Well, we made it. Unfortunately, the turn of a new year doesn’t magically make everything better but it does make us more hopeful, like a fresh start or a new page. 2021 feels especially hopeful after the year we just lived through. I have created my vision board, I am journaling daily, set my goals, and created my word of 2021, which you can read more about here. I am ready.

To make things that we want happen, jumping in blindly with both feet is not the way to do it. Yes, it feels good at the moment when you put your stake in the ground and declare change, but actions like this are empty if they are not backed up with a plan. Remember that episode of The Office when Michael Scott declared bankruptcy by standing in the middle of the office and literally declaring it? It’s sort of like that.


A Failure of Plan is a Plan to Fail

I have some big juicy goals for 2021 and my biggest goal is to make sure I support myself in achieving them. Yes, putting in the work and setting up a structure does take away that zingy exciting feeling you get in the moment that you decide you want to make such-and-such change, however, being reasonable and doing the less glitzy work isn’t nearly as disappointing as setting an intention and watching it die on the vine by March. Also keep in mind, nothing meaningful happens overnight and its in the journey itself where we change, not the achievement of the actual goal.

Let’s use the example of losing weight, something that I, and I am sure many of you, have set as a goal for this year. Losing weight the right way, not the cabbage soup/ hope for a stomach virus way, isn’t easy and it’s hardly fun. It requires a sticktoitiveness that and an insane amount of structure, change on your part, the understanding of your triggers, setting realistic actionable steps, the willingness to be humble and a longterm plan that is sustainable.

I read something really wise recently: when there’s a big gap between where you are and where you want to be, you feel overwhelmed (and restless). Setting realistic goals is a great way to help you feel more confident.


So let’s talk about your style, the reason why you are here. If you have a goal for a better style in 2021, here are three things you can do to ensure your style is off to a good start.

#1- Make Your Goals Clear

January 1 rolls around and, with a style goal in mind, the first thing most women do is jump into the closet to purge and organize. To which I say, lady, you’ve got a lot of work to do before you even think about that step. Doing this is like setting sail on a boat with the hope of winding up where you want to go. You have no course charted, you don’t even have a compass.

So, where are we going? What do you want the end result to look like? You can consider writing a vision statement for your style that includes feeling words like, when I get dressed I want to feel <blank> in what I wear. You can start an inspiration board on Pinterest or even a vision board that you keep in regular view to remind you where you plan to set sail. You can do both. When setting a new goal, I usually write things down and create a visual presentation like a vision board.

At this point, we’re not even looking at what isn’t working with your wardrobe, mistakes you may have made or money you have probably wasted in the past. All I asked you to do is figure out where you want to go. Besides, if you knew how to get there you’d be there already. This is your opportunity to be dreamy and to get excited before the real work begins, so don’t squander it.

Ask yourself, will you commit to setting a style goal for yourself that you can reference regularly? What will you create? How will you keep it present in your life?

#2- Take an Inventory…of Your Life, not Your Wardrobe

It’s time to get a little uncomfortable because this is where you start taking a hard look at yourself..hair shirt or self-flagellation not required. In fact, I highly encourage you to give up the guilt or shame because it’s useless and keeps you paralyzed. You didn’t shoot your neighbor’s dog, your wardrobe and style went awry. It’s not the end of the world.

In addition to looking at mistakes, taking an inventory of yourself also helps with understanding how you operate. Let’s call it your style-style (I just made that up.)

The thing that bothers me most about fashion advice is it always packaged in this one-size-fits-all way, similar to that bunk that gets spewed about everyone needing to own this or that item. Lies, I tell you. All of it. It’s quite probable that you have gotten your wardrobe off track just by trying to follow some fashion advice you have gotten that just doesn’t work for you.

So let’s start by taking an inventory of what you feel are your biggest struggles with your style. Again, you don’t have to know how to fix the problem. At this point, we are just identifying what the problems are.

First we’ll look at your struggles you are dealing with when it comes to wearing clothing. Some examples could be:

  • I don’t know how to dress this part of my body
  • I wear the wrong colors, but I’m not even sure
  • I didn’t like the way I look in my clothes
  • I didn’t feel like myself in what I wear
  • I don’t know how to put an outfit together
  • I have gained a lot of weight and my clothes no longer fit
  • I never look as good as how I picture it in my head

You get the idea. Come up with ten (or at least 5) of yours and prioritize them from 1-10, One being the biggest priority that you want to work on and ten being the least important.

