This past year I’ve been going through a style evolution and I’ve only scratched the surface. Yet now that I’ve been showing up here sharing my outfits and “expertise” I’ve been feeling like a fraud. My outfits just haven’t felt quite right. And I know I’m not the only one that may be feeling this way. One’s age doesn’t have to trigger a style change. Yet I do believe the natural progression of one’s life creates an evolution of one’s style because we change. It can be triggered by a new career, a move to a new state, expanding your family or a change in your body.
So I’ve come up with a plan to and I’m sharing the journey with you. It's a 7-step process that I'll chronicle here, on SubStack, and on Instagram, with the hope that it will inspire others who may feel like their wardrobes no longer bring them joy. I won’t tell you it’s revolutionary or nothing you’ve seen before. But it will work for me, it may help you too.
On Monday, I will send out each step, and by Sunday, I will provide an update on how it went and what I learned. (Updates can be found at the end of the post.)
Whether you're feeling stuck in your wardrobe or your clothes don't represent the person you are today, I encourage you to join me. But if you'd rather wait, don't worry. I'll be sharing the complete process in a few months after troubleshooting each step.
STEP ONE: RESEARCH what you like
I think you’ve heard this one before. Find what inspires you. I don’t see a way of around it. Discovering what your style is right now, you need real visual representations of what you like. Or at least I do. So I’ve created a board on my Pinterest titled “My Style Evolution”. You can also create a folder in your phone.
Save photos of favorite past outfits that I want to repeat
Look back at your instagram or Facebook or your camera roll and see if there are any looks from your past that still speak to you today. And that last part is important - what outfits do I want to repeat. Because there are past looks I like but I’m going to wear them again. It’s important to keep the Pinterest board or folder clear with outfits you want to wear now.












Spend 5 mins a day saving images for one week
Pin everything that stands out to you without bias of season or body type or what’s in your closet. Don’t think - will this look good on me? Can I pull this off? Do I have these in my closet? If it makes you stop and think “oh that’s cute, I want to wear that.” SAVE it. I’ll address how to adapt the looks in Step Two & Three.
I’m always saving images. So I have a large collection of outfits already. But if you don’t, I recommend spending an entire week saving images instead of lumping in one day. This eliminates the stress of trying to find a ton of images at once. And it’s easier on the brain to take in inspiration in small doses.
Are you new to Pinterest and the algorithm hasn't figured you out yet?
Like I mentioned, I’ve been browsing Pinterest for a long time so the algothrim already figured out what I like already. But I’m realizing that may not be the case for everyone. Here’s what can help:
Visit these online magazine resources that share really good street style.
https://www.whowhatwear.com
https://www.vogue.com
Try these Pinterest search term. The more you save images you interested in, the more “like” images Pinterest will serve up. So it