Brette Bliss standing in a park during autumn, wearing all black
Simple Life Series

How I Became More Comfortable and Confident Wearing What I Want to Wear

Many people understand what it’s like to have an image of who they want to be, and what that version of themselves looks like and wears. They also know what it’s like to get dressed in the morning and put something on that doesn’t fit their image of their ideal self. I believe the primary reasons for this are twofold. One, they don’t actually know how they want to dress or they have a vague idea that might change all the time. Two, they aren’t comfortable or confident wearing what they want to wear.

Finding yourself and knowing how you want to present yourself is one step to simplifying your life. When you know your style and have items you love, you spend a lot less time figuring out what to wear, shopping, and purging your closet over and over again. This post is a small part of my Simple Life Series.

I struggled for years not knowing what my personal style was. Before my breast reduction, I was wearing a lot of black stretchy clothing from the maternity section. I was also a cheerleader and my thighs were large and I had a small waist, so finding pants that fit was a nightmare.

I also had a strange duality about me that I didn’t quite understand. I felt like a walking contradiction (cue Green Day). I am a Goth girl at heart, but I also love bright pinks and light things. Picture a Morticia Addams type girl enjoying making flower crowns for kittens. I’m also a minimalist in my fashion and makeup. I was confused about which side of me would be dominant because I thought I had to choose.

I felt I couldn’t mix the styles cohesively and I couldn’t just pick one because it felt too extreme. I only ever felt comfortable doing this when I dressed up. My senior prom dress was a good example of this style awakening that I didn’t see again until about five years later.

Brette Bliss in a flower crown, leather jacket, a pink corset, and a tulle skirt.
Look at that cutie mixing a leather bomber with a pink corset, a shit-ton of tulle and even a dainty flower crown! This was Peak Brette style, yet it didn’t last. I didn’t feel comfortable dressing in styles similar to this on a normal day.

After my breast reduction, I had to start over. Suddenly, none of my clothes fit, then my legs slimmed down because I was no longer a cheerleader. I had no idea what I wanted to wear or how I wanted to dress. I decided to fill my entire closet with black, and while that was comfortable, it wasn’t what I pictured the ideal me wearing. The problem was I couldn’t picture ideal me. I knew she existed, I just couldn’t see her yet.

I experimented with my hair, lost a few pounds, and tried a bunch of different wardrobes while staying within my color palette (black).  I started really getting into fashion. Then when I was comfortable with my size and style choices, I started adding gray, then white, then navy, and now I also have a floral skirt, a baby blue striped skirt, a wine red velvet tank top, and a Slytherin green velvet blazer. I’m slowling adding color back into my wardrobe, but I’m doing it mindfully.

The hardest part of adding things that I loved to my wardrobe, was the fear of showing people the real me through my clothing. I think where most of our lack of confidence and comfort stem from. The fear of being ourselves.

When I was younger, I wanted so desperately to be a cool girl, but the cool girl monologue from Gone Girl ruined that image for me and rightfully so because it was painfully true. I definitely didn’t want to be a cool girl anymore, and I don’t think I really ever did.

I also realized I never was the cool girl and that was what was making me unhappy with how I dressed in the first place. I also realized I had been sexualizing myself to the point of misery. When I stepped away from that, I didn’t know who I was and who I wanted people to think I was because it had never really been about me before. I had never dressed for myself. I was always covering up to protect myself. At that time, protecting myself wasn’t for me, it was about other people.

As soon as I made dressing myself about me, it became easier to determine who I was and who I wanted to be, and how I wanted to present myself to the world.

Five years after high school, I finally know what my style is and I can dress how I like without feeling judged. I can put on a beret and a velvet blazer and leave the house feeling amazing. I don’t think I could have done that at 18. With that said, I still look for affirmation from my friends when I have an outfit that feels really extra.

The process I went through took about two years of experimenting with size and style and one year for actually figuring myself out. I did this process backwards, as it would have been faster and easier if I had figured myself out first.

Without further ado, here is the process I went through to determine who I was aesthetically and how that translated to how I wanted to dress. It all comes down to a series of questions you have to ask yourself, and it’s not a one day self discovery stop either. So take your time.

Another note: This process isn’t exclusive to clothing. It can also be applied to makeup, home decor, and lifestyle.

Who and what do you draw inspiration from?

When you think of the people in your life, on television, or in books that have a style you gravitate towards, who are they? What do they all have in common? What makes them different from each other? Make a list of these people.

If you don’t have any “style icons”, think about the people in your life that you idolize, look up to, or wish to emulate.

Is there a person or character that speaks to you on a personal or even spiritual level? Why do you think that is? Are they quirky and kind? Are they a gentle badass? How does that translate into the way they appear? Its okay to draw inspiration from real and fictional people. Additionally, it’s also okay to emulate them. They inspire you for a reason.

