Developing Personal Style – Building The Confidence To Wear Something New

Building the confidence to wear red lipstick

In the spirit of the upcoming new year, new decade, and new beginnings, I’d like to tackle a question/comment I receive fairly often that goes something like:

I wish I could pull that off.

I’d love to wear that but I’m too short/curvy/shy/etc.

I wish I were the type of person who could wear that.

These statements are all ways in which we’ve convinced ourselves we can’t wear something (of course, there are cases this is true. For example, if you’re the parent of a small child and would love to have a wardrobe full of silk, it may be wise to wait a few years until little sticky hands are no longer a problem.). Maybe it’s a different or more daring style aesthetic. Maybe it’s a beauty look. Maybe it’s a specific garment or color. Maybe it’s a whole new you involving all of the above. We see other people looking the way we want to look and wish we were able to “pull that off”.

I’m an anxious introvert, so I know how deep in our heads, and how hard on ourselves we can get. But the truth is really simple. The key to becoming the type of person that wears “a thing” is…

So, How Do You Become The Type Of Person That Wears A Thing?

The short answer….just start wearing it!

Ok, overly simplistic and dismissive, I know. But hear me out. Storytime!

There was a time when I thought blazers looked terrible on me. I loved them on others and would gravitate toward them in stores, but every time I tried them on, I felt like a poser. I had a whole catalog of reasons why:

  • I’m too short, it looks funny.
  • I’m not stylish enough. I look like a try-hard.
  • I’m not pretty enough to really look good in them.
  • No one else in my social circle wears them. I’ll stand out too much.
  • They’re too attention-grabbing. People will look at and judge me.
  • They just don’t fit me right. No designers/brands make one for someone shaped like me.

One day, I tried on a blazer that actually kinda looked ok on me, and I brought it home. It sat at the front of my closet for a long time before I was brave enough to wear it…but I had taken the first step. Here’s what I did next.

The Key To It All Is Comfort and Confidence.

So, those people who you see wearing “the thing” with ease and like the person you’d like to be? Can you put your finger on what it is? I always noticed they weren’t even giving that thing a second thought. In my case, it was blazers. It was natural for them. They weren’t thinking about it. Weren’t tugging at it. Weren’t fidgeting in it. Weren’t shrinking in the public spotlight for having dared gone out in it. There were just wearing it. They were comfortable, and that gives the air of confidence. Simple as that.

You Become The Type Of Person That Wears “A Thing” By Simply Wearing It Often

It’s super easy to get in our heads and assume we look ridiculous in something. I have the added pleasure of disliking attention, so the whole, “OMG WHAT ARE YOU WEARING?!” from well-meaning friends/family only causes me to avoid making huge changes even more. Here’s my process for silencing the fear:

Step 1: Wear It Around The House.

Try it on with some outfits you already own. Wear it while doing the laundry. Wear it to check your email. Wander around a bit. You’ll pass yourself in the mirror and probably freak yourself out, but each time you do, the shock will be less and less. Pretty soon, catching a passing glance of yourself in a mirror wearing the thing will start to feel familiar. Comfortable. Like you.

Step 2: Wear It In Public, But Around Strangers.

Our friends and family tend to point out when we’re doing something unexpected and different, so don’t do that yet. Instead, wear the thing to the grocery store. Wear it to pick up prescriptions at the drug store. Wear it to make returns at the mall. Short jaunts into public with complete strangers does one huge thing for me…proves I don’t look weird. As far as these complete strangers know, you’ve always worn the thing. The grocery store clerk doesn’t know you’ve never worn that before. To them, you look like just a person, that happens to be wearing the thing. No big deal. No one is pointing and laughing. No children are screaming and running away. You look FINE. Normal. Good, even!

Step 3: Wear It Out, For Real This Time.

Once you’ve calmed your inner voices by wearing the thing around the house (getting comfortable with yourself and how you look) and for quick jaunts in public around strangers (getting comfortable with how other people perceive you), you’ll build the comfort and confidence you’ll need to field the questions and comments from the people you know.

And once that first time wearing the thing is over, you’ll notice the second time isn’t even an issue anymore. Then the third. Then the fourth. And all of a sudden, you’re magically the type of person that wears “the thing”.

But What If I Can’t Wear Something Because It’s Just Not Flattering On Me?

The older I get, the more I dislike the word “flattering”. It describes a state of dressing to please other people, which can be especially loaded as a woman since what’s considered “flattering” is largely based on the male gaze. Instead, I try to focus more on pleasing yourself. Marie Kondo brought “spark joy” to the lexicon and for lack of my own snappy catchphrase, think it works pretty well here too. Also see, Manrepelling à la Leandra Medine Cohen.

Dressing for yourself and your comfort or joy is way better than “flattering”, and I am a big believer in the idea there’s a way for anyone to wear some semblance of a style/look. It’s all about finding the cut/length/version/stying that’s most comfortable for you and your lifestyle. It may just take a little more creativity and work.

For example, in the fashion world, it’s generally undesired to wear clothing that shortens you visually. Style advice is full of ideas to elongate your figure because that gives the most “flattering” silhouette. But here we are in a time where one of the biggest trends is oversized everything. Baggy jeans, oversized blazers, boxy sweaters…all pieces that can visually drag you down and shorten you. At 4’11”, you’d assume I’d avoid such things like the plague, but here I am drawn to boyfriend jeans and long boxy jackets. I’ve just had to take the extra time to find the pieces, styling, and comfort level that works for my situation. Will some people see me on the street and think I look terrible and have no taste to be wearing such things. Sure. But the reality is most people are so absorbed in their own lives and thoughts, they really don’t care about what you do or wear, so you may as well have fun.

My Current “Thing”

I’m currently going through this same process, with “the thing” being bold lipstick. I’ve never been a makeup person, but this past year, I started thinking, “I’d like to be the type of person that wears a bold lip.” So I found a color I didn’t immediately hate on me. And then I wore it around the house. Then I wore it to the mall. A few times. Then after I started feeling comfortable with myself in a bold lip, I wore it to my best friend’s house…and of course she mentioned it…but it was positive and I was emotionally able at that point to believe it and even feel the same way.

I’m not fully comfortable yet…I sometimes still pause in a bathroom mirror halfway through the night and decide to wipe it off…but I’m getting there.

Good luck on all your style journeys, and happy new year!


Join the Conversation


  1. says: Linda B

    I felt like you were addressing this post to me, directly! I so deeply appreciate what you shared here. I am going to try your method with blazers, bold lipstick, and also combat boots!

  2. says: T

    “Manrepelling” — adding that one to my lexicon immediately! You nailed this process (and your look too, every time!), thank you so much for sharing your blogging and fashion story with us Kelly :) I’ve been reading since nearly the start of the past decade and I’m thrilled to still be here.

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