no matter what you wear.

(*You can also donate to my current favorite, Schoola in their efforts to support the Malala Fund.)

It’s a big commitment, but there’s no price on looking and feeling your best!

Unless you know an organization professional, no one is going to do this for you. Embracing your style and refining your image is a commitment that you deserve. It’s not selfish to set a day or two aside to free yourself from an imbalanced wardrobe. If you’re feeling overwhelmed and want some guidance to put this plan into action, I’ve made a Closet Clean-up guide for you! Download it here:

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I want to hear from you!

  • How often do you go through your closet?
  • What’s the one piece you can’t live without?
  • What’s your guilty forever keeper?