My list includes people and characters like Elizabeth Bennet, Clemence Poesy, Stacey London,Ulyana Sergeenko, Cate Blanchett, Brittenelle Fredericks, Byun Baekhyun, Wendy Darling, Narcissa Malfoy, Morticia Addams, Melinda Gordon, and Persephone.

Also, items can inspire us. Do you love teacups because they’re delicate and beautiful? Do you love airplanes because they are powerful awe-inspiring machines? Think about the things you love or surround yourself with. What do they say about you? Are there parts of these things that say something about the way you dress or appear? Or about how you want to dress or appear? Make a list of these things. Maybe your list has things or ideas on it too. Mine does.

My list of items,things and concepts includes: tea, baskets, black lipstick, pink ribbon, velvet, flowers of all kinds, fresh baked bread, green plants, stars, black cats, white rabbits, stacks of paper, thunderstorms, dark red fabrics, white rooms, handwritten letters, witches, kpop boys, dark forests, bats, bees, and teacups. Really a fairly random set of things, but they all have meaning to me.

How would you describe your personal aesthetic?

Create a mood or aesthetic board just for you. I suggest you go to Pinterest and create a secret board to remove the pressure of putting things in there for other people. It’s important to protect your privacy during this process so you can collect things that are just for you. You can also do it by hand with printed images, magazine clippings, and so forth.

Fill your mood board with any and everything that speaks to you; things that make you happy, things that fill you with love or admiration, things that amaze you. Once it gets really full of pins, go through it. You might notice initially how your interests shift over time, either over the course of days, months, or years. Mine changed significantly over a year. What you need to look for are the things that stay constant through the changes.

When I did this I found that even when I was pinning pretty pastel things, there would be something dark right in the middle, and vice versa. I never actually chose one side of my dichotomous personality. In the middle of a bunch of pink and red flower pins, would be skull art and in the middle of a bunch of dark and moody images, there would be a girl with princess hair tied in a pink satin ribbon. These two parts of my personality and interests always exist together.

I also kept a style Pinterest board for fashion and outfit ideas around the same time. It served the same purpose but was more specific to clothing I liked. I kept it private and then analyzed it after some time like I did the aesthetic board. I came to similar conclusions with it. Both of these boards are public now on my Pinterest.

What words would you use to describe your personal style? Which ones are the most important to you?

This was a step I hadn’t considered initially until I was scrolling through Pinterest and couldn’t find the looks and types of outfits I was looking for. Defining your type of style with key words or phrases really comes down to being able to search and find what you want. Generate a list of words or phrases that encompass your style or the style you are looking for.

My list includes: Comfortable, casual, minimalist, classic, basic, neutral, androgynous, interchangeable, subtle, cozy, gamine, monochromatic, Victorian, simple, practical, feminine, floral, Gothic. Sometimes I add or remove words from my list as I evolve and narrow my interests.

Test out some phrases and keywords alone and in combination. I use “classic”, “minimalist”, “simple”, and “practical” in a lot of my searches, but sometimes I throw in “feminine”, “Victorian”, “Gothic” and “floral” to see what comes up. I combine these phrases with each other and sometimes with similar words.

A phrase I recently searched was “minimalist Victorian inspired fashion.”

I do this because I consider my base and primary style to be minimalist, practical, and simple, but I also like to contrast those styles with feminine touches and Victorian inspired pieces. I wear a mostly black and white androgynous pieces, but also like to add velvet textures, feminine shapes, and Gothic themes.  I don’t think there are any combinations that can’t work if you are comfortable and confident in your keywords and how they represent you. Experiment with what you find, maybe the keywords you selected aren’t an accurate representation of what you are looking for.

What do you want to communicate about yourself to people?

Do you want people to think “chic” or “glamorous” when they first see you, or “practical and simple?”

You are always communicating things about yourself in the way you walk, talk, and do things. What you wear and how you wear it is a message to everyone who sees and perceives you. Someone who wears a scarf around their neck will be perceived differently from someone who wears a scarf around their waist.

Think about what you want your message to be. It may change on the day or your mood, but at its core, there is one very simple message that you want people to take away when they see you. Maybe it’s that you’re always put together. That you are creative and a free spirit. That you are whimsical and modest. Or that you reject stifling beauty standards. Whatever it is, it’s worth saying.

I want people to think “Classic” when they see me. Even when I put on a graphic tee and some loose jeans, I select a classic hairstyle or keep my makeup clean and simple.

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In these photos I move from “masculine” to “feminine” styles while maintaining my “classic” style.

