The Well Dressed Life Wardrobe Challenge Spring 2019: Week 1

Four Weeks to a Better Wardrobe - Week 1

Ladies, today is the day you start to finally 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 blissfully retired and finally spending some time focusing on your passions, you want to look and feel great during whatever your season of life.

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

So, who am I?

As many of you know, I was a personal 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 over a decade I moved on to focus on building our online business. But the experience of working with thousands of clients, all hard working, down to earth women, continues to influence our fashion and style posts today.

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

I also pull a lot of perspective from my 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 a thing of the past.

But I also know how important taking care of myself truly is, how sometimes just putting on a pretty outfit, or painting your nails can make a crummy day a little better, and that I navigate life happier and more confident, when I look and feel my best.

But It’s About You

Every woman wants to look stylish and feel beautiful. But not everyone is able to 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. My goal when this challenge is over is that you will have a clear understanding of what you like and what will work for you so shopping is easier.

Here’s How the Wardrobe Challenge Works:

Every Friday afternoon for the next four weeks (starting today) we will share a series of challenges to help you build a better wardrobe. Take your time with each challenge. It’s great if you can get them done in a week’s time, so you keep momentum, but if you can’t don’t worry. 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. 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.

Let’s get started!

Picture of Laptop showing Pinterest Boards

Week 1: Finding Inspiration and Your Personal Style

Challenge #1

Pull Inspiration Pictures

In the early years of Kristel Closets, I would arrive at an initial appointment, which always took place in our client’s closet, and she would have trouble describing her style. It didn’t take long for me to realize that having a visual helps you to see the common elements in styles you like even if you don’t have a trained eye.

So I created a series of pre-work for them to complete prior to our first appointment. It was designed to help the process move smoothly and efficiently. I was always aware of the investment our private clients made 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 that we spoke the same language.

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

Many of you are looking to streamline and simplify your wardrobe others mentioned that they recognize good style but have difficulty translating for themselves.  Without a clear understanding of your style, it will be a challenge to edit your wardrobe properly.

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

Picture of Laptop showing Wardrobe options on Pinterest Boards

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. Feel free to share your boards in our Facebook group. It’s fun to see everyone’s boards and sharing gives inspiration to others.

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 own board.

Challenge #2

Define your Lifestyle

Our lives are constantly 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.

To get a visual of how and where you spend your time, create a Lifestyle Diagram. It’s easy; just 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 important to see how you are spending your time. What you might find is that you’re buying a lot for work, but have nothing to wear to your kid’s soccer game. When I first did this exercise, it was evident 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.

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!



Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

  1. At 69 3/4, in May I’ll be 70….I still dress young/appropriately, have been retired for a very long time, have grandchildren, 12, 11 and 10….very active…..volunteer…..and I still from time to time get in a quandary as to what to keep and what to purge. I just went through my closet again, as I do quarterly, and purged a ton of things……I’m finding getting dressed to be so much easier…..I’m going to go through my jewelry next….I find myself wearing the same pieces…..I’m looking forward to following your exploration on the wardrobe. I can always learn something new…..I enjoy your blog….

    1. Hey Jill! I’m always so happy to hear from readers and learning that our content appeals to women of all ages in all chapters of life. Since you seem to be already organized and comfortable with letting items go, pay close attention to this first challenge. The process of collecting inspiration pictures can be really eye opening. 🙂

  2. I have done your Style Challenge twice and loved it (and both times felt inadequate that I couldn’t do the weekly activities and would get a little overwhelmed with a busy travel life and schedule, I LOVE the 4 weeks to a better wardrobe context and takes the pressure off those of us crazies who like to meet deadlines for accountability. I am rarely on Pinterest anymore but do love my boards, my style is still ridiculous shoes with everything 🙂 – a great outcome of this challenge was donating so many of my unused, barely worn clothes to others who can enjoy them. Thanks for all you do and this new look and feel of the site and blog is awesome! Mint green suits you.

