What to Wear When You Feel Less Confident

What to Wear When You Feel Less Confident

Even though I have a passion for fashion, there are many (and I mean a whole lot of) days when I wear an old t-shirt and shorts with no makeup on and my hair thrown up into a ponytail. This is partly because I’m most comfortable in this type of outfit and partly because getting dressed up takes more effort and hours than I’m willing to give at times.

We all have days when our body feels unhealthy and larger than it actually is (AKA the “gross” feeling) but we still have to get dressed up to go to work or an event. There are some places where yoga pants are just not acceptable. I tend to feel this way when I’m on my period, I haven’t been taking care of my body, or there’s a deeper heart issue bothering me (a lot of times I focus on my body feeling gross as the primary issue instead of the secondary). When I try to ignore the “gross” feeling by putting on jeans or a tighter piece of clothing, it often makes me feel worse because I am relentlessly reminded of the way my body feels.

Thinking about all of this inspired me to write this article; the goal is to show women how to dress out of respect for themselves when their hearts and bodies are feeling less than their best for any reason. It’s crucial for us to learn not to shame ourselves on these kinds of days and to ultimately get to the place in our hearts where we can offer others our best selves as consistently as possible.

Here are three clothing suggestions to sport when you aren’t feeling your greatest:

Option 1: Dresses. When I feel unhealthy and body-conscious, the last thing I want to wear is tight jeans. On days like these, comfort is key. I want to do anything I can to feel better about my body. With any body type, I believe a dress may be the most flattering and comfortable option on a day where one doesn’t feel like putting forth extra effort to dress up. It’s a single, reliable piece that can be thrown on, paired with some comfy flats, and you’re good to go! If you want extra coverage and comfort, throw on a cardigan like this cute Cocoon Cardigan from Target.


Option 2: Pants with stretch. Wearing anything tight and clingy will keep you distracted from what’s truly important during your day. I learned this the hard way many times over before realizing I needed to make a change. If you must wear pants or are okay with wearing pants on a “gross” day (unlike me—I wish sweat pants were considered dressy!), I encourage you to sport a nice pant with a stretchy or looser material. When I absolutely must wear pants on days I feel less than my best, I usually choose looser fitting chinos. Anthropologie’s Pilcro Hyphen Chinos are my favorite kind of chino, and they come in an array of colors.


Option 3: Long and flowy tops. I love the look of a feminine, flowy top with the front tucked into a nice pair of chinos. A flowy top gives the torso amazing coverage but at the same time is flattering on anyone. Rocking a flowy top, in my opinion, is just as comfortable as wearing a roomy tee around the house. It also gives a pretty, ethereal vibe to any outfit. Flowy tops work with slacks, jeans, and even stretchy pencil skirts. I always like to give myself some shape by front-tucking my flowy tops into my bottoms. I love this Relaxed Tulip-Hem Lace Top from Old Navy.


These three simple styles are easy to implement on any budget and can get you through the worst of days. Don’t let the “gross” feeling steal the opportunity to get out there and have some fun—or keep you from doing what you’ve got to do. Give yourself grace and hang in there, friend!

You’ll also like How to Look in the Mirror When You’re Feeling InsecureWhat to Do When You Become Invisible, She Did it Again: When Britney Hurts My Body Image, and How to Lose the Scale and Walk Lighter

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