The next step will be learning your style-style, or discovering what your style is in managing your wardrobe. This will be a list of things that you struggle is the first step in figuring this out.

  • I get overwhelmed by too much stuff and too many choices
  • My drawers get messy easily
  • I hate shopping
  • I like nice things but I don’t want to spend the money
  • I never make time to get to the dry cleaner
  • I have too many clothes and nothing to wear
  • I bought things that never got worn

Again, come up with around 5-10 of your own and, like the last list, prioritize them 1-10.

Now what we are going to do is create specific and measurable changes you can for the top 3 three things in each of your lists by creating actions that work for your style style. Here are some examples:

  • Problem: I bought things that never got worn
  • Action: Give the item three more months and if I don’t wear it I will toss it. Before I get rid of it, I will make a list of the reasons I never wore it so I can avoid these problems in the future
  • Problem: I don’t know how to put an outfit together
  • Action: I will forgive myself for not being naturally good at it and will find X amount or resources to help me with this and if I am still struggling, set aside X amount of dollars to get some professional help.
  • Problem: I get overwhelmed with too much stuff and too many choices
  • Action: I will create a small tight wardrobe that mixes and matches well and will create an input/output rule. For every new item, I will get rid of something I own.
  • Problem: My drawers get messy easily
  • Action: I will accept that I will never have drawers that are perfectly neat and will make a plan to organize and refold my clothes in one drawer a week.
  • Problem: I never get to the dry cleaner
  • Action: I will only buy dry clean only clothing for special occasions.
  • Problem: I have gained a lot of weight and my clothes no longer fit
  • Action: I will give myself X amount of months to achieve the weight I need to be to wear these items. If they no longer fit, I will get rid of them.
  • Problem: I wear the wrong colors, but I’m not even sure
  • Action: I will get a color analysis by XX date. If getting color analysis isn’t affordable, I will find XX resources to help me learn how to understand my own color analysis.

You see, what you have identified aren’t always just problems. They can also be indicators of you not being in tune with yours your style-style or how you operate. The goal here is to set yourself up to win by creating SMART goals that work with how you are wired.

SMART goals are:

  • S: Specific
  • M: Measurable
  • A: Attainable
  • R: Relevant
  • T: Timebound

After you have created actions around and mastered your top three from your list, you can move on to your next three, and so on. You can also plan on adding more to your list as you notice more things you would like to work on. Don’t overwhelm yourself, chip off a little at a time and work your wary down your list a few challenges at a time.

Will you commit to taking on this next step? Did I just hear a hell, yea?

#3- Establishing your Baseline (Now we’re talking about your wardrobe)

As I tell clients all the time, I can’t help them achieve where they want to go with their styles until I have a sense of where we are starting. I call this, getting their baseline. This is done after we have established where they want to go (step 1). We do it in this order because how can you know for sure what you should keep and what should go if you don’t know where you want to ultimately wind up? Knowing what you want the end result to be makes it a whole heck of a lot easier to part with something that does not fit into that plan.

If you are looking at some of the images you pulled for your vision board and realize that there is nothing about these looks that fit into the life you live, remember, this isn’t about duplicating something exactly, this is about evoking the feeling you have when you see these amazing outfits or asking yourself, if this woman I am inspired by was living my life what would she wear?

These are the moments when you have to be truthful with yourself and when you have to let go of the things that don’t fit into this granular view of your style. And the more granular you can be the better the results.

Try things on. Do you feel the way you want to when you wear it? What are some of the words you came up to describe how you want to feel when you get dressed? Is there a match?

Lastly, let it go. Just stop with the holding on. Seriously. If something doesn’t work and you are seeing letting it go as money wasted, I implore you to reframe that conversation. How about instead of:

“I never wore this, there are tags still on it. Such wasted money. I should keep it.”

You reframe it to,

“Even though I spent money and never wore this item, it’s not reflective of my style goals and I will let it go. Before I do, I will take a moment to learn where I went wrong so I can avoid making this mistake in the future. I will pass it on to someone else, who really does need it and can enjoy it.”

Remember, I said no self-flagellation or hair shirts!

Can you commit to being gentle and forgiving with yourself as you let go and discover your baseline with the understanding that finding this baseline will help you succeed in developing your own style? Can I get an Amen?

These first three steps are just the beginning but I think it is enough to get you started. In upcoming posts, I will dig deeper into offering you more steps around developing your style and setting goals in a sustainable way.