The Well Dressed Life Wardrobe Challenge 2020: 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 help 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 don’t like bright colors and prints; I much 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!) like 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, when I first did this, I had at least a dozen printed blouses and tops hanging in my closet. 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 reflects 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

The January 2021 Wardrobe Challenge: Week 1

Wardrobe Challenge, Week 1
Four Weeks to a Better Wardrobe - Week 1

Ladies, today is the day you start to get your wardrobe in order!

Whether you work in or out of the home, have little kids at your ankles or grown adult children, are getting back in the workforce, or are blissfully retired and focusing on your passions, you want to look and feel great during whatever your season of life.

This four-week series is designed to help real-life women, of all shapes and sizes, with any lifestyle, within just about any budget discover their authentic style, where to find it, and how to wear it.

Be sure to go through every challenge, in order. This process was designed to build up each week. 

And join me today, at 3PM EST in our Private Facebook Group where I’ll go into even more detail about the challenge and dive into this weeks tasks. 

* UPDATED: You can view the LIVE playback here. 

So, who am I?

If you are new to our site – welcome! This Wardrobe Challenge is truly the cornerstone of our community. Before we dive in, a little about me so you can better understand the perspective I bring to my work. 

Wardrobe Challenge, Week 1

I was a wardrobe stylist for the better part of my career. I started my first company Kristel Closets, Inc, in 2007, which, at its peak, had three offices and a team of stylists on the East Coast.

After more than a decade, I moved on to focus on building our online business. But the experience of working with thousands of clients continues to influence my fashion and style posts today.

I take great pride in being a practical voice of fashion reason on the internet. All of the advice I share, especially in this wardrobe challenge, is based on proven tips and techniques I created to help our clients define their style, purge and organize their closets, and build a wardrobe that feels like them.

I’m also heavily influenced by real life. I’m a working mom to three amazing little girls. I get how busy and overwhelming life can be, how time is limited, budgets are stretched, and “me time” feels like an indulgence.

I’m 41, so I’m not looking to dress like a kid. Instead, I gravitate toward a sophisticated, classic style that works for my grown-up body and busy life. 

I navigate life happier and more confidently when I look and feel my best. Sometimes just putting on a pretty outfit or painting your nails can make a crummy day a little better.

It’s About You

Women want to look stylish and feel beautiful. But not everyone can clearly define their personal style or understand how to pull a look together.

I encourage you to use the next four weeks to focus on YOU. When this challenge is over, my goal is for you to have a clearer understanding of what you like and what will work for you, so shopping and getting dressed is easier.

Here’s How the Wardrobe Challenge Works:

Every Friday post for the next four weeks (starting today!) I will share a series of challenges to help you build a better wardrobe.

Take your time with each challenge. It’s great to do them in a week, but don’t worry if you can’t.

Just be sure to finish each challenge in order before you move to the next.

You can follow along with the group (join our private women-only Facebook group to interact one-on-one), or go at your own pace. You can also see more tips and videos on Instagram

These posts will live on this site for you to reference whenever you like.                                                                                                                                                                                                                              

Just trust the process, commit to the journey, and do this for yourself!

Week 1: Finding Inspiration and Your Personal Style

Challenge #1

In the early years of Kristel Closets, I would arrive at an initial appointment, which took place in our client’s closet. We started by talking about her challenges, likes, and dislikes. Almost every client would have trouble describing her style. 

It didn’t take long for me to realize that we needed a visual to articulate each client’s unique personal style.

So I created a series of pre-work for them to complete before our first appointment, designed to help the process move smoothly and efficiently.

I was always aware of our private clients’ investment when they chose to work with us, so this was a way to make sure we got on the same page as quickly as possible and spoke the same language.

Pull Inspiration Pictures

A big part of this pre-work was to pull inspiration pictures. I can tell you that the clients who took the time to complete this task had the most success.

Many of you are looking to streamline and simplify your wardrobe; others mentioned that they recognize style in others but have difficulty translating for themselves. And an overwhelming majority of participants say they have too much in their closets.

Without a clear understanding of your style, it will be a challenge to edit your wardrobe correctly.

