Getting dressed when… nothing feels like me

A new series perhaps???

So we’re clear, I never expected getting dressed to be this deep.

Until the other day I found myself sitting on the edge of the bed crying, dressed in the “perfect outfit” I had planned weeks in advance for our first anniversary dinner.

I was four weeks postpartum, so I spent a decent amount of time thinking about what I was going to wear. My first non-pregnant outing in nine long months! I was excited, but realistic. Obviously, I knew I just had a baby and my body was still recovering. I only wanted to wear something that felt comfortable yet put together. Simple, right?

We were going out for dinner. Nothing too fancy. I envisioned a nice pair of trousers and a button up with some makeup and jewellery to elevate the look. Well, once again, the vision I had in my head of what I would look like didn’t match what I saw in the mirror. As usual, the outfit looked good on the girl from Pinterest, but I hated how it looked on me. The clothes fit, but they didn’t feel right. Something was off.

I tried on another outfit. Again, not right. The shirt was too slouchy. The trousers were too short. Too casual. Too tight. Too loose. After a few more outfits and a growing clothes pile on the floor (you’ve been there too, right?) I started to feel that panicky feeling return to my chest. You see, I’ve been here many times before. I’m a thirty something year old woman after all. Don’t we all have that problem of a closet full of clothes, but nothing to wear?

I wish I could blame this on postpartum body changes (and yes, that’s partially true) but even before pregnancy, getting dressed has been a frustrating and upsetting experience. I’ve been stuck in a pattern of spending hours (and money) trying to put together the ‘perfect’ outfit for an occasion or the ‘perfect’ holiday looks. When I finally sourced the clothing, it didn’t quite look right. Nothing felt like me. In the end, I would settle if the items physically fit my body, then hate how I looked during the event and in photos.

At some point, it stopped being about the clothes. It was deeper than that. Nothing I have worn in the last few years has felt like me, which is very irritating, because I’ve put so much time and effort into curating my wardrobe over the last few years.

So I sat on the edge of the bed and cried. Not dramatically sobbing, just a few quiet tears before pulling myself together so we wouldn’t be late for our dinner reservation.

This is why I care so much about what I wear, I thought. As ridiculous as it seems, not feeling like myself in my own clothes has caused me so much frustration.

What I've been wearing lately. More on that next time...

It feels silly to have something so surface level like clothing affect me in such a big way. When I think back on the last few years, there isn’t one occasion where I remember feeling confident in what I was wearing. Aside from my wedding day (thank God).

Although, I didn’t like what I wore the day after my wedding… I digress.

Looking back, there have been two distinct periods of time in my adult life where I felt consistently confident in what I was wearing. The first was when I lived in Spain for six months during college. All I had was what I brought with me in my suitcase. It was so fun to make different outfits out of the 20 or so items I brought with me. I felt like I had a very defined sense of style then and I wasn’t just dressing like everyone else. I rarely shopped. I worked with what I had and everything went together.

My clothes were minimal, comfortable, yet polished. With less items of clothings, I had to be creative about putting outfits together. The second time I felt positive about what I was wearing was when I moved to Ireland to do my masters degree. Again, I only had what I brought in my suitcase. Less items meant I was more honed in on building out specific uniforms. I re-wore each piece more than a dozen times. I could easily identify gaps in my wardrobe and make considered purchases less frequently. There were no huge clothing hauls. I just picked up a few items here and there when I noticed something was missing that I needed.

Knowing that these two periods of time have something in common (a minimal collection of curated items that forced me to be creative about building outfits and uniforms) I know that if I’m going to cultivate my personal style in this season, I need less items of clothing. And more of the right items of clothing. I’ve known this for a while.

When I was about four months pregnant, I packed away 90% of my closet in a massive suitcase, because my clothes no longer fit and it was hard getting ready in the mornings. I bought a few items (2 pairs of maternity leggings, 2 pairs of jeans in a few sizes up, 4 oversized jumpers, and lots of pyjamas) and built myself a mini pregnancy capsule wardrobe of about 10 outfit combinations that I wore over and over again. It wasn’t anything groundbreaking in terms of fashion, but I did have such an easy time getting dressed everyday.

I even got dressed up for a christening and a few nice dinners and felt alright about how I looked. Basically, there were fewer tears while getting dressed and I rarely got flustered in a state of analysis paralysis. Although there was one dinner I got dressed for that made me cry hysterically when I put my outfit on, but maybe that was actually more to do with the pregnancy hormones.

