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Are These Wardrobe ‘Shoulds’ Keeping You Stuck?

I bet like many women, you have a running list of wardrobe ‘shoulds’ in your head. Do any of these statements sound familiar?

  • I should clean out my closet once and for all.
  • I should get dressed for the day even though I feel like staying in my yoga clothes.
  • I should figure out why I can’t seem to get out the door without leaving the bed piled high with rejects.
  • I should figure out why that new item I was so excited about doesn’t seem to work with anything else I own!
  • I should figure out what I’m doing with those suits I used to wear to work.
  • I should get those shoe repairs done so I can wear them again.
  • I should be able to put a decent outfit together by now.

Any way you say it, it sounds like a giant headache waiting to happen.

Things may not be the way you’d like them to be, but talking to yourself like you’re ‘less than’ for not having it all together or comparing yourself to seemingly perfect images on Pinterest or Instagram is not going to help you feel better or get dressed more easily.

It’s so easy to get bogged down in the ‘shoulds’ that you never get beyond it and simply live day to day with frustration and dissatisfaction.

Let’s look beyond the ‘should’ statement. Do you see an underlying desire? Do you have a longing for ease (that’s a biggie), time for yourself, or more fun?

Let’s see how you can begin to eliminate the shoulds and focus on the underlying desire.

  • I’d like to be able to find things easily in my closet.
  • I’d like a few well-put-together outfits.
  • I’d like to wear these shoes again.
  • I’d like to find someone who’d appreciate those suits I don’t use anymore.
  • I’d like to feel great about how I look outside of yoga class.

With shoulds in your rear-view mirror, let’s move in the direction of satisfying your desires.

Here are a few guidelines to keep in mind (and feel free to add your own list).

Keep your expectations low so your successes have a chance of showing up.

  1. Before you have a closet full of put-together-outfits, you need to start with just one. Can you give yourself the gift of time and create one outfit using an item you love wearing? One outfit equals success. If this is the biggest issue you have with your wardrobe, keep your focus on this desire to have ready-to-go outfits. Next week you could create a second outfit. Do you see how they’re going to add up? And it will give you invaluable information about where you have holes in your wardrobe.
  2. If you have shoes or handbags that need repair, your first simple step would be to put them in a bag or box and take them to your car. You’re already one step closer to being able to wear them again! On another day, drop them off at your local shoe repair shop. Easy does it. In a week or so you’ll pick them up. What joy it will be to have them back in your closet and ready to wear!
  3. If much of your closet is devoted to clothes that don’t suit your lifestyle anymore, you’ll benefit from removing them so you can focus on what you can be wearing right now. Maybe your first step is deciding where you’ll take clothes you don’t use. Decide to tackle that decision first. How about a church, women’s shelter, or an organization that helps others get back into the workforce? In fact, some charities will even pick up at your home. Talk about easy!

And, if that feels too scary, then just pack them away in an empty closet or plastic bins. The most important thing is to get them out of your working closet. Thinking about the win-win this will mean to you and the charity you’re helping out (if you donate some or all of the clothes) will give you the energy to follow through.

The thing about creating a wardrobe that makes getting dressed easy is that you do need to devote some amount of time and energy to it in order to get results. If you find yourself starting to make progress and then you get stuck, confused or overwhelmed, having help and getting answers to your questions will make it all feel easier.

With an experienced professional at your side, who is compassionate and understanding and who can help you accumulate new information that will help you navigate your wardrobe ‘shoulds’ down the road, you’ll feel like you can conquer your wardrobe woes with confidence. Talk about good self-care!

If you are longing to feel confident and beautiful in the clothing choices you make I have good news. You can! And, you can do it without shedding pounds, sacrificing comfort or compromising who you are. I’ve listened to women for years and have taken their biggest style frustrations and addressed them in my live ‘Create Your Personal Style in 6 weeks’ Masterclass. Here’s what Bethany from Florida has to say about her experience in the class: “Ginger is the answer to my prayers. I didn’t believe my wardrobe could be anything other than a burden and didn’t realize how bad it was until I met Ginger and started to feel good in my outfits. I have been amazed and forever grateful for all I’ve learned with Ginger.” Imagine how it will feel to realize your dream of eliminating stress and instead feel deeply satisfied and delighted every time you get dressed! Get on the waitlist now so you can be the first to know when the class is open for registration again.


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Ginger Burr is a fashion stylist and personal shopper serving clients worldwide from metro Boston.