How to Get Dressed Series 01: When You Have To Try On Something That Might Not Fit (And You’re Freaking Out)

Welcome to a new series I’m doing here on the blog called “How to Get Dressed”! I’ll tackle what makes getting dressed difficult and provide actionable advice and tips. If you’ve got a topic you’d like me to cover, feel free to drop me a line here.

Does this sound familiar?

You’re cleaning out your closet and have created a pile of things that you like...but you’re not sure what fits. Maybe it’s been years since you wore some of these things, or a recent change in your body (which is totally normal and happens often) means some clothes no longer work for you.

You know you’ll give away what doesn’t fit, but in order to know that, you’re going to have to try some things on. And that’s scaring the sh*t out of you.

Trying on clothes may not be a big deal for you, depending on your relationship with your body. But for those of us with any kind of “body image issue,” trying on clothing can be super activating, especially if the fit is called into question because of changes in your body size.


For years I would try clothes on and if they didn’t fit, I immediately thought, “My body is the problem and I need to change it” (AKA make my body smaller). It has taken years of therapy and a lot of hard work to get to a place where I know that if something doesn’t fit or doesn’t work for me, it just doesn’t work: I do not need to change anything about my body.

So, if you find yourself in this situation, here’s what I recommend:

  1. Check in with yourself. My advice here will be a little vague, because you know your mind better than anyone, but before you try anything potentially activating on, ask yourself: “Am I in a resourced place where I can deal with the outcome?” If the answer is yes, try something on! (And if you realize you’re not in a good place for this, you can stop—check in with yourself throughout the process, not just at the beginning.) If the answer is no...

  2. Make a pile/stack/area in your closet for things you need to try on, and wait until you’re in the appropriate headspace to do so. Again, you know your mind better than me, so I can’t say, “In exactly a week you’ll be ready to try those things on!” It might be a while, and you might realize you don’t miss some of those pieces and can give them away.

  3. Acknowledge that bodies change, you may need new clothes, and that is normal and okay! I think sometimes we have this expectation that clothes should fit for years and years and years (because we think our bodies should stay the same for years and years and years). For some people, this might be the case, but bodies change all the time. There are so many different transitions/stages of life that can result in your body looking different. I think it’s important to realize that’s the norm, instead of thinking “I should be the same size I was in high school.” There’s a good chance that dress from 10 years ago may not fit, and that’s OK: as Marie Kondo would say, you can thank it for being a dress you loved 10 years ago and let it go!

I know that in the past, I’ve gotten myself in trouble because I minimize how difficult trying on things can be for me and I just jump right into the process. This often results in me feeling like crap, and in this case that feeling is avoidable. [The flip side to this is you don’t want to put off trying on the clothes for so long that you give the clothes all the power, but that’s a blog post for another day!]

I know how much you might want to finish a big closet clean-out in one go, and you want to just try the damn thing on so you can finalized those keep/donate piles and move on. But trust me, it’s not worth compromising your mental health!

If you see a therapist or mental health professional, this is something you can absolutely bring up with them. This process will look a little different for everyone, as everyone’s brains are different, but my biggest advice is to check in with yourself before you try anything on, and acknowledge that this can be a tough process that may need to happen over a period of time.

Sound good? I hope this is somewhat helpful and takes some of the fear out of trying those “I don’t know if it fits” pieces on.

Please note that the opinions expressed here are my own and that I am not a mental health professional. My content is not intended to be a substitute for professional advice, diagnosis, or treatment. Always seek the advice of your mental health professional or other qualified health provider with any questions you may have regarding your condition.

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