The change of season means it’s time to take a fresh look at your wardrobe and shed any items that are bringing you down. I went through my closet this weekend and I feel great about it. Now my closet only contains items that I really want to wear. Here are some guidelines that can help you tackle the project in style.
Before You Begin
Do your laundry. Make sure all your clothes are clean, present and ready for evaluation.
Set aside a single chunk of time. This job is gonna take at least a few hours and create a big mess. Set aside 3-4 hours, focus on the task completely and get it over with. You want to operate quickly and decisively and not let the chaos spill over into the next day. I chose a time when my husband was out of town and I could try on clothes and throw stuff all over the place in peace.
Plan for your rejects. I basically had two piles for my discards: trash and donate. But you may need another category—like repair, consign or up-cycle—depending on your stuff and priorities. Just make sure you have containers ready for each destination, because your cast-offs are leaving the house today.
Assess What You Have
Start with the low lying fruit. Toss anything ripped, stained, broken or tired looking. You can’t donate underwear or swimsuits, so throw those away as well.
Comfort is key. No matter how great an item looks, if it feels tight, stiff or scratchy, say bye-bye. Being in style does not require you to be in pain. No surprise, uncomfortable shoes were at the top of my donate pile.
Decide when enough is enough. We tend to buy a lot of the same items. Do you really need 15 white blouses or 18 different pair of jeans? Of course not. Try them all on and weed out the less flattering styles. I discovered I owned 14 black short-sleeved tops and five of them weren’t great. Paring down areas where you have a surplus will help you have a more refined wardrobe and more room in your closet.
Take a picture. Your cell phone camera is a really helpful tool. A photo helps you be more objective when evaluating an outfit than looking at your reflection in the mirror.
Style pieces in new ways. If you aren’t sure about something, dress it up or down and mix it with items you really love. You may find a whole new way to wear the piece. I found several items I haven’t worn much that, when styled differently, are worth keeping.
This long pleated dress is less overwhelming when broken up with the white sweater and booties. 
The skirt is a classic and looks good with basics. Plus it has pockets. Keep! 
These graphic stretchy pants work better dressed down, with my fave sneaks and tee. 
I’ve been waiting for a fancy occasion to wear this dress, but I’m just going to take it out to lunch.
Break up with old loves. Over time we grow, we shift, we develop! Our clothing should reflect who we are now. I’ve written about how I’m saying no to ripped jeans and high heels these days. But going through my clothes made me realize I’m also over my crush on flowing, flouncy, boho blouses. Here are three tops I’ve worn a lot but just aren’t me anymore. Hopefully they’ll be a match for some other gal.
Ignore the money (for now). It can be upsetting to realize you spent a lot of money on things you haven’t worn, but at this point, it doesn’t matter how much you paid for an item. It’s a sunk cost. If you haven’t worn the piece in a year and still aren’t feeling it, let it go.
Put everything away and congratulate yourself. Now you should love or use everything that’s hanging in your closet, and have some new outfit ideas to boot.
After You’ve Sorted
Do the donation run right away. At least load up the car. You want these clothes out of sight and out of the house so there’s no risk of rethinking or rescuing!
Learn from the experience. Cleaning out your wardrobe can be emotional. Clothes are so personal—you may feel sentimental, regretful, guilty or sad. Go ahead and feel your feelings, but then try to take some positive lessons from the experience. For example, I realize that online shopping doesn’t serve me well. Many of the things I got rid of were “deals” I’d bought online. They were okay, but I just didn’t feel great in them. Turns out I’m much more discerning when I shop in person. I either need to stop buying things online or get better about returning the duds.
Enjoy your clothes. Now that you’ve done all the hard work, have fun wearing what’s in your wardrobe. Don’t save things for “special” occasions. It’s okay to wear an outfit simply because it makes you feel happy.
I hope these tips are helpful! There’s a whole other post about how to organize your closet, but I haven’t mastered mine yet, so it will have to wait. If you have suggestions about cleaning out your wardrobe, I’d love to hear.
Here are a couple other posts you might like:
Fully Fabulous 
Your timing is perfect. I was just cleaning my closet. I learned I have 20 white t-shirts. Ridiculous. Great advice from you–although I still like that orange top you are donating. If you haven’t already donated it, you should rescue it!
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Too late!! It’s gone! But thanks for reading and too funny about our closet clean out timing.
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