I went on a 60 day dressing well challenge to see if changing what I wear could change my life. The answer shocked me to the core.

How would you define a fashion victim?

A fashion victim is somebody who loves fashion. Follows all the latest trends. Wishes they could be a style icon. And yet despite their best efforts fashion betrays them in the cruelest way. Their overzealousness makes them look ridicules. The harder they try the worse it gets.

To love fashion is to be in a relationship with a lover who plays head games with you. “Come heather! No go away! I want to be loved. You are smothering me.” It can feel like there is no making peace with fashion.

To truly look stylish you have to look like you made no effort. As if it happened naturally. Certain people have this magical cone surrounding them all the time. They are never caught off guard because they always look good. It can seem that they get out of bed and a style fairy waves her magical wand to transform them into fashion titans ready to sit on a pedestal to be admired by the masses.

O! How I yearn to be one of those people? Actually, I don’t. I don’t aspire to become a fashion icon. I would much rather be known as the person who wrote brilliant novels instead. However, I do wish I could dip a timid toe into the ocean of stylishness and not feel like a giant shark will swallow me whole each time I try. What I really want. Is to make peace with this one area of my life. Either not care about fashion and be ok with the outcome of that choice. Or do care about fashion and find a way to make it work without constant drama. Is that too much to ask for? How hard is dressing well on a daily basis?

And yet, if you make no effort whatsoever, then you look disheveled. Trust me. I have a bit of expertise in the area of looking shabby. I can start a 9 part online course of the fine art of looking dilapidated. I have perfected the art of it.

I have a closet full of evening dresses, sequin pieces and dreamy fabrics. And yet most of the time you will find me in sweat pants and a sweat shirt. I have a serious case of fashion psychosis. On one hand, I am shopping for a fantasy life where I am a princess in a fairy tale. The only missing piece is a tiara. In that alter reality I am constantly stepping out to attend glamorous cocktail parties. In another dimension, some define as real life, I have the existence of a boring mom with no taste, no imagination and no time to fluff about with silly stuff like outer appearance. I look like a woman who had given up on herself. Let things slide. Given up hope. Can you hear the piano playing the moonlight sonata? No! here it is on Spotify.

Please play it while reading the rest of this blog post. It will enhance the reading experience. I promise.

To remedy my bi-polar fashion problem, I decided to spend 60 days dressing well everyday to see what would happen. My 60 day makeup challenge encouraged me to tackle something harder. “Who knows? Perhaps this fashion victim can turn into a stylish lady.” I thought to myself. The rules I set for myself were simple:

The rules of the dressing well challenge

1. Make an effort to dress stylishly every single morning even on days when I was staying home.
2. My goal is to look put together, nothing more. No need to be glamourous or formal.
3. Find a way to have fun during the 60 day challenge.
4. The clothes had to be functional and comfortable because I would spend most of the day wearing them.
5. Sweat pants and sweat shirts were out. Any clothing article that has the word sweat associated with it was on the black list of forbidden clothing list.
6. Observe and record what I felt. Everyday record whatever came up in a journal.

I had no idea of what I would discover at the end of the exercise, but my 60 day makeup challenge gave me encouragement that fixating on the superficial can yield deep insights into my psyche.

What happened next surprised me to the core. I was blindsided. Keep on reading.

The timeline of my fashion challenge:

Example outfit

Here are some of the outfits I came up with.

I am not going to list all 60 of the outfits because that would be tedious. Here is a sample of three to give you a general idea.

Jeans shirt blazer

Denim pants, white cotton shirt and a blazer on top is a fantastic combination of casual and formal. I wore this combination of things on repeat during the 60 day challenge.

Skirt and a blouse

An easy combination to put together if you have a basic white blouse and a basic black blouse in your wardrobe. You can pair them with almost any bottom and tada! ….. you are dressing well and you didn’t even know it.

Dress

Wearing a dress with a denim jacket on top became a favorite. I paired this denim jacket with multitudes of dresses. I felt lady like without feeling overly stuffy.

As you can see none of these outfits are exceptional or brilliant. But they did require a tiny bit of an effort to put together. Like I had to spend 5 minutes thinking about it in the morning.

Style Gurus

I began to follow styling gurus for tips to remedy my unstylish self. My favorites are in no particular order.

Busbee Style

Busbee style is geared towards women over 40. I enjoy all the practical down to earth style tips provided on that channel. She loves drama in her clothes but not her life. Although many of her styling tips are down to earth, there is a dramatic flair included through out. Totally appeals to my sensibility.

