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The Well Dressed Life Wardrobe Challenge 2022: Week 2

The Well Dressed Life Wardrobe Challenge 2022: Week 2
4 Weeks to a Better Wardrobe - The Well Dressed Life

Happy Friday, Ladies! 

We’re jumping into week two of our Wardrobe Challenge. First, a big thank you to everyone who has joined our private Facebook group and took the time to post their Pinterest style boards and lifestyle breakdowns.  

I promise, the more you participate and chat with your fellow members, the more you will get out of the process. 

There have already been some big takeaways after week one, and they are exactly what I was hoping they would be!

If you are just joining us, or are running behind, don’t worry. 

You can go at your own pace and still post your thoughts and interact in our group’s comments. 

Be sure you finish each challenge before moving to the next. This week has two challenges designed to refine your style and make editing your wardrobe not so overwhelming.

Wardrobe Challenge Week 2:

Pinpoint Your Style and Start Your Edit

Challenge #1: Edit Your Pinterest Board

This part of the challenge always creates the most conversation. You might be thinking that you need to pick a style and commit to it. We’re told we are either “classic,” “trendy,” or “boho.” Like we have to pick a lane and stay there. 

But the truth is we are all a unique combination of many things. 

For example, I used to think I was “preppy.” 

But I’m not.

I like elements of preppy style. I never pass up an opportunity to monogram something, and a good chunk of my wardrobe is from J.Crew.

But I’m not too fond of bright colors and prints; I prefer saturated neutrals and better fabrics. 

After going through this very process for several years now, it’s clear that my style is classic and modern with a twist. That “twist” is usually an interesting detail, splurge-worthy piece, or an unexpected personalized element – like a monogrammed bag or bold accessory.

To help you with this, go through your Pinterest Board and only keep the image you LOVE. 

You must LOVE every pin. (I know! It’s hard.)

The Difference Between “Liking” and “Loving”

It’s not just what you like, but what you want to live your life in. 

You can appreciate all different styles, but narrowing it down to the ones you want to wear all the time and starting to understand how you can adjust your style to your life is the point. 

Take a few minutes to write down what you dislike, like and love. Mine is below:

Remember, this is personal. I dislike ruffles on me; someone else can look great in them. 

Doing this exercise forces you to think about your preferences and ensure your wardrobe mixes and matches well, and you always look (and feel!) yourself. 

Find Your Common Threads

Next, review your edited board and look for commonalities and consistencies. It might not be abundantly clear, but stick with the challenge; it will start to show itself.

You can keep pictures of outfits not quite suitable for your body type; we’ll get to that later. Your board is pure inspiration.

Any style can work for any body type with proper adjustments.

What we’re looking for here is a theme.

Some a-ha’s you might have:

  • You pinned lots of jeans and pants but have a ton of skirts collecting dust in your closet.
  • Maybe you pinned a dozen monochromatic looks yet own a ton of patterned tops and dresses.
  • Do the outfits on your board have scarves and accessories, but you never incorporate them into your daily outfits.

If these are the revelations you have as you finish up this part of the challenge, you are right on track!

Challenge #2: A Quick Closet Edit

You can do this next step all at once or over a few days; it depends on how much you have in your closet.

Set up a workspace in or close to your closet. Designate four piles:

  1. Keep:  For anything you know you love, use regularly, and fit in your style.
  2. Mend:  Keepers that need to be tailored, cleaned or repaired somehow. 
  3. No’s: Items that do not help you achieve your desired style. 
  4. Maybe: Use this as a parking lot for items your undecided items.

Having a rolling rack for this exercise makes it easier to stay organized. I use mine for the “keeper” pile.

Next, take your Pinterest board or other inspiration pictures into your closet.

While you’re in your closet, ask yourself these questions and try to come up with an answer:

Is your current wardrobe reflective of the style you love?

If not, what is your motivation for making purchases? (Sale price, impulse, need, etc.) 