Think about the items you wear daily right now. What do they communicate about you? Do they tell the story you want to tell? Do you want to look put together all the time but your clothes don’t fit quite right? Or do you want people to see you and think glamorous, but you wear yoga pants out of the house 4 days a week because it’s comfortable and easy?

Think about what you communicate and what you want to communicate. Is is realistic to expect you to go from wearing athletic clothing to dresses? If it isn’t because you don’t wear dresses because you wouldn’t be comfortable, then maybe wanting people to think you’re glamorous in the sense of dresses isn’t the direction to go. You have to know yourself, know what feels good, and have realistic expectations.

Its okay to experiment with style and clothing until you find what’s comfortable. Thrifting is a budget friendly way to experiment. Borrowing clothes from friends of similar sizes is too. Experimenting gives you the chance to figure out what you want to say with your appearance while also determining if its the right way to say it. There are so many different ways to communicate one idea; mold that to who you are.

It is completely possible to wear athletic attire and still communicate that you’re glamorous (and sporty too!). Think Serena Williams. You can be more than one thing because you are a complex human being, not a concept or a stereotype.

How do your interests, keywords, and self perception translate into the clothing in your closet?

Does your closet reflect what you want to wear? Do you have some items that do or could? Go through your closet and really get to know your clothes and accessories.

Are the words that you chose to describe you and your personal style the same words you would use to describe the clothing in your closet? Maybe you chose words like feminine and flowy, but your closet communicates uniform and simple. Sometimes you can change how an item communicates by pairing it with other items. Sometimes you have to start over. Its okay to start over, even more so to take your time. It’s not financially sustainable or realistic to go out and buy a new wardrobe in one weekend. It took me a year to get to a wardrobe that is complete and reflects me.

Which items in your closet reflect who you are as a person. Which ones don’t? Which ones could, if paired with something else? Which items do you love but are afraid to wear? Identify what about the item scares you, if you can’t compromise with wearing the item in any combination, you might not love it as much as you thought.

You probably have a set of clothing you wear exclusively and feel good in. Set those aside because those are your comfortable clothes. Then try everything else on, but don’t try on an item by itself, take time to create outfits with the pieces you already love. This is a long process.

Of the clothes you don’t wear, did you buy them because you loved them once? Was it impulse? Did you feel pressured into buying the item?

Why don’t you wear them? Are they the wrong colors for you (You’re a winter and orange just doesn’t look good on you)? Do they not fit? Is it ill fitting (i.e. fits in the chest but not the waist)? Is it something you would have never bought for yourself? Is it old or damaged?

Also think about why you kept the items you don’t love. Was it because you felt guilty for buying it and can’t part with it? Was it a gift and you’re afraid of hurting someone’s feelings? Do you keep it for sentimental reasons?

None of these reasons are worth keeping clothing in your closet. Get rid of them if you can’t make them work or you don’t love them. Even the sentimental items. If you keep something to remember something but it doesn’t make you feel good, is it worth keeping? Take a picture of it and get rid of it, or box it up and store it with other sentimental items.

If you love the item and it just doesn’t fit quite right, think about tailoring it. If you don’t think it’s worth the effort, get rid of it.

Get rid of the things that don’t fit or don’t make you feel great. Get rid of the things you don’t feel comfortable in.

Do you feel good in your clothes?

Comfort equals confidence. You can’t be confident in your clothes if you are uncomfortable, either because you feel like people will stare and judge you or if you genuinely aren’t physically comfortable wearing an item or outfit. You can’t be confident in heels that hurt, and you can’t be confident in a crop top if you are more comfortable wearing modest clothing. There are ways to work around this like buying heels that are the right height and fit for your comfort level or wearing a crop top over another top so you feel covered. By the way, a crop top looks really cute over a collared shirt or basic tee.

Another option is to accept that you may not be comfortable in certain styles and its not worth trying to force yourself into wearing something you don’t like because you think you want to be the type of person who wears that item.

Brette Bliss Mirror Selfie wearing a white tank top over a black tee shirt
I like slip tank tops, but just don’t work in an office where it would be appropriate for me to wear them alone. I like to layer a tight long sleeve tee underneath for modesty reasons. Not my best outfit, but one I am comfortable in.

Do you want to dress in a certain way because it is a reflection of you, or because you want to become the type of person that dresses that way?

One hurdle in finding your style is differentiating between your ideal self and a fantasy self. Your ideal self is you, only the best version of you. This version is comfortable, confident, and knows who they are. You can become your ideal self.

Your fantasy self is a version of you that doesn’t exist in reality. This person is someone you want to be but you would have to change significant aspects of yourself to achieve. You cannot become your fantasy self and be happy because you would have to sacrifice a lot to get there.

This translates to the clothing you wear. Your ideal self dresses in ways that makes you confident and comfortable, while also communicating true things about you to your audience.

