The Well Dressed Life Wardrobe Challenge 2020: Week 2

4 Weeks to a Better Wardrobe - The Well Dressed Life
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.  
Today, at 2pm EST, I’m hosting a Facebook LIVE in the group to answer any questions you might have and get us set up for this weeks challenge!
There have already been some big take aways 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 the comments in our group. 

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 our own unique combination of everything. 

For example, I use to think I was “preppy”. But I’m not, at all. 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 have a deep aversion to 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.

So to help you with this, go through you 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 mixes and matches and you always look 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 skirts.
  • Does your board have scarves and accessory heavy looks, but you never incorporate them into your daily outfits?

These are the kind of revelations you might have when you finish this exercise – and it’s fantastic.

Challenge #2:  A Quick Closet Edit

How to Finally Let Go of Clothes You Don't NeedYou can do this next step all at once or over a few days, it just depends on the volume 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 we 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 don’t like a lot of patterns and I wasn’t wearing them.

So why do I keep buying them? In my case, I thought I needed variety. I was also using Stitch Fix at the time, and kept a lot of 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 time we offer it. 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,” put 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 ok 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 is reflective of 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.

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.

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

How To Find Your Style

Finding your Personal Style

Today we’re talking about how to find your style. 

Discovering your personal style seems easy enough, but start to dive into it and you’ll quickly realize it can be confusing and a little overwhelming.

Have you ever sat down and thought about what kind of clothes and looks you like?

Probably not, because as busy women… who has the time?

For many, myself included, there comes a point in life when we end up with less of a style and more a closet full of clothes we accumulated over the years. 

How to Find Your Style 

How to Find Your Style

The decades since I graduated from college are a hodgepodge of personal style trial and error.

I fully embraced late nineties style with my low rise jeans and mid drift tops, not so much a style as it was  required uniform for frat parties and college life. 

After graduating I remember so clearly trying to look like a “grown-up” or what I thought I grown up looked like. Thankfully, that was a quick phase and I spent most of my twenties and early thirties experimenting with different styles, all while having babies,  and building a business.

While I’ve always understood the fundamentals of dressing, like proportion and fit, it’s very different to navigate personally. As we age and watch our bodies change, it took me a minute to understand that what worked in my 20’s and 30’s doesn’t work on my body at 40 after three pregnancies – no matter how much I work out.

At my core, regardless of my age or size, I’ve always loved classic American Style. As a young girl, I worshiped Oscar de la Renta and Carolina Herrara. I was mesmerized by their shows, models, and dreamed of growing up to exude their effortless elegance.

But it wasn’t until my late 30s and now at 40 when I felt like who I am as a woman and my personal style match. Like they are finally meeting at the same point. 

Because for years, I convinced myself that that was too boring. So I bought things because:

  • I thought I should like it.
  • It was on sale.
  • I was just happy it fit.
  • Or all of the above.

Maybe that’s the beauty of aging, the confidence you get in being able to say, this is who I am

How to Find Your Style

So how do you create a style that feels authentic?

What are you supposed to do when you like everything?

And where should you start if you have no idea?

Today, we’ll talk about how you can find your personal style, based on what worked for me, and the strategies we used to help clients over the years.

How to Find Your Style in 6 Easy Steps 

How to Find Your Style

How to Find Your Style in 6 Easy Steps

When I worked with clients, the first step in our process was to figure out her style. 

I created a client questionnaire, which included a section that asked them to think about women with a style they admire. It could be anyone, but it always ended up being celebrities from Jackie Kennedy and Grace Kelly, Laura Hutton, or more current famous women like Jen Anniston or fictional characters such as Olivia Pope. 

It was an easy first step to get a sense of what the client liked.

To start this process, ask yourself, who do I think always looks great?

This is like a brain dump; it can be anyone with any style. THEN, take that list and narrow it down to who you want to dress like. 

For example. I love Diane Keaton and Helena Bonham Carter. I so appreciate their bold, wild, and unique style. But do I want to dress like them? No. 

Readers often tell me they get stuck here because they like everything. And I get that!

It’s a lot like when you’re in the process of decorating your home. You can enjoy all kinds of style, but what do you want to live in? 

Can you want to live in more than one? Sure!

And that’s what makes your style unique. It’s how you combine those elements in your own unique way. 

I narrowed my list down to three:

  • Gwyneth Paltrow
  • Oliva Palermo 
  • Carolina Herrera

What do they have in common? They all share a classic American style with some modern elements that feel relaxed and casual.

Who’s on your list?

create a visual

Of course, we don’t have the resources (budget, stylist, make up artist, etc.) to dress like a celebrity every day. So we want to create a visual to help guide us in a practical way. 

This step is by far my best, most well received tip. We go through this process in detail in our free Wardrobe Challenge (coming back in September!).

It’s the most effective way to break down the difference between styles you like and styles you want to live in, AND it helps you build a wardrobe you love quickly and easily. 

Spend some time on Pinterest. Create a personal style board, and “pin” all the looks you like. Then, and this is important, go through them and edit down to only the ones you love.

You may have pinned all different styles.  But remember, there is a difference between having an appreciation of a style and wanting to live in it.  The pins you keep should only be the ones you want to live in.

After you gather a few dozen pictures look for cohesive elements. 

Do you prefer:

  • Pants or skirts?
  • Silver or gold?
  • Mixing prints and patterns or monochromatic?
  • Romantic or tailored pieces?
  • What colors show up over and again?

You’ll quickly discover there is a thread of commonality within the looks you keep. 

Having clarity around your preferences is the first step in understanding your style and making better choices going forward.

Once you’re board is together, use it as a guide while shopping. Before you make a purchase, ask yourself if that piece will help you create the look you are going for. 


Armed with your Pinterest board, do a quick edit purging everything in your current wardrobe that doesn’t get you to your ultimate style goal.

Quite literally, stand in your closet with your Pinterest board open and see if your current wardrobe is a reflection of it.

Don’t be discouraged if it doesn’t. That’s generally the takeaway.

Follow our tips on how to organize your closet in 60 minutes.

Be ruthless. You’ll feel lighter when you get rid of items you don’t like, need, or use.

Pick a Few Signature Pieces

As you look at your favorite styles, look for what pieces keep showing up.

For me, my signature pieces ended up being dark skinny jeans, an animal print flat or bag, a crisp button-down, white tee shirts, a tan boot, and better jewelry and for work, sleek dresses and neutral-to-me pumps.

These pieces work as an anchor for your style. They are the items you can always count on to ensure your outfit “looks like you.”

Follow the Rule of Three

One of the reasons our wardrobes and style goes off the rails is because we don’t put the proper time and strategy into shopping. We need to be intentional about what we bring into our closet. 

As simple tip to follow when building your wardrobe is to only buy something you can wear three different ways.

The pieces that meet this criterion are what should be your core wardrobe pieces. These will help define your personal style and make it easier to get dressed.

Of course, you’ll buy items that you can’t wear three ways, but they should be few and far between. 

Trust your Instincts

As you move through the process of discovering your style, you’ll start to feel more confident in your choices.  It’s important to trust your instincts.

Don’t talk yourself into a purchase you’re not thrilled to make.

Stop wear something because someone told you to.

Avoid buying something just because it’s on sale.

The process of building a wardrobe takes time. Try not to feel overwhelmed by everything you might need.  Write a list of what you could use to pull some outfits together, and only purchase from that list.

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 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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