By organizing inspiration pictures, we can create a filter that will help you purge your closet and shop better.

We recommend Pinterest to help organize these images, especially for this challenge. It’s a great place to search for and share ideas. Past participants have set up a board just for outfit inspiration. 

If you’re not on Pinterest, no worries. You can use magazines or catalogs. I like InStyle and Oprah magazine for this exercise. You’ll need them for next week’s challenge. So pour yourself a glass of wine or have a cup of tea and pull as many pictures as you like but have at least 20.

For now, do not think about your body type, budget, or whether it’s appropriate for your life. You are just getting a sense of what you like.

To get you started, take a peek at my Pinterest Boards. I curated thousands of pins that you can reference and use to build your board.

Challenge #2

Our lives are continually evolving, but our wardrobes tend to stay the same.

If you have changed jobs, got married or divorced, had a baby, had another baby, left the workforce, or are just getting back into it, retired, or any number of lifestyle changes, this exercise will help you get clear on your needs.

Define your Lifestyle

To get a visual of how and where you spend your time, create a Lifestyle Diagram. It’s easy; draw a circle on a piece of paper to use as a pie chart. Now, break down your life according to percentages totaling 100%.

Include work, activities, travel, date nights, anything you spend time doing. It’s essential to see how you are spending your time.

You might find you’re buying a lot for work but have nothing to wear to your kid’s soccer game. When I first did this exercise, I didn’t have enough options for social outings and date nights.

Tip!: We have had some participants take this very seriously! They went so far as to create an Excel spreadsheet and pie chart to capture their percentages. Do what works for you! Of course, a spreadsheet makes my Type-A heart happy.

Here’s a sample:

Again, post your charts in our Facebook group for everyone to see! It’s always fun to see the categories we forget about.
Complete both of these challenges before you start the next round of challenges.

I’m looking forward to connecting with all of you and walking through this process together!


Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

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. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.



The Well Dressed Life Wardrobe Challenge 2020: Week 4

4 Weeks to a Better Wardrobe - Part 4 - The Well Dressed Life
Four Weeks to a Better Wardrobe - Week 4 - The Well Dressed Life

Happy Friday, Ladies!

Today we wrap up our last set of challenges. We’ll focus on discovering new outfit combinations you already own, making sure you have what you need for all aspects of your busy life, and creating a strategy for going forward.

But before we jump in, I have to thank everyone for participating with such enthusiasm!

It has been so fun to see everyone’s closet “after” pictures. This round especially showed us so many examples of how to get creative with organizing a closet. It’s beneficial to see regular closets instead of the unrealistic ones we see on Instagram and Pinterest.

One of the things that set this site apart from others is that our readership genuinely fuels it. I never wanted to start a blog to talk about myself (you would be so bored). So while I certainly feel a connection with our audience, even friendship in many cases, I want this to be a resource first and foremost. The content produced here is inspired explicitly by your comments, questions, and requests.

This week is going to wrap up the challenge, but not the process. 

Remember, it takes time to put all this into practice. That’s why so many women do this challenge every season. 

Now that you know what you need, it’s time to do the work not only to find those items, but figure out how to translate all those gorgeous inspiration pictures into an outfit that will work with your lifestyle, budget, and body type.

If you are new to our community, I encourage you to ask specific questions, and request posts covering different topics. Our readers influence every post on this site. I consider our readers more like clients, so the recommendations, tips, and advice I share are all deeply considered based on everything I know about you.

Use our archives while searching for inspiration. Almost every style post notes how to translate each look based on size and body type.

I guarantee the more you participate in our community, the more you’ll get out of it.

And I’ll be here to help! 

Starting with a LIVE Q&A in our Facebook Group – Details Below! 


Week 4: Create New Outfits and Write Your Wish List

If you haven’t completed week 3, please do that first. If you are just starting, or feel like you’re running behind, do not stress. This is suppose to be fun!

Take your time! There is no rush. These posts will remain on the site for you to reference. If you use Pinterest, you can pin these to a board for easy access.

Challenge #1: Create New Outfits

Spend some time in your clean and organized closet.

Doesn’t it feel so good?