Christie Ressel

Christie Ressel is super fun to watch. She has a knack for combining colorful fun elements together. Watching her videos is just a joy. I always love it when she finds creative ways of putting evening items in everyday wear. If you need encouragement to wear sequins just to go the supermarket, this the stylist for you. When it comes to creativity, this fine lady gets an A+.

Kim XO

Kim XO has more of an edgy style. Less lady like and more grunge. Perfect for when you want to look casual but you still want to make a statement.

From all three I learned important and interesting things:

I learned to pay attention on basics. I made sure to have stable clothing articles such as a basic white t-shirt and a basic black t-shirt that allowed me to mix and match with different bottoms.

I learned to make several outfits from the same clothing article. For example, to use layering to morph a dress into a skirt. That way I extend the usage of the clothing articles in my closet. My favorite trick I learned is to take a special occasion dress and turn it into an everyday dress by adding a shirt or button cardigan on top. To bring some of that fantasy life into my daily life. Yes! even sequin numbers were invited to play in my challenge.

I learned interesting color combinations. Which colors go with which. When in doubt I matched everything with either white, black or beige. That kept it safe for me.

I learned to use simple accessories to style up. A basic belt, a dainty necklace and a touch of lipstick applied with care can make a difference to the overall look.

Owning expensive clothes doesn’t matter. The most important factor is putting a bit of attention and thought to the details.

Organize my closet

Around day 30, I realized that my wardrobe is in disarray. Ok I always knew that my wardrobe was in disarray.  What changed is that it started to bother me. I didn’t know what clothing I actually owned. The things I did know that I owned I didn’t know in which pile to go fishing for it. Do you feel my pain? I felt a sudden urge to get my closet organized. Although, this wasn’t part of the original plan, I went for it. I felt leery about straying from the original challenge rules. You have no idea what a difficult task this is for me. My closet has always been a shrine to mess. Like I am a messy person and I am proud of it. My closet was a demonstration of my individuality. It felt as if I was slicing off a pound of flesh to get it done. When I told my husband I planned to organize my closet he laughed and said: “That is impossible. You will organize it and it will get messy again in a few weeks.” Despite whatever psychological barrier that has prevented me from getting it done in the past. I did get it done. I divided the task into sections:

1. Tops
2. Bottoms: Skirts, trousers
3. Dresses
4. Sleepwear and loungewear
5. Undergarments
6. Jewelry and accessories

I worked on organizing just one elements of my closet per day. That way it didn’t feel crazy overwhelming.

 Suddenly, I realized how much clothes I actually have. For example, I came face to face with the realization that I have a red dress obsession. I had no idea this was the case.

My red dress obsession

I have 5 red dresses. Two from the same store. For some reason I am naturally attracted to that color when going shopping. What was I thinking? I immediately issued a red dress moratorium on myself. I still catch myself ogling red dresses in the shopping mall. But then I remember that I have too many already and stop myself in my tracks before I have a chance to whip out my credit card.

Duplicate clothing

In addition to the red dress problem, I discovered many items that I have duplicates of or near duplicates of. Things that are similar to each other.

Beautiful clothing

The final thing that I discovered after my closet revamp is how much beautiful clothes I already have. Over the years I have accumulated a nice stash of fantastic pieces that I rarely wear. I developed the determination to make the best of what I own. I constantly found myself saying to myself: “I have this? why don’t I wear it?”

Joy descends from the sky

Once I got my closet organized, I felt a deep sense of joy descend on me. A feeling of satisfaction. As if a silky gossamer blanket had descended on me from the sky to envelope with a sparkly sensation. The thought that popped in my mind was: “I always wanted to be a stylish lady and here I am, I have all these beautiful clothes.” Just looking into the closet in my bedroom became a joy. The old Sufi story of the beggar who discovers that he is sitting on a box full of gold kept coming up for me.

Thinking about what I feel like wearing in the morning is a pleasure not a chore. I started to look forwards to getting dressed in the morning.

I plugged on.

You might be thinking: “Yay! Happy ending! Let’s wrap up this blog post. You would be missing the grand finale. The same way the first movement on the Moonlight Sonata is all sad and slow. As if you are at a funeral. The second movement is happy in a plain predictable way. A little boring. And then the third movement has all the revelation. We are at the second movement of this blogpost. Prepare yourself for what comes next.

