Wardrobe Upgrade – Why Dress Well?

Happy September, everyone!

This month is going to be all about clothing and wardrobes – the outer image you present to the world.

Some of you are probably already checking out right now.  Please don’t.  The purpose behind the posts this month is not really to tell you how bad your style is, but to help you move forward with choosing things that are going to make you feel more like yourself.

Basically, this month is for the people who always feel weird in their clothes or feel like they aren’t truly representing themselves when they pick out their outfit for the day.

I’m not a fashion guru by any stretch and I’ll be the first to admit that I don’t really understand high fashion.  I don’t get why people would design things that look like clouds or are completely made of straps or whatever.  But I’m not judging, I can appreciate the art, I just don’t understand what to do with it.

No, I’m just a person who realized one morning that the clothes I was picking out of my closet weren’t a representation of the person I really am.  They represented who other people wanted me to be.  I also realized that I was just buying a lot of things because they were cheap or because I randomly liked the pattern or color, not because I had a plan for them.

In the next several weeks I’m going to show you ways to organize your clothes so that you are comfortable, confident and presenting the person you really are (or want to become).  This will probably be more applicable to women by default because I am a woman, but there are definitely some concepts in here for men as well.  I feel that men have this whole clothing thing a lot easier than women because you can just throw on a nice pair of pants, a button up and some shoes other than old tennis shoes and you look great.  Comb your hair a bit, make sure you’re face is washed and then walk right out the door.  I don’t blame society for this because I do enjoy dressing up probably more than the majority of men and there are men out there who enjoy looking fashionable just as much.  It’s just that guys have it a whole lot easier than women somehow.

But anyways.

Let us discuss why it is important to care about your outward appearance.  First off, I want you to get rid of the ideas that a.) you don’t care what you look like and b.) you dress to impress other people.

For some of you, point ‘a’ won’t apply.  I’ve found that the majority of people absolutely do care what they look like, they just aren’t comfortable with their clothing choices and they don’t know how to change so they tell themselves that they don’t care.

And maybe some of you don’t care at all!  But you need to.  Here’s why:

You aren’t dressing for other people, you’re dressing for you.

A very important thing you need to realize in your life is that you can’t go around trying to impress everyone.  Either you will or you won’t but most people you pass on the street aren’t going to think about you beyond those three seconds when you share personal space.  Try this experiment: Have you ever seen someone on a metro or at the mall that you thought “wow! They look nice!”  The answer is probably yes.  Now ask yourself how many times you’ve thought about that person since then.  Probably not a lot.  If that’s what you do, how often do you think other people think about you?

So stop worrying about other people!  And besides, when you dress for yourself in a way that shows your true personality you’ll have more confidence and when you have more confidence, people will be impressed by your attitude anyways.  So it’s a win-win.

So then why wear clothes at all?

Because it is another way to show the world who you are.  You are a human being who has stories, memories, experiences and thoughts that are different from everyone else on the planet.  You also have goals, hopes and a background that no one else has.  None of these things are things to be ashamed of, they make you who you are!  Clothing allows you to demonstrate how you have combined all of these non-tangibles to create your unique personality.

So you don’t dress to impress other people, you dress to show them who you are and if they don’t like that, who cares?  Your goal in life is not to make everyone like you.  Please get rid of that sort of thinking.  It will only exhaust you and make you susceptible to everyone’s emotional whims.

Now, you’re probably wondering how one goes about “dressing for who they are”.  Will it require you to buy all new clothing?  Will you have to throw away everything that you love?  What if you actually do like your clothing?  And how do you figure out who the heck you are anyways?

We’ll talk about all of that in the next couple of weeks.  We’re going to walk through how to figure out what you like and don’t like in your clothing, how to organize your closet so that you are more confident picking out outfits and how to shop effectively to build a cohesive wardrobe that you’ll actually enjoy working with.

I’m not even going to get crazy with you talking about silhouettes and shapes and cuts.  We’re going to talk about colors, fit and quality.  Just practical stuff.  If fashion is the sort of thing that strikes your fancy I’ll include suggested reading and more websites that will take you even further.  But for now, we’ll stick with the basics.

Because revamping a wardrobe will take a lot of introspection and understanding of who you are, I’m going to give some optional homework for this post.  I highly suggest you complete it (it’s fun!) before reading the next post.  Take as much time as you need for this and really consider what you’re doing.


  1. Create a Pinterest board dedicated to clothing and go on a pinning spree where you just pin absolutely any piece of clothing or outfit that interests you.  You can go as crazy as you want during this first step.  Try to get forty to fifty pictures pinned on your board.
  2. Once you have these pictures pinned, go back through your board and consider if you’d really actually wear the items in each picture.  It is fine to like looking at something but if you wouldn’t actually wear it, either move it to a different board or delete it altogether.  Important – there are plenty of people who would definitely wear a fancy outfit with 100 pieces because it’s a fun thing to do.  But you need to consider if the outfits you are looking at would actually fit into your daily life.  I might adore tulle skirts and want one in every color but I know for a fact that I have nowhere to wear them and they would just sit in my closet.  I have a board with some tulle skirts on it.  This board is not the same as my wardrobe board.  My wardrobe board is specifically for clothing that I can actually wear on a daily basis.
  3. Go through the board one more time and remove items that you just aren’t liking as much any more.  Add more things that you’ve found.  Consider Pinterest as a giant, free mall where you can buy and return as many clothes as you’d like.  Add and delete photos until you have a board of about thirty to forty pictures that you really like and that you can honestly see yourself wearing on any given day.  This is going to take awhile and you’ll probably constantly be redoing it all.  You’ll think you have everything perfect and then you’ll see an outfit that you just adore and everything is going to get turned all upside down.  That’s great!!  This process is all about exploration and discovery.
  4. Once you are 100% happy with your board (and you might never be, just get as close as you can), scan through it and look for similarities.  Do you have a lot of tank tops?  Do you see a lot of one particular color?  Do you have more skirts or pants?  Do you have a particular type of jacket that you pinned a lot of?  What sort of shoes did you choose – boots, flats, tennis shoes?  If you chose pants, what sort of pants did you choose?  Were tops fitted or flowy?  What sort of jewelry is most prominent?  Be careful during this step that you don’t try to categorize your board into something like ‘Bohemian’ or ‘beach’ or ‘goth’ or anything.  It’s your board so the category is you.  You will most likely have a mixture of different styles in your board so don’t try to fit yourself into one particular ‘style’.
  5. The similarities you just identified are ingredients to your personal style.  Write them down in your journal so that you can keep track of them.  (We talk about this much more in depth next week so don’t do this if you’re confused.  Just focus on finding similarities.)
  6. During this process you probably also found some things that you don’t like and will never wear.  Write these things down as well.

For reference, here is my Pinterest board if you want to peruse it.  You’ll see a lot of skinny jeans, cardigans, blue/green/cream, boots and cozy sweaters.  I like natural touches like lace, canvas and leather.  My look is simple and organic, polished and comfortable.  I call it “Laura Croft Goes to Whole Foods”.

You probably will have a couple of reiterations of your Pinterest board before you finally settle on something that you can really relate to, and also remember that the people in the Pinterest photos are usually professionally styled using extremely expensive clothes that have been tailored and have hired professional makeup/hair stylists.  If you’re just starting out, don’t get overwhelmed with the process.  Start with whatever you can.

Most importantly, have fun!

One comment

  1. Interesting post. I like to dress how I feel, and don’t really care if people think I look weird. I do like to look at dresses and skirts, but absolutely hate the thought of actually wearing them myself. Prefer trousers and shorts. Interesting idea of yours.


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