Dressing with and Addressing Self Sabotaging Behaviors


Your appearance tells your story. It shows the world how you feel about, and see yourself. You are sharing with the world a part of your relationship with yourself. So, the question becomes:  What story is your appearance telling? If you don’t like or don’t know the answer; perhaps you should put some thought into how to change that.

We all have at least one person in our lives, possibly ourselves, that is an awesome person. But, for whatever reason they dress poorly and or maintain a slovenly appearance and do not present themselves well. This can be a sign of low self-confidence, low self-esteem, general laziness or all the above. However, it can also just be habit from how you have lived your life and the examples you grew up with. It can also be a sign that you are unhappy.

One of the first signs that there is something wrong with an animal, physically or emotionally, is it stops grooming itself, until it feels better or it passes. People are not much different. When we are sick what do we do? We lounge in our pj’s we don’t do our hair or makeup, and some people don’t shower until they feel better. People that have issues with depression and certain other mental illnesses are prone to the same behaviors. But what about people that are unhappy with where they are in life? Those that don’t feel like they deserve to be happy or successful? People with a negative self-image and they don’t even know where it comes from or why they have it. A lot of times people that fall into these categories fall into a bad habit of Self Sabotage.

Where do these self-sabotaging tendencies come from? Why do we have negative images of ourselves? Have you looked at social media?!  It’s a place to look at for the problem…  BUT is not the start of it. We can go way back to our childhoods. What did your parents do for a living? If one or both of your parents were blue collar workers and they rarely dressed up, you never learned by example. Or if you have siblings that are tall and thin but you are short and stocky… all the family friends saying things like “you’ll get tall and beautiful like your sisters you just have to be patient” Or worse “If you would exercise more you would be skinny like your sisters” People don’t -typically- mean to be cruel, but some of the worst statements a child or young person can hear are cloaked in largely unwanted advice.

 For example:  I have a step-sister and when she was younger she behaved poorly, seeking attention through unseemly behavior. My mom would tell me when my sister made those choices, ” Don’t be like your sister.”  What she meant by this and what my 6-year-old brain understood were two very different things. My mom meant, stay in school, don’t run around with boys, dress like a “lady”, Etc… What I heard was don’t be anything like my sister, so I wasn’t. I did everything I could to be the opposite of my sister, and tried not look like what I thought I was told a person who did those things looked like. 

As I grew up, my opinions stayed the same, don’t dress for male attention, be strong, don’t act weak just so men will take care of you, and don’t cry to get what you want. My sister was and is a beautiful woman. She always looked “good” even if it was to get attention, she dressed fashionably, took care of her hair, always did her makeup, she put out there how she wanted to be treated. So, what did I learn growing up from this; to be blunt, was don’t be pretty, don’t be vain, and don’t be fashionable.


Other life experiences may have happened to you. A girl who grows up in an abusive home may always wear high collars and long sleeves even long after she is free of that environment. If you are very smart but were teased for your glasses they may make you uncomfortable so you keep your head down. Always tall? you likely don’t wear heels and you may hunch if you were teased about it. Don’t like dirt, mud or bugs in a family that loves to go camping? You may dress to have their approval even though you would rather be in ruffles and lace and “girly” fabrics. These all carry over into our adult lives, whether we are aware of it or not.

Recognizing self-sabotage often happens with hindsight. We only see it after we have done it, and its effects have damaged our lives in some way.  Then you start to pay attention to any patterns in your actions, and eventually you will pick up on the emotions that brought you to the situation. Knowing about them will let you act on them before the damage occurs.

I’ll give you an example from my own past of how seeing the actions only after they happen, though I’m willing to be that just about everyone could give their own.

I once needed a job, the store I was working for in a mall was closing. So, I walked around the mall putting in applications to every store that was hiring. I had some good conversations that day, and I ended up having several interviews.

One such interview came about 10 days after I had put in my application at the store. Now in those 10 days between conversation, application, and the interview I had already accepted a job at another store. However, taking my father’s advice I went anyways because it’s good practice and you never know you might get a better offer.

I also realized that I didn’t like their clothing line for a number of reasons, how they did their sizing, how “sexualized” their advertising was being chief among them. I didn’t need the job, so walking into the interview I didn’t care about the outcome.  Mentally I wasn’t taking the interview seriously, I hadn’t done my hair beyond taming it into a ponytail, my makeup wasn’t up to par really, and about the only thing I did right was my body language once I sat down mimicked the manager; laid back and slightly relaxed.

As you might expect, I did not make a good impression and did not get the job, but life moved on. I let the event slip from my memory for several years before I thought about this event again, and realized what happened. Now I use it as an example at least annually on what not to do for interviews.

My attitude towards this job interview sabotaged my ability to get the job. It doesn’t matter that I didn’t want the job, I sabotaged my chances before I even sat down for the interview. If I did it then, how many times have I done it without realizing it? How many times have I done it when it did matter? Once I sat and thought about it I didn’t like the answers I was going to get. I learned more about how I was sabotaging myself in life from this moment of clarity than I have from nearly anything else. Now I have different conversations with myself. They are not as negative; I’m still on this journey too, and I make them more positive. When I have good internal monologue, I dress better because I feel better about myself, and what I feel on the inside I show on the outside.

How do we go from ugly duckling to swan?

So, it’s time to ask yourself if you are ready to change? Moving away from self-sabotage can be a long journey going as fast or as slow as you want to take it. Ask yourself what that change will mean for you, write it down, and keep track of how you feel as you make these changes.

First: stop sabotaging yourself in your thoughts. Quit with the “if only I was “x” or “y” and start going… how do I make this “Z” work for me? Don’t get me wrong, it’s not easy. But you must get away from those negative thoughts.  When I was in therapy, my therapist had me work with a jar that was filled with things that I liked about myself. I was supposed to add to it as someone complimented me or I found something that I liked. And when I felt low, I would read things out loud while looking in the mirror. I look good in red, was something in my jar. When I pulled that, I would often go put on something red, and I would feel awesome that day. Red is now one of my power colors despite a ruddy complexion.

Second:  Stop self-sabotage through actions. Do you pull clothing from the laundry basket or clean clothing pile to get dressed for work? Stop that! Start to respect your wardrobe, you paid good money for those cloths. Take care of them. And by doing so your clothing will look better and last longer, and you will start to feel better. Whether you realize it or not, how your clothing looks affects how you feel about them and yourself. Put your head up, sit up straight… these things make you look more confident. Looking more confident will help you feel more confident. Go back up to step one, and think about a trait you like in yourself – even if you have always been teased for it-  And own it. Once you own it, work it for all it’s worth. To quote Game of Thrones:  Tyrion Lannister to Jon Snow “Never forget what you are. The rest of the world will not. Wear it like armor, and it can never be used to hurt you.”    While this quote does not talk about fashion, it does talk about a state of mind. You are tall – hour glass- husky- short – the list goes on… Dress for it, own it. If you try and hide it, it will still show. Become happy with yourself and your body over time.


Become unapologetically Beautiful!

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