  3. Thanks for doing what you do!! Happy to try this 4 weeks challenge! (Who doesn’t like a good challenge to start the year?) Once we have a nice big board of styles we like, are we supposed to know how to edit and shop? I am good at pinning but not at then determining how that should inform my decisions!

    1. Hey Christie, We’ll get to that in the next few challenges. The first thing to do is pin all the things you love and complete the lifestyle diagram without thinking about how to edit or shop just yet;)

  4. OK I am playing catch-up a bit. Here is my board:
    No surprise here, but a lot of my pins are from this site!

    In lieu of a pie chart, here’s my breakdown:

    20% of my week working in a creative office
    10% of my week working from home
    14% of my week lounging at home, playing with my daughter at home
    40% sleeping (I love my sleep)
    4% dates/going out with friends
    9% Running errands or casual weekend activities with my family
    3% gym

  5. I work at home half the time in old, stained sweatpants and an REI pullover from 2002, and in an office half the time, trying to fit in with consultants who dress pretty formally, in expensive, fashion-forward clothes. Most of them do not have children and shop or get manicures for fun. When I’m not working, I like to exercise and spend time on the floor with my 3 young kids. So breakdown: 50% casual, 30% professional, 20% athletic. I enjoy expressing my creativity through my clothes, but right now, I don’t have time for it. Maybe a more edited wardrobe would help me dress faster and feel more pride in what I’m wearing. Here’s my board. I dutifully deleted items that didn’t feel special to my style, so now, everything here I really like.

  6. Dear Megan, I am 74 years old and fully retired, when I worked for a corporation I had no problem knowing what to wear, now I find myself being rather sloppy!
    I started a capsule wardrobe and purged my closet big time, and it not very interesting. I purposely have not gone out to buy anything new until know my style and I know where to start. I have used Pinterest and I am now finally seeing a pattern, I’m thinking that I am a classic casual. I am very excited about going through your challenges. Thank you so much!

  7. Hi Megan love your site, my problem is I have a wardrobe full of outfits for evening outs ( not Posh )
    holidays in France (not summer September time ) dresses expensive Jeans and Expensive knitwear for weekends away.
    And not enough everyday suff. I am retired 64 but occasionally work in our own buissness look after Grandkids ,shop meet friends for Coffee and have dressy/casual nights out for meals,

    I havent a clue where to start please help what should I keep in my best /going out wardrobe/holiday wardrobe, and my
    everyday wardrobe.

    Best regards Jackie

  8. Good Morning – love your website Meg and thanks so much for putting together this challenge. It’s my first and I was excited to do the weekly graph and Pinterest board. For no particular reason I’d been working on a Style Pinterest board and so glad it now has a purpose! I don’t know how to attach it here to share but upon review it has a clear theme; minimalist, monochromatic, neutral colors, pointy toe heels/ flats. This was especially interesting to me because I have tons of scarves that I never wear.

    I spent decades in the corporate world and based on the volume in my closet, my head must think I’m still there. But I’m not. For the last 8 years I’ve worked from home and see clients in my home office. I could wear the exact same thing everyday and no one would know the difference. Several times a year I attend corporate business meetings which are trending to a more business casual vibe. My graph is below. This exercise really helped me focus on what I do and where. Thanks so much Meg!
    80% home office
    10% professional meetings
    5% dress up – symphony, cocktail parties, special dinners
    5% casual weekend

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

  • 🌞Hello Summer.
🌈Today on The Ten List:
🏖Why I prefer summer to fall
🍹Drink snobs are coming for the Aperol Spritz
📚A book for quiet introverts like me
🎉Inexpensive summer dresses for your next casual party 
And more today on the blog
link in profile☝🏼

Follow Me!


Let's stay in touch! Enter your email to sign up for our newsletter and to get your free copy of our wardrobe checklist

© 2018 Kristel Closets, Inc.

Privacy Policy

We use affiliate links throughout this site. This means that when you click and/or buy a product we recommend, we receive a small commission. That in no way affects our opinion of those products, and we only link to products we personally recommend. Please read our full disclosure policy.