Sometimes our day turns frantic before we even make it out of the house! We open our closet, pull out one item of clothing after another only to find that nothing works. Nothing looks good. Nothing seems to fit right. Nothing makes us feel great about our looks and our bodies. As a result, we end up with items tossed in the floor or over a chair while we hunt for something that “will do.”
As a result, we end up leaving the house (probably) late, frustrated, and feeling like a frumpy failure because we don’t look or feel good in what we’re wearing. And we’re most likely crossing our fingers that no one really takes the time to look at us too closely because we didn’t like what we saw in the mirror. In my case, this also made me more likely to snap at the kids and be grumpy before I even managed to get to work.
This is no way to start your morning!

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I used to joke with my mom that I wanted Stacy and Clinton to come ambush me and put me on their show What Not To Wear. I would have happily put myself in their capable (and stylish) hands and been thrilled for the chance to toss out everything I own and start over – with the $5,000 from the show, of course. Alas, Stacy and Clinton never showed up.
But since they didn’t, I finally figured out that ending the daily battle with my wardrobe was up to me. Maybe what I learned can help you end the war sooner and with less frustration.
Analyze what’s wrong with your clothes
Our first step to creating a wonderful wardrobe is to get rid of the clothes that aren’t working for us. You know the ones…you pull them out, take a look at them, and hang them back up in the closet.
Unfortunately, hanging the rejects back up doesn’t solve your problem. It will be just as hard to get dressed tomorrow.
To keep from repeating this scenario day after day, you’re going to have to figure out what’s wrong with your clothes. Why do you hate certain pieces? Sometimes it’s because our wardrobe literally doesn’t fit us anymore. Weight fluctuations and body changes can turn once loved pieces from “Wow!” to “Ho Hum” or even to “Yuck!“
This calls for a complete closet clean out. I know it hurts – I’m right there with you. I’ve been dealing with a major case of frustration with my clothes and closet ever since I quit my job and began working at home.
First, go through everything in your closet. Some pieces will be easy…you just don’t like the item anymore. Start a pile of rejects.
But some pieces are going to be much harder to make a decision about. You’ll have to ask yourself some questions about these pieces.
Getting your wardrobe under control is going to be a bit like a boxing match: there will likely be several rounds till you get to the winners.
Round 1: the easy elimination round
Admittedly, you’ll make the fastest progress here.
Before even taking something off the hanger, ask:
- Does this still look good? Some pieces just don’t hold up well after repeated washing and drying cycles.
- Is it stain-free and in good condition? Don’t convince yourself that you’ll always wear that shirt with a jacket so no one will ever see the slight stain. Save yourself the hassle, worry, and embarrassment and just get rid of it!
- Is it still in style or of a classic style?
- Do you still even like it? Our tastes change over time. Something we loved a few years ago may just not do it for us now. That doesn’t mean it wouldn’t be perfect for someone else though so don’t feel guilty for letting it go.
Anything that doesn’t get a yes response to each of these questions automatically goes in the reject pile. No sense wasting any more time or effort on these pieces.
Round 2: trying things on
Now it’s time for things to come off the hangers and begin the fashion show.
- Does it fit? And I mean does it really fit? Sometimes we tell ourselves that something fits ‘well enough’ when it’s either a little too tight or too loose. If something is too loose, can it easily or inexpensively be tailored to fit? If so, it might be worth saving IF you adore the piece and it’s a classic style. If it’s a trendy piece it’s probably not worth sinking any more money in to it. And if the piece is too tight…well, just because we can squeeze our rump into something doesn’t mean we should (you know what I’m talking about!). Unless you’re on a serious diet or your weight regularly fluctuates, get rid of this.
- Does it flatter you and make you look your absolute best? I don’t know about you, but I’ve definitely put on clothes that fit but just didn’t make me look good. Maybe they emphasized a body part I didn’t love (we’ve all got them). It’s also important to ask if you feel comfortable in the piece. Are you going to be constantly checking to see that your neckline isn’t exposing more than you intend? Does it itch, irritate or bind anywhere? There are lots of ways a piece can be unflattering and if you’re not comfortable….it’ll show.
Your reject pile should be getting bigger.
Round 3: Determining the winners
This is the tough round. This is where you’re getting down to the essence of what is working – and not working – in your closet. For me, this is the hardest part and the one I dread.
- Do you love it? If you found this in a store today, would you still buy it?
- Does this piece reflect where you are right now in your life? Is it too casual or too corporate? As our life circumstances change, our wardrobe needs change as well. This one can bring all sorts of emotions bubbling up to the surface which is why it’s often so hard to part with certain pieces.