Getting dressed over the last few years has felt like an endless cycle of trying and failing to locate myself. I’ve finally resolved to finally do something about it. A lot has changed since I was twenty five. I’m older. Six years sober. Married. We went through a pandemic. I don’t go into an office or classroom everyday. I’m no longer living in the city. And now, I’m a mom.

I think that’s what this is, for me. Not a style problem. Not even a body problem.

It’s an identity problem.

To be honest, I’ve always been interested in personal style. I’ve long admired fashion and style Substackers from a distance, because I couldn’t possibly share about my own journey. It’s too embarrassing and not for “people like me” with no identifiable sense of style. But then, this incident of crying before dinner happened again and I figured enough was enough. I need a little accountability and maybe others can relate to my experience and we can do this together.

I feel so silly waffling on about personal style and outfits for this long, but I know that I can’t be the only thirty something year old woman who has navigated an identity shift in the last few years that has left me feeling completely lost when it comes to getting dressed. And when you think about it, getting dressed is something we have to do everyday. Sometimes twice a day if you workout or have a newborn who is constantly spitting up! That’s 365 opportunities to avoid crying in front of the mirror. So for me, it’s important that I at least try to get myself together.

I’d love to make a regular series where I document the process as much as I can here on Substack (where else?) because as I’ve told you many times before, it’s important for me to use this space to share honestly about what’s really going on in my life. And this strangely, frustratingly, has been a bigger issue than I’d like to admit.

So I have a few things I’m working on at the moment (if anyone out there cares and is still reading - thank you!!).

• Creating simple “uniforms” by digitalising my wardrobe

• Being realistic about my lifestyle before purchasing

• Not always defaulting to athleisure

• Re-wearing outfits without overthinking it

• Choosing quality over quantity wherever possible

• Making sure anything new actually fits into my life now

Digitalising my wardrobe - This is the first thing I have been doing to catalogue what I already own so I know what I have before anything new is purchased. I downloaded the Indyx app a while ago and have slowly been creating outfits that I hope to wear over the next few weeks. Indyx is what all the cool girls are using to track what they wear everyday. You can read about it more from Anna Newton who write the Wardrobe Edit on Substack here if you’re interested! She is the one who introduced me to the app.

I’m such a visual person that I need to see everything laid out and if clothes are hidden in drawers I literally forget they exist. I also add any new pieces I am thinking of purchasing and make sure it fits into what I already own and wear. I played around with outfit combinations and feel like I have a great base for spring and summer.

Some outfit inspo from my Indyx

Even though these days I’m staying home a lot with my baby and want to be comfortable, I still want to find a way to feel like myself in this season. I get that other moms might feel like this is NOT the time do make a project out of rediscovering their personal style while so newly postpartum, but for me this is a real act of self care. Also, I’m aware that my body will continue changing over the next few months as I recover postpartum and breastfeed my baby. I want to find clothing that feels comfortable and practical, while also helping me feel confident and put together in the body I’m in right now.

I’m so inspired by other moms here on Substack who write about their own style evolutions. Some of my favourites are Emily Grady Dodge, Anna Newton, Christina Tumminello, Meighan Grady if you want to check them out. I have major imposter syndrome even writing this newsletter, because it feels so self indulgent. But this is something that has affected me so deeply, I must do something about it. So here we are.

Most of my days over the next few weeks will be spent in comfy clothes or pyjamas with my newborn baby girl, but I’m excited to get dressed for the occasional meal or social gathering. I’m going to the US in the summer (hopefully) and Greece in September, which will both be very hot climates. My goal is to not buy anything new for those specific trips and instead collect pieces over the next few months that I can wear day to day OR on holiday for (hopefully) years to come. I’m so sick of buying a holiday wardrobe of cheap pieces that fall apart after a few washes and then never re-wearing any of it!

If you want to follow along (and I hope you do!), this series will be a mix of:

• Honest reflections (the good, the bad, the crying-before-dinner moments)

• Outfit diaries of what I’m actually wearing

• The outfits that work (and why)

• The ones that don’t

• Experiments with uniforms and outfit repeating

• And slowly, hopefully, building something that feels like me again

I’d love to know… has your relationship with getting dressed changed over the years? Since becoming a mom? Or after a big life shift?

Because right now, I feel like I’m starting from scratch.

And I have a feeling I’m not the only one.

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