How to Get Dressed Series 02: Wearing Sh*t That Scares You

Raise your hand if you’ve got clothes you’re scared to wear.

I’ll be the first to throw up my hand: despite years of work (both personal and professional) around bodies and fashion, there are still specific pieces and general silhouettes that freak me the fuck out.

To clarify, I don’t mean I’m scared of the clothes themselves. I’m scared of wearing the clothes, of wearing clothes that expose my body in a different way or that force awareness of the size/shape of my body.


The above jeans are a prime example. Long story short, I wore these jeans while traveling overseas to visit perspective grad schools. I was stressed and not eating much, so the jeans were looser than normal. I knew that level of not-eating wasn’t sustainable (and that my appetite would come back), so the pants would soon fit differently.

But it kind of got in my head, this idea that they should be loose, and then I got really scared to wear them, because if they weren’t loose what did that mean?* I didn’t want to deal with that. So even though the pants still fit, and I really liked said pants, I stopped wearing them.

*Logically, I just knew this meant I was eating a normal, human amount and everything was totally OK, but having logical thoughts doesn’t always prevent us from freaking out.

Somehow, The Pants (I feel like they need more gravitas in this story) came up with my therapist at the time. Her advice isn’t fun, but in my experience is it truly the only way to deal with these clothes we’re scared of.

If you are scared to wear something, you have to wear it over and over until you’re not scared anymore.

I know, I know: this is so much easier said than done. Who wants to run around wearing things that freak you out? However, if you’ve spent any time in therapy, you might be familiar with this idea that when we avoid things out of fear, we give them more power.

Here I was, hiding these jeans in my dresser and telling myself I couldn’t wear them because what if the fit was different when all along, they were literally just a pair of jeans. Your jeans don’t fit? Buy some new jeans. Simple as that.

I wish I had “easier” advice to give, but this is truly how you work through that fear. That being said, let’s break it down with some tips and advice.

  1. There is a difference between “clothes that scare you” and “clothes you just don’t like.” You do not have to wear things you don’t like. Period. I really liked the aforementioned pair of jeans, which is why I was working to push through that fear and just wear the pants I liked. This is about doing work to open up more clothing options that excite you!

  2. Not every day is going to be the day to wear something that scares you. I can’t give super specific advice here, as everyone is different, but mental-health wise, not every day is a day to push yourself, you know? I have days where I’m operating from a very “resourced place” (as my therapist would say), and I can challenge myself because I have those resources. Other days, I am not operating from that resourced place and know the little things will be up for me. It’s key to know yourself so you can work through that fear when in your resourced place.

  3. Start with small time intervals. You don’t have to don something that scares you and stay in it for twelve hours. I started wearing those jeans again on errands or when leaving my house for a short period of time, and I’d wear them for a little bit for days in a row. It’s hard to go from 0 to 100 immediately, so don’t measure success or failure in this endeavor by those extremes.

  4. Consider your environment. Again, this kind of goes back to the resourced/not resourced place conversation. There are people/situations that make you feel good about yourself and your body, and there are sometimes situations where the people or the setting (or both) make you feel like crap. Ideally, we could walk into any setting and not give a f about what people think/not give up power there, but it’s a journey, to be sure. For example: if I’m going to wear something that scares me, I want to be around friends who are going to hype me up, as opposed to some nightmare family holiday scenario where an overly critical family member is going to make comments about my weight. Consider these differences as you work on defining what a resourced place looks like for you.

Really, we could probably just boil all these tips down to “compassion,” but I hope they add a little bit of padding to the intense advice that is “You just gotta wear the thing that scares you over and over.”

I was doing a major closet clean-out recently and found those jeans. I was pretty sure they wouldn’t fit anymore, but I tried them on. They fit (albeit with little breathing room), but not comfortably, so I took them off and put them in the giveaway pile.

All that time giving them power and making a huge deal of wearing The Pants, and it was that easy to discard them. How’s that for progress? That’s possible for you too, friend: I hope this helps get you started.

What the hell am I doing?