Organize how I do shopping

Getting my closet organized inspired me to organize something else: how I purchase things to bring into my closet. I was suddenly hit with the realization that I buy things in a chaotic way. I go to the shopping mall with no idea what I am looking for. Grab something that I am attracted to on impulse. Bring it home with no idea how to wear it and there it languishes for years never seeing the light of day. So I created a set of rules for myself before I purchase anything. I call it the fashion shopping plan.

The Fashion Shopping Plan:

Again this wasn’t part of the original challenge. I have a tendency to overcomplicate things by taking on too much. I was worried that by expanding the challenge twice, I was setting myself for failure.  I have now expanded the original challenge far beyond its original intension. I had momentum on my side. I just went for it. Here are my rules for buying clothes.

Wow factor.

 Every single item I purchase must give me the wow feeling when I put it on. No settling is allowed. Anything that is ok, good enough or just fine is rejected.

Must not be a duplicate of something I already own

I never go shopping without an advance plan. I create a list of gaps in my closet. Things that I don’t already own that would be handy to have.

Not a red dress, have too many of those already

This one needs no further explanation.

Fits within my goal

I stated my goal earlier in the post. Every clothing article has to serve that stated goal. No more shopping for a fantasy life.

Is something that I will actually wear

Every new article has to be something I can imagine myself wearing on a day to day basis.

No impulse buying

When I feel that sudden attraction to an item. I leave it behind to think about it. If still want it days later or weeks later I can always return for it. Impulse buying is where I have gotten into trouble to begin with.

Does it go with things I already own?

Unless I can bring it home and wear it the next day, then there is no point in buying it.

Can I duplicate the same look or vibe with what I already own?

During my dressing well challenge, I discovered I wear different things for different moods. I have cloths for when I am feeling romantic, lady like, fierce, playful, serious, intellectual, annoyed or severe. If I already have a particular outfit for a specific mood then there is no need to get a second one. Something might fit with all the rules above. If I can get the same feeling from what I already own then I still don’t buy it.

Does the color suit me?

Figuring out what colors suit me best is a big one. I hold the clothing against my face, if it drowns me out or makes me look dead then I don’t buy it.

Does it require dry cleaning?

Dry cleaning can get expensive. I am lazy about taking things to get dry cleaned and later picking them up. Items that require it are less likely to get purchased.

As a result of these rules, I became super strategic with what I buy.

All the while I was on the challenge I have been documenting my feelings in a journal. Here are some of things that came up for me during that time.

The life changing lessons I learned from my 60 days challenge:

Fashion for me is not about what I look like. It about what happens in my fantasy life. My imagination is signaling to me my desires. Finding a practical way to bring a small little subtle element of this fantasy into my real life is hugely satisfying.

It was around day 55 that I uncovered the real emotional block of my fashion dissonance. I have a fear of success. While most people suffer from fear of failure, I pride myself on not having that problem. In fact, I am the sort of person who jumps into the deep end head first and figures out how to stay afloat afterwards. It was a total surprise that I uncovered that I suffer from it’s cousin malady. Embedded in my brain is this idea that success brings power. Power brings corruption. I am a corruptible person. What if I become a massively successful person and turn into an asshole? Subconsciously, I had this idea I had to become saint like, pure, before I became worthy of success. I associated dressing well with the feeling of success. Since I am an average human full of flaws I was oscillating between dressing like a pauper and then feeling fashionably starved and dressing ridiculously outlandish. Like a person who has been deprived of food for too long and then presented with a buffet of delights. That person might overeat until sick. That is exactly what I was doing with how I was dressing.

This was a huge surprise for me. But, I realize now how I have been standing in my own way in various aspects of my life. It’s like I was blind and now I can see.

I am making the connection of a certain self destructive thread through out my life.

Now that I am aware of the root problem, I need to find a way to remedy it. Find a way to convince myself I am worthy of success despite my many flaws. At least I am aware of the block, which is progress from where I was before the 60 day challenge.

Getting dressed up is a habit. After a while I felt completely comfortable and at ease in my new up styled clothing. The same way I was comfortable in sweat pants because I was used to it. Now I am comfortable wearing a tweed skirt with a cotton shirt. Dressing up used to feel awkward, like I was pretending to be somebody else. Over time that feeling passed.

Plenty is said on the subject of how our attire communicates with other people. How others judge us based on what we are wearing. The big revelation for me is how my attire was about a conversation I was having with myself without realizing it. The way I was judging myself.

The practice of dressing with care on a daily basis is a small and subtle way to communicate to myself that I am worth the effort. The effect is confidence boosting.

Getting dressed well doesn’t require spending money. All that is required is placing attention and care on how you cover your body.