- Are they appropriate for your activities? If you’ve re-entered the job market you’ll need different clothes than if you are at home most of the time.
- Does it go with several other pieces you already own?
- Does this make me look and feel fabulous?
Whew! Space at last
Now that you’ve got space cleared in your closet you won’t be wasting time pulling out clothes that don’t work for you. You can now take inventory to see what you’ve got and what you still need.
Now it’s time to figure out what looks great on you so that you don’t make the same old mistakes.
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Invest in yourself
While a wardrobe course is not free, neither are bad purchases. Having clothes that just hang unworn in your closet is expensive in terms of money spent, time wasted getting dressed, and the toll on your self-esteem.
A good course will help you figure out what styles work well on your body type and what colors compliment your coloring. Once you know these two pieces of information, you can begin to salvage what IS workable from your closet. This allows you to know what you already have and what needs to go on the shopping list.
Resources to help you look your best
I’ve been through the Dressing Your Truth course (loved it!) and Adore Your Wardrobe (awesome course!). The way I look at it, a good course is an investment in myself that will pay off when I don’t buy the wrong things anymore.
But if you’re not in the market for a course, there are lots of great books to help you up your fashion game, learn how to shop, and determine what looks good on you.
Dress Your Best: The Complete Guide to Finding the Style That’s Right for Your Body – Clinton Kelly & Stacy London (read this – loved it)
Oh No She Didn’t: The Top 100 Style Mistakes Women Make and How to Avoid Them – Clinton Kelly (read this – loved it)
Quintessential Style: Cultivate and Communicate Your Signature Look – Janna Beatty & Sharon White (haven’t read this but want to)
40 Over 40: 40 Things Every Woman Over 40 Needs to Know About Getting Dressed – Brenda Kinsel (own this – love it)
How Not to Look Old: Fast and Effortless Ways to Look 10 Years Younger, 10 Pounds Lighter, and 10 Times Better – Charla Krupp (own this and love it)
You are worth it!
It takes time, energy, thought, and planning to build a wardrobe you love. Getting the duds out of your closet is the first step. And you don’t have to rush out and buy a ton of new clothes – focus on the basics first. Just be sure that the pieces you add from here on out are pieces that you love, that make you look great, and that you feel wonderful wearing. You’re worth the investment!

I help older women get past their fear and mindset issues so they can create a plan to pursue their goals and dreams.
These are great tips. The purge is always the hardest part for me!
For me too!
I’m very guilty of letting clothes linger decades longer than they should. Your post gave me inspiration to tackle some tough “final goodbyes.”
Hi Laurie! The hardest wardrobe for me has been dealing with the clothes from my former professional life. Every wardrobe holds some emotion that we have to come to terms with and it’s hard.
What great resources for changing your wardrobe. I keep waiting to take off a few extra LB’s but it’s a slow process. Getting tired of too much black. I want some color.
I think a lot of us postpone updating wardrobes for the very same reason. But we deserve to feel and look good during the process – and it’s motivating.
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All so true. I went through this process with the Adore Your Wardrobe course. I had an almost empty closet and am now rebuilding. Don’t have near as many clothes, but they all look good and fit my lifestyle now. Great post!
It’s the buying and finding new clothes part I need to focus on the most. I get frustrated buying clothes and often settle for “good enough” when I’m at the store instead of really waiting to find those pieces that I just LOVE.
Me too! And I can’t tell you how many of those “good enough” clothes have ended up in the donation box.
Brilliant I’m well overdue a clothes sort and these are great tips thanks ????
So glad you enjoyed it, Catherine. I am making headway on mine but it is slow. However, I am dying to take the Adore Your Wardrobe course so I figure I’ll need room for the stuff that’s going to make me thrilled to walk into my closet.
This was a great post!! I’ve slowly been cleaning out my closet and secretly wishing that if I wait long enough Stacy and Clinton will come to me too!
OMGosh – Stacy and Clinton and being told what I need to wear would be a fantasy come true!
Great advice. I’ve been slowly getting rid of clothes that don’t fit me anymore. Your post reminded me to go through my closet once again. #overthemoon
Wouldn’t it be nice if it was a “once and done” kind of thing? Unfortunately, like every other type of cutter it’s one that has to be maintained to keep it from getting out of hand. Thanks so much for visiting, Tuula!
Your tips were wonderful. I think I can finally clean out my closet now!
I need to clean out my closet and have been putting it off to long! Great tips
Hi Patrick! I sometimes think my closet grows clothes when I’m not looking. It’s a continual process, especially when you love clothes (and I do!). Thanks for stopping by.