With the clutter removed you might be amazed at the outfit combinations you never noticed. Every time I go through this process I always find a new way to wear something or rediscover an old favorite.

And there is just something so motivating about a clean, tidy closet. 

My closet – after the edit.

To guide you, use your curated Pinterest boards and your lifestyle diagram. Try to recreate a few of the looks for each of your categories. 

Use Pinterest as a search engine. Say you have a pair of black jeans. Type “black jean outfits” into Pinterest and be amazed at how many ideas you get.

Yes, I know the pictures on Pinterest are almost entirely of young, super-thin, super-tall women in four-inch heels

The idea is not to replicate each look. Instead, be inspired by them. Look at the color combinations, pattern pairings, layers, and accessories. Those are the essential elements. 

You may want to swap out a skinny jean for a straight leg or wear a different shoe. We all have to make adjustments to meet our specific needs. 

Here’s an outfit I “found” after I did this challenge in January right before the world shut down.  



View this post on Instagram


🎉How many unknown outfits are hanging in your closet?? . 🥂For date night I gave myself 2 challenges: . 1. Find an outfit I didn’t know I had, . 2. No jeans! . 🤚🏼So many of us go to jeans all the time. . I know I do because my life is super casual and jeans just fit me better. . I’m THRILLED with this outfit. . I had both pieces in my closet and never thought to put them together – and this is what I do for a living! . It shows how important it is to have an organized closet (you have to see your stuff!) and you have to give yourself a minute to look through what you have. . I love a monochromatic moment that combines various textures like the knobbiness of the sweater and the shine of the silk skirt💕 . And, this outfit was so affordable. The sweater was under $30 and the skirt was on clearance for $20. . So carve out some time and see if you can find the hidden looks in your wardrobe! . Swipe to see tagged retailers in picture. . 👼Photo-bomber just turned 14 months and is fresh out of the bath💕

A post shared by The Well Dressed Life (@thewelldressedlife) on

Remember to use your entire wardrobe. Break up “sets,” and incorporate pieces you are saving for a schedule special occasion.

Pro Tip! Take pictures of your outfit options and keep them on your phone so they are at your fingertips when you need a reminder.

Challenge #2: Write Your Shopping List 

As you work through your wardrobe, creating new looks, jot down what you need to create more outfits.

Could you use a different style pant?

Maybe an updated shoe would pull several outfits together.

You might need something as simple as a cami so you can start to wear a lightweight sweater.

Write down anything that would add more life to your existing wardrobe.

Keep this list with you (I keep mine on my phone) and only purchase from the list! By doing so you will stay focused, and your wardrobe will become more functional. If you buy things that are not on the list, you’ll end up with a closet full of items you don’t need all over again.

AND share your shopping list in our FB Group. I use all of the conversations on that feed to help create posts for each season.

Enjoy your new space and the fresh start!

Your closet won’t always look this great. Life will get busy, and you’ll need to regroup. The good news is it will be so much easier to keep it tidy now that you have a system. I follow this process twice a year,  only it doesn’t take four weeks; it takes about an hour to get back on track.

Remember that your wardrobe is ever evolving.

You’ll never be “done.” There will always be something on your shopping list, an item that needs to be replaced or a new look you want to try. I hope that after this exercise, you start to hold your purchases to a higher standard and realize you don’t need so much, you just need the right options for you.

Join me in our Private Facebook Group for a LIVE Q&A!

On Sunday, October 18th at 7pm EST, I’ll host a Facebook LIVE, answering all of your questions, sharing tips, and my best advice to keep your closet organized, and begin to build a wardrobe you truly love. 

To Join our Facebook Private group simple follow this link. Be sure to answer all three membership questions. 





The Well Dressed Life Wardrobe Challenge 2020: Week 3

Four Weeks to a Better Wardrobe - Week 3 - The Well Dressed Life4 Weeks to a Better Wardrobe: Step 3

This week’s challenge is all about getting your space organized! I am a big believer in organization. It makes life easier, saves money, and allows you to manage your time and energy better.