Your fantasy self dresses in ways you might want to dress because you think you will become that kind of person if you dress the way they dress. Dressing like a diva won’t make you a diva. Just like dressing like a cowboy wont make you a cowboy. Odds, are you would have to sacrifice something (time, money, a part of yourself, happiness) to achieve a look that doesn’t reflect you as a person and ultimately makes you uncomfortable. Your fantasy self can never be a genuine version of you.

With that said, there are always going to be people who dress in ways that don’t reflect their personality (in your opinion). A girl with slick black hair cut at a femme fatale bob who wears ripped black jeans and leather jackets may also be someone who loves sunshine, bunnies, and pink lipstick. They can be the same person and be happy, comfortable, and ideal versions of themselves.

You might be that person. Maybe there are two sides to you that conflict or contradict each other and you feel torn between them?

A lesson I had to learn was that I didn’t have to choose between the parts of me that contradicted each other. I love androgyny, black, death symbolism, and moody themes. I also love flowers, soft animals, and feminine details. I spent most of my life bouncing back and forth between these, secretly hating the part I wasn’t being at the moment because it didn’t feel like it fit.

Then there was a tumblr post about Persephone that changed my perspective. Persephone has always been my favorite Greek deity. Until this post, I didn’t know why.

Tumblr Post that says "Why limit yourself between choosing between a pretty feminine aesthetic or a dark one? if Persephone can be the goddess of spring and queen of the underworld at the same time so can you. "

Then it suddenly made sense to me why I loved her so much, and it really made me think about why I thought I couldn’t be both. In the end, I was trying to fit into molds. I was either in the pretty feminine mold or the Gothic only wears black mold. I wasn’t happy with how I looked or dressed until I married the two.

If you feel like there are conflicting parts of your personality, embrace them both. Marry your contradictions together, you may find something exciting within combining them that you hadn’t considered before.

In the end

This really isn’t about how you dress, it’s about knowing who you are, what you like, and celebrating that through what you wear and do. You deserve to feel good about yourself and sometimes it takes more than your appearance to accomplish that, but it’s a good place to start. If you think you look good, you will feel good. I know that’s a vast oversimplification, but honestly, confidence comes down to knowing who you are and what you like.

Now that I know what I like, what fits, what looks good, and I actually have a wardrobe that reflects me, I spend very little time worrying about what I’m going to wear and I have more fun getting ready in the morning. I have a very small wardrobe of clothing I love and it has allowed me to simplify that part of my life and love all parts of my personality.

Brette Bliss striking a power pose in a park in the Autumn, wearing all black
I’m much more comfortable and happy knowing who I am, and knowing that I am expressing myself the way I want to


I am a writer and like all writers, I love stories. Fiction, non-fiction, poetry, blog and social posts, pictures, music; they all tell stories. My favorite stories are based in experiences. The human experience is truly magnificent and we all experience it differently. "Brette's Bliss" is a play on my name. I've spent most of my life worrying about whether I am happy or will be happy, and wondering if the meaning of my last name was something that would define my life or if I was simply overthinking it.  As I record my experiences, I learn more about myself and realize happiness is now, not in the past or in the future. This blog is where I share my experiences one story at a time to relive my joyful moments twice and encourage others to do the same. 


  • Laura

    I’m scheduled to have my second BR in a few months and hoping to go from a 48DD to a small B cup. Do you think it’s silly and weird for a 56 year old woman to yearn for the day when she can wear her first lacy bralette? 🙂
    I’ve loved reading all your stories Brette–your true to yourself and that quality is something a surgeon can’t create with a scalpel!! Stay real and all the best for the future!

    • brettesbliss

      How does one respond to such a sweet comment? I am so happy for you and it’s never silly or weird to want something that can make you happier at any age! Thank you so much for your comment it truly means the world to me ♥️

      • Laura

        Thanks for your encouraging words, Brette!
        I too have been through hell and have always hated my “fun bags” as someone once called them–to my face and infront of a group of people. Such a classy guy 🙁 This was only one of MANY comments, incidents and embarrassments I too endured. I am an aunty to five lovely girls and I never hesitate to tell them that they are so much more than a collection of body parts and to expand their beautiful carefree minds and souls and to honor their female spirit and strength.
        Having big boobs does have one bonus–it makes the gals that have them more empathetic and compassionate towards others with health issues.
        When I had my first BR in my middle twenty’s I remember telling others that they should try carrying around a ten or 15 pound bag infront of them 24 hrs a day and see how wonderful big titties really are–that shut em’ real good!
        Take care Brette and rock a bralette for me–one day I’ll be rockin’ one too! can’t wait!:)
        Blessings! 🙂

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