A closet clean-out sounds deceptively simple: pull everything out, make a few decisions, and donate what you no longer wear. In reality, it is rarely that straightforward. Clothing is deeply personal. It carries memories, aspirations, guilt, identity, and sometimes an unhealthy amount of hope, which is why decluttering a wardrobe can feel far more emotionally exhausting than organizing a kitchen cabinet or garage shelf. If you've ever started a closet clean-out only to end up surrounded by piles of clothing and questionable life choices, you're not alone. These four strategies will help you move through the process with more confidence, more clarity, and hopefully, a little less regret.
"After all, life is too short to wear ugly clothing."
Step 1: Address the Emotions Head On
Clothing holds emotion. If you don’t believe me, pick up the bridesmaids dress you wore to your best friend’s wedding, or the shorts you wore on a first date with your first (or most recent) love. As you slide down the zipper, memories begin to flood back. Details you thought you had forgotten become clear as you step into it.
To say clothing doesn’t hold emotion would divorce us from reality: we use clothing to explain ourselves to others. When we get rid of a piece of once beloved clothing, we are faced with acknowledging a piece of ourselves has ceased to exist. When I quit my corporate job after ten years, I carefully boxed up my office wardrobe and set it aside. It was a curated collection of items I once loved, which once gave me instant confidence. I can still remember how good I felt in my red crepe sheath, standing in front of 700 people. The good memories are folded up alongside the bad, representing the life I no longer lead.
While some of us are more nostalgic than others, we all approach clothing with a less than rational mindset. We give value to specific items because they were expensive; others because you got them on a steep discount, a story you love to retell to anyone who will listen; and still others were gifts from friends, husbands, or long-gone lovers.
When performing a closet clean-out, do not try to deny the emotional ties we have to certain items. Acknowledge it, spend time in it, and then ask yourself, “Would the person I am becoming wear this?” Don’t let your current wardrobe help you cling to a reality that no longer exists. Instead, thank it for the special role it played in your life, and set it aside. You’ll be surprised at how freeing it is.
If you are extraordinarily nostalgic and struggle to get rid of anything for fear of regret, move on to Step 2. Quickly.
"Pick a friend with a bit of sass, who will…tell it to you straight…”
Step 2: Leverage the Buddy System
It is a classic strategy for a reason. If you have a loving friend/mother/sister/co-worker who you trust, enlist their help with the clean-out. Get their opinion on what items you should keep and what needs to be tossed. The benefit of an objective third-party is they do not have the same emotional or financial connections to your clothing as you do. Your friend does not care who gave you the lime green sweater or how much it cost. She only cares that it is ugly, and you never wear it. Word to the wise: do not take the easy path and pick the friend who thinks you look amazing in absolutely everything. Pick a friend with a bit of sass, who will praise you when something enhances your beauty or tell it to you straight when your fifteen-year old bandage dress isn’t slapping quite the way it used to.
Even if you do not have someone in your orbit who fits the bill, take pictures of yourself in the item you are debating about and send it to your friend across the country to get her opinion. Or, sleep on the decision and look at the photo again the next morning. How does it make you feel? Does it make you smile? If yes, boom. Keep it. If the answer is no or “meh”, toss it. Use your resources to help you build the best closet of your life.
“Would the person I am becoming wear this?”
Step 3: Time it Thoughtfully
For those of us who menstruate, commit to a closet clean out at the right time in your cycle: your mid to late follicular phase. I’m not joking. Please, for the love of Cristobal Balenciaga, do not clean out your closet in your luteal phase.
If you do, the best case scenario is you collapse halfway through in tears, overwhelmed by the surrounding piles of un-edited clothing, and spend the next six hours eating your feelings and watching 1995’s Pride & Prejudice for the seventeenth time. Colin Firth is the only Mr. Darcy.
Worst case scenario: seized by a hormone-fueled conviction your closet has been holding you back, you bag up every piece of clothing you own, and, to confirm your deep commitment to the process, you immediately drive the bags to the local donation center, never to be seen again.
Huzzah! Your new life begins today. The chains of yesterday have been shed!
By late evening, you have fallen asleep on your laptop with fourteen open shopping tabs and thousands of dollars of clothing headed your way in 3-5 business days. The next morning you awake exhausted to a gapingly empty bank account, with nothing to wear, and a deep sense of disbelief.
Ask me how I know…
Start a closet clean-out when you are in your mid to late follicular phase. This is when you are starting to feel more powerful, energetic, and confident. Your closet clean-out will reflect this. Starting in this phase allows you to reduce the noise in your head and focus on what you really need for your stage of life. Closet clean-outs are tiring and time consuming.
Give yourself the best possible chance to make it successful and simplify your life by choosing the right time of month to dive in.
Step Four: Be Realistic About Your Current Size
I have a pair of jeans hanging in the back of my closet which are two sizes too small. A pair I am convinced I will probably never be able fit into again…but there’s still a chance that I will lose those fifteen pounds and return to my pre-baby, pre-Covid body….
It is time for me to be realistic about my body and the size I am today. This means getting rid of the jeans from high school. You may not be the exact size you would like today, but, if you are anything like me, I felt the same when I was a size 6 and wished to be a size 4 or when I was a size 8 and longed for the days I could fit into a 6.
It is the never-ending cycle of discontent we need to break.
The best way to feed body dissatisfaction is to refuse to invest in clothing for your current size and shape. Wearing cheap, frumpy clothing guarantees you feel uncomfortable and self-conscious. I speak from lived experience.
Be willing to invest in your appearance, regardless of size. Refusing to do so is the same as saying you only deserve beautiful things when you fit into a specific size category. What a giant load of bollocks.
For those of you shaking your heads and thinking “not me”, I see you over there in the corner. Ladies, this is a two-way street. Those old maternity clothes or larger sized jeans you have not worn in years need to go. Donate them. Gift them. Give them away. Let them have another life with someone who needs them more than you do. If you change sizes in the future, the chances are your style has changed with it. You will want to buy something fresh and new to feel fresh and new. Do not fall into the guilt trap of, “Well, I could wear these old jeans…”. Life is too short.
A great wardrobe is not built by accumulating more clothing. It's built by making thoughtful decisions about what deserves to stay. Every piece you remove creates more space for the clothing that serves your life as it is today. Honor the memories your wardrobe holds, but don't allow them to dictate your future. Dress who you are becoming. Your closet should support your life, not preserve a museum of every chapter you've ever lived. When you clear away what no longer belongs, you create room for the things that do. At the end of the day, and I may have forgotten to mention this, life is too short to wear ugly clothing.
Until next time or my next ovulation,
Elise