I worked with private clients for over a decade. One thing I know for sure is a messy, unorganized closet space is one of the biggest reasons why women feel overwhelmed (or underwhelmed) by their wardrobes. The good news is it’s one of the easiest issues to fix.

Week 3: Getting Organized

Your closet space should be lovely or, at the very least, tidy. It should bring a sense of calm, not craziness. It doesn’t matter what kind of closet you have. You could have a huge, custom walk-in or a simple bar and shelf. Either way, your experience can be blissful.

Challenge #1: Finish your edit

Last week, we challenged you to perform a QUICK edit. This is my clever way of easing you into a more in-depth edit, especially if you have a hard time letting go of things or just have a lot of stuff. 

If you still have an undecided pile, now is the time to be ruthless. Get rid of anything you don’t love or need. Be honest with yourself.

Are you really going to wear it?

The only exception is if you NEED to wear the piece until you replace it with a better version. Make a note of it. You’ll need it next week when we create a shopping list.

If you are on a weight loss journey, and you have some pieces that don’t fit well, you can keep them, but remove them from your closet and store them someplace else.

I don’t want you waking up to a closet full of clothes that don’t fit. It’s not a great way to start your day.

Be sure the items you decide to keep are modern, fit your style, and are things that you look forward to wearing when you hit your goals.

If a piece is sentimental, give it the respect it deserves. Have it professionally cleaned, remove it from the plastic dry cleaning bag, wrap it in acid-free tissue, and store it with the rest of your keepsakes. 

I love these cedar trunks.  I have one for each of my girls and myself and store special pieces that are either memories, or garments I want my kids to have when they get older.

Challenge #2: Improve Organization

Take some time to find a place for everything. I know, I know; this was supposed to be fun!

I promise that an organized and clean space will help with your creativity. The process of creating outfits will not seem so daunting when you see what you have. A few quick tips:

Remove everything from your closet.

Give it a quick clean. I have seen enough closets in my day to know you have pieces hidden in the back, covered in dust. Dust will destroy your clothes. Take 15 minutes to wipe off your shelves, vacuum, throw away old hangers, and miscellaneous items.

Only put back your wardrobe.

I once found a toaster in a client’s closet that she’d forgotten she’d bought. Find another place for everything else (if you can). Remember to keep your Pinterest board close by so that you can continue to use it as a guide for what to keep and what to get rid of.

Upgrade your hangers.

We love these flocked hangers, which are available on Amazon. I use them all over my house.

Look at what you have before you buy any organization tools. 

Before you run to The Container Store, see what you have laying around your house. It’s helpful, as you go through the items you plan on keeping, to put them into piles to see how many you have.  Have a pile of handbags, belts, sweaters, etc.  Then, reuse and repurpose bins, hooks, and baskets to help store them.

This time around,  I did end up at The Container Store and found some fantastic items that made big difference in my space. But I was super specific about exactly what I needed and didn’t waste money on unnecessary gadgets. 

A Peek at My Closet


You can see the full “transformation” from overwhelmed closet after the holidays, to the tidy space it is now on my Instagram Stories here. You’ll see that I don’t have a fancy, custom space, but it’s clean, organized, and functional. 

And stay tuned for a formal closet “tour” post next week!

Need to catch up on previous challenges? 

You can view Week One, and Week Two here.

Are you following along in our private Facebook Group?  If so, post some pictures of your space once you get it organized and share the inspiration!

Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist View Post 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. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please consider following on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

VIDEO: Peek Inside My Closet


For about two years, our marketing and social media team have been telling me to shoot videos and for about two years I ignored them. Why in the world would I do that?  The world of online “experts” is bursting at the seams. Everyone but me wants to be a YouTube star. The digital world has a dark side, and frankly, I don’t have the best personality for dealing with online bullies and general crazy people.  After meeting face to face with our team last month, I was officially talked into it. To start the series, we thought we would make a few Q&A Tuesday posts into video. These videos will be just like the posts, fueled by either the questions you post in the comments, via email or the questions we get in programs and workshops across the country. The point is to give as many tips and advice as we can, all generated by our community.

A big thank you to my main girl and social media manager Misty, for all the work you put into editing this and to my husband who has the great pleasure of filming these with me.