History in the Making

How to Feel Confident in Your Clothing, Style File Friday

Feeling confident in your clothing is an issue that comes up a lot in discussions with readers. I’ve had many readers tell me that they don’t want to buy new clothing or wear certain items because of how they look and feel in it. I can guarantee that every single person (me included) experience this on a regular basis. However, feeling confident in what you are wearing can go a long way to help your mental well-being, and to present a self-assured and capable image. These are my four tips to help you feel confident in your clothing to present the best you possible!

How to Feel Confident in Your Clothing

I am very particular about what I wear. People like to call me difficult, conceited, snobby, and many other names when it comes to shopping, but I am particular for a reason. I know what I like and what I like to see on myself. I don’t want to waste money on pieces I won’t wear for no apparent reason. One major question I ask myself when I purchase new pieces of clothing is: do I feel confident in it? The answer should always be yes! So, how do you go about making sure you feel confident in your clothing? Read on!

1) You Are the Size You Are

As someone who is currently in the middle of losing weight, you have to accept the size you are right now. And I know, that is easier said than done. I have countless friends and readers who swear they “can only wear leggings” because that is all fits. Perhaps that is all that fits in your closet at the moment, but I can guarantee you that there is clothing in existence that fits. I will discuss changes in size below, but you can find clothing that works for you with persistence. Spending all of your time in sweatpants and leggings and tunics in remembrance of the size you used to be isn’t helping you at all. Your body and size is only one facet of you, and it doesn’t define you! My inability to do math doesn’t define me, and your size doesn’t define you.

Note: As someone who is fairly petite, I have a lot of people who make comments about how I am skinny and I don’t need to lose weight and that any clothing fits me. To dispel those notions: I don’t see myself as skinny. I can recognise that I’m not huge, but I’m not the same size I was when I danced daily and that is still something I struggle with. Also, a LOT of clothing doesn’t fit me. I spend a great deal of time searching for and trying on clothing in the hopes of something working. Don’t make assumptions about how other people feel about their bodies!

Preppy casual outfit

2) Have a Wardrobe That Works

As I mentioned, I am currently losing weight. That means that some of my clothing is too small, some of it is too big, and some of it is Goldilocks-just-right. If you won’t accept that you are X size and refuse to buy properly fitting clothing, I can guarantee you that you will not feel comfortable in too-small and random pieces of clothing that happen to fit from eight years ago. If you are a different size than your current wardrobe, buy a few pieces so that you have clothing that actually works for you. I’m not saying purchase an entirely new wardrobe from top to bottom, but 2-3 tops and bottoms can go a long way. It is crazy to see how much of a difference it can make mentally to be in properly fitting clothing. (And depending on how much weight you plan on losing, wearing the older, looser clothes may physically stop being an option after a point!)

Photobooth at RWB's Barre After Hours

3) Leggings are Not the Only Way to Be Comfortable

I am here to dispel the myth that the only way clothing can be comfortable is if they are leggings or baggy shirts. That tells me that you aren’t buying or wearing clothing that fits properly, which is a different issue. I love my Lululemon leggings, but they absolutely send the message that you aren’t putting a lot of thought into what you are wearing. I then ask myself, if you aren’t putting any care into what you are wearing, will you put that care into your work or something else? You don’t have to spend any money to do this- spend an afternoon trying on clothing. Take a range of 3-5 different sizes and see what actually fits you. And try on different styles! If you normally wear long cardigans, try on a structured blazer. And if you live in leggings, try on a pair of dress pants or a skirt. Don’t assume that things aren’t comfortable because they aren’t athleisure! (That would be like saying a book isn’t worth reading if it isn’t Scandinavian crime fiction or any other singular genre.)

Kate Spade Sweater with Plaid J Crew skirt

4) Put on the Finishing Touches

When you aren’t happy with the way that you look, spending more time on what you are wearing can feel counter-intuitive. “I don’t like what I look like, why would I look at myself more?” Well, as someone who puts an #ootd post up on Instagram stories almost every day, what you think you look like and what others think you look like usually don’t line up. Putting those finishing touches on your wardrobe can make a massive difference in helping you feel confident in what you are wearing. Are you wearing that necklace you bought on a road trip with your best friend? Or the ring you got from your parents when you graduated?  Or maybe you just really love that silk scarf? Whatever it is, those finishing touches make an outfit. People can see a difference, and you will feel a difference! And if taking 30 seconds to decide and put on a necklace can make a difference in how I feel, I am all for it.

I also like to make sure that I have a clean and neutral face- that doesn’t necessarily mean make up- and that I have done something with my hair! Usually that just means running a flat iron over it and using a touch of hairspray to control wisps, as that is enough to make me feel put-together. In terms of make up, I can just go with some cover up, a bit of eye shadow, and a touch of blush. None of this has to take forever in the morning! It is just enough to put your best foot forward.

Kate Spade cut out spade necklace for finishing touches on forest green blouse


Do you feel confident in your clothing? What makes you confident?

The Historian
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