The Search Begins
The search for style can be a daunting task. We all go through our phases, and style matters to some of us more than others. More often than not, if aesthetics matter to you, what you wear and how you look has a direct impact on how you feel. Hopefully it’s less about meeting societal expectations, and more about finding what makes you feel authentically you.
The way I dress has always impacted the way I feel. The theme for my style (and my life, if I’m being honest?) has centered around one thing: comfort.

Neutralizing
Like most, my teens were a mess in so many ways, the least of which had to do with clothes. That said, my primary goal was to feel comfortable – which in this case meant as invisible as possible (middle and high school are not typically kind to chubby kids). Enter: NEUTRALS.
Y’all. I can’t tell you how minimalist my wardrobe was from 2001-2008. Looking through old photos is a blur of beige and white and black, primarily in the form of turtlenecks. And the hoodies. Oh my god the hoodies. Hoodie, actually. A gray one. Front zip. ALL THE TIME. I was not an athlete, nor a skater. I have no explanation or excuse.
Now just to clarify, my love of neutrals didn’t end high school. Exactly the opposite, in fact – it’s stronger now than ever. Photographic evidence below:






Embracing “Risks”
Slowly but surely, I turned a corner. Ok, it wasn’t quite a corner. It was more like a very small curve. When I got my first grown-up job, I started…accessorizing. Yep. It took me until I was a full-blown adult to understand the power of a scarf. Or statement earrings. Boots vs. flats. A cool bracelet, even.
Baby steps doesn’t even begin to describe it, and the baby steps are still happening. Only recently did I embrace the ripped jean. Combat boots. Chokers. Red lipstick (yes, lipstick is an accessory). This shocks even me, but I’m strongly considering a (very subtle…) unnatural hair color. Maybe. It’s possible. (Please don’t hold me to it!).
Regardless of whether I dye my hair turquoise or not, one of my many goals as I age and continue to find my style just like everyone else, is to embrace more “comfortable” risks. In other words, I might get a nose ring, but 9 times out of 10 the waistband of my pants will be elastic. Ya heard?



Finding It
While I’m definitely no expert, I do have a couple of guidelines I try to follow that might help you in your search for style too:
Wear what you like. Seriously. That simple. If you don’t like it, don’t wear it. Even better, if you don’t like it, don’t buy it! I know we all occasionally are gifted a sweater that shocks us with its atrociousness, but let this piece of information free you: you don’t have to wear it. What you wear impacts so much, from your mood to your comfort to your ability to concentrate. If you’re not feeling it, change. (Also sound advice to live by in general).
An extension of this guideline: just because you don’t like a piece in an outfit doesn’t mean that it’s a bad article of clothing. If it fits and you liked it at one point, it might just need some styling. Hang it up somewhere that reminds you to come back to it, and set aside 15 minutes to style it the next time you feel like it. Maybe you’ll find your next favorite thing to wear. Or you might realize you absolutely hate it. Either way, style progress is happening, friends!
Wear what fits. This one sounds like a no-brainer, but I think anybody who’s ever squeezed themselves into a dress that fit comfortably two seasons ago only to find their upper thighs going numb an hour into the night can agree on the importance of this one. No this isn’t from personal experience, why do you ask?
This can be a challenge for many reasons. For one, WHY IS SIZING SO DIFFERENT? How is it even possible that I’m a large here and a 2x here and one number here and another over there and two completely different sizes in the exact same style of jeans (I’m looking at you, Old Navy).
The other main reason this can be challenging, is that bodies change. And if your body is anything like mine, it changes fairly frequently. One month is kale smoothies and walks every night and the six months following it are takeout and…not walks. That shirt that fit me comfortably during Kale Month now pulls in weird places and the buttons are gaping and I now feel like a frump and a half.
My natural inclination is always to first, beat myself up over everything I’ve ever eaten that isn’t a leafy green and everything I’ve done that hasn’t elevated my heart rate. Then look in the mirror for a half an hour and really examine all of the ways this shirt now looks horrible on my body. Finally, in a last-ditch effort to make it work, I dig through my drawer of various shapewear and try desperately to find something that will squish me back into place, usually while grumbling something about GOING. TO. THE. GYM.
It’s taken me years (and is still an ongoing battle) to realize this isn’t healthy and doesn’t help a single thing. I’m preaching to myself as much as anyone else when I say, our bodies change. They get bigger, and smaller, and gravity does its thing, and sometimes we’re more active than others, and not one single bit of that means we don’t deserve to feel good when we get dressed in the morning. So, I challenge you (AND MYSELF): if it doesn’t fit, don’t dwell. Hang it back up, move on to the next, and call it good.



Workhorse Wardrobe
One of the key steps to keeping your style in check, is making sure your wardrobe is working for you and not the other way around. This season, I’m challenging myself to make sure every. single. item. in my closet is working. Not just working, but pulling its full weight.
That means, in the next few weeks, I will be styling every item in my closet.
Correct. Every single item. The ones I haven’t worn in years (there are a few), and the ones that are on my “when I lose 15 lbs” rack (there are even more of those). If a piece doesn’t work, if I can’t find an outfit that is comfortable, practical, and that I love? It’s out. Goodbye.
I’ll be documenting this here, and on social media, so please come along as I create a workhorse wardrobe. Who knows, maybe it will help you in your search for style too!
Stay tuned…
xoxo,
Kristy
This sounds exhilarating! Yay you! I started a smaller version of this and challenged myself to put together outfits with pieces I regularly only wore separately. Example: red knit dress normally through on a scarf but instead I paired with knit and fur vest normally I only wear with long sleeve t and jeans. I hope you find amazing outfits and confidence in payout past purchases. Cannot wait to see them all!
Thank you so much! I can’t wait to get started and bring you all along with me! Also, putting together outfits outside of their normal pairing is SUCH a good idea too! I always get stuck in such a rut…I’m not really sure why I don’t feel like I can wear my denim shirt with anything but that ONE dress. Brilliant, friend! Thanks again for your sweet words 🙂
LOVE this! I also went through a (very long) phase of wearing nothing but t-shirts and jeans because I was too paralyzed with fear to wear anything cool and different. I didn’t know where to start — I didn’t know what I liked, even! I started a Pinterest page and just starting pinning clothes I thought were pretty and soon enough, my personal likes and tastes emerged. I started shopping at thrift stores, too — that helps with getting over the sizing obsession because older clothes run way higher in size number than current clothes and I eventually realized that none of it matters as long as I’m comfortable and happy. 🙂
I absolutely LOVE thrift stores too! I’m all about affordable comfort, and you can’t get much better than that. You make such a good point about the sizing differences in current vs. older clothes. It’s all connected to the fashion industry, and honestly, who has time for that? So glad to hear you’re on the comfortable/happy train with me. Hopefully this little project can help me get rid of everything in my closet that doesn’t fall right in the middle of that venn diagram 🙂