What do you have more of, basics or trends?  

For example, my Pinterest board is primarily neutral and solid colors, yet I had at least a dozen printed blouses and tops hanging in my closet when I first did this exercise. 

There was nothing wrong with them, except I don’t like many patterns, and I wasn’t wearing them.

So why do I keep buying them?

 In my case, I needed variety. I was also using Stitch Fix and the time and kept many pieces they sent only because they were okay and fit.

Once I completed the exercise, I permitted myself to let go of what didn’t fit into my style.

You may not have many things in your current wardrobe that reflect your style. (If you do, you’re way ahead of most of us!)

It’s okay to feel frustrated. Take a deep breath and trust the process.

These steps will allow you to discover what you like, understand your decision-making process when shopping, and eventually help you fill your closet with items you can’t wait to wear.

The process of creating a cohesive wardrobe is not immediate. 

That’s why so many readers do this challenge every season. It takes time to curate your look, find the pieces that work best for you and, of course, work those purchases into your budget.

But after this challenge, you’ll be off to a great start.

Quickly Edit Your Wardrobe

With your inspiration pictures as your guide, QUICKLY, go through your wardrobe. 

Hold every piece up and ask yourself, does this get me to where I want to be?

If your answer is “yes,” put the item in your keeper pile or rolling rack.

If your answer is “no,” put it in your no pile.

If you have no idea or don’t want to deal with it, put it in the maybe pile.

We’ll deal with those items next week.

 Do this quickly. The maybe pile is there to take away any pressure.

You will likely have to keep a few pieces that are just okay so you can get dressed in the morning. 

Put these in the undecided pile too. The most important part of this exercise is to see if or how much of what you are buying reflects your style.

Once finished, go through the no’s and decide how you want to process them. You can donate, resell, recycle, or they go right in the trash.

Hang and fold everything else.

Put your undecided pieces back in your closet, behind the pieces you love, so your favorite items are the first thing you see.

Please don’t focus on organizing anything yet (you can guess where we’re going next week).

Repeat the same editing process with your shoes and accessories.

Are you just getting started? Be sure to follow each challenge in order. For week one, follow the link below:

The Well Dressed Life Wardrobe Challenge: Week 1

And join me on Sunday, April 10th at 7pm EDT for our Week 2 LIVE over in our Facebook Private Group. I’ll recap Week 1, set you up for Week 2 and answer any of your questions.

If you can’t make, you can catch the replay posted once the LIVE wraps up 🙂 

52 in 2022!

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Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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The Well Dressed Life Wardrobe Challenge 2022: Week 2

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Mary Ziebell

Monday 13th of September 2021

Greetings! Of all the fashion bloggers I follow, I truly love this one the most. I'm enjoying this process of defining my style and purging the closet. My issue is that I have registered several times for the free Wardrobe Checklist and have not gotten anything sent to my email. Before you ask, I've already looked in the Junk and Spam folders. What am I doing wrong? I really thing this would be a useful piece of information! Thanks all!

Elle Waters

Tuesday 9th of March 2021

This is so helpful. I am going through all the parts and am loving it, Thank you for sharing!

PatC Fields

Thursday 18th of February 2021

I put together a board and think I know how I will be putting outfits together. It has already helped. As for lifestyle, there are 2 items. I am staying at home or traveling/going.


Friday 25th of September 2020

I bought a cloths rack and plan of going through my closet tomorrow. Will today’s Face Book live class be posted to Facebook. I couldn’t figure out how to join in. Love the group!


Thursday 23rd of January 2020

My aha! Was when I realized I had blouses from years past that I haven’t worn for ages. I kept them to wear with a pant style that has long since disappeared. I was keeping them just in case. Of what I don’t know, but there they were covering up items I wanted to wear and couldn’t find. I also found several short cap sleeve tees. They don’t not look well on me. Time to pass them on.

Megan Kristel

Saturday 25th of January 2020

Such a great take away! Thank you for sharing!!!

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