The Well Dressed Life Wardrobe Challenge 2021: 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. 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. 

Today, at 3 pm EST, I’m hosting another Facebook LIVE in the group to answer any questions you might have and get us set up for this week’s challenge!

There have already been some big takeaways after week one, and they are just 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 use 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 down to the ones you want to wear all the time is the point.

Doing so will help ensure your wardrobe will mix and match 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 right 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

How to Finally Let Go of Clothes You Don't Need

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

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

Keepers: For anything you know you love, use regularly, and fit in your style.

Donations: Something in good condition that doesn’t work for you but could help someone else. 

Undecided: Use this as a parking lot for items you’re on the fence about or not ready to part with. 

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 mostly neutral and solid colors, yet I had at least a dozen printed blouses and tops hanging in my closet when I first did this. There was nothing wrong with them, except I wouldn’t say I like many patterns, and I certainly wasn’t wearing them.

So why do I keep buying them? In my case, I needed variety. I was also using Stitch Fix and saved many pieces they sent 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 current 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.

Going through these steps will allow you to discover what you like, understand why you make certain decisions when shopping, and eventually 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

Now, with your inspiration pictures as your guide, QUICKLY, go through your wardrobe. (For more tips, check out our post 6 Steps to Clean out Your Closet in 60 Minutes) 

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

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

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

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

We’ll deal with those items next week. Do this quickly. The undecided 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. This is fine and expected. 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 personal style.

Once finished, put the donations in a bag and right into your car. Get them out of the house! 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

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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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10 thoughts on “The Well Dressed Life Wardrobe Challenge 2021: Week 2”

  1. Hi loving this blog. I turned 60 in June and desided to spend more time on my appearance so I did the first challenge in July. I finished the second challenge last month. These challenges make it more fun can’t wait for the next one. Thanks

  2. I am really into the idea of figuring out my style, and so far I have done all challenges of week 1 and the first of week 2.
    However I seem to be a little stuck….
    This is a link to my pinterst board:
    I pinned everything I liked and now narrowed it down to things I really like; but since in challenge 1 of week 1 we didn´t have to pay attention to body type or lifestyle/ budget I pinned a lot of things that will be too over the top for everyday life (I work part-time in an office; I occasionally go out or meet with friends, and I spend a lot of time in my own home)
    additionally I am not sure whats my “common thread”….

    any suggestions? I would really appreciate the help

  3. Hi Fellow Wardrobe Challengers!
    This was very interesting for me! My board was completely full of neutrals, a couple of dusty pastels, virtually no prints except for a handful of leopard, oversize plaid, stripe and blocking – all neutral. Meanwhile my closet is full of prints and colors! LOL!!! No wonder I can never find anything I want to wear! 😉 (BTW I’ve Kondo’ed my closet a few times.) I think the problem is that I LOVE color just not to wear it. My house is full of color. So weird. Anyway, that’s my Aha.

  4. 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.

  5. 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!

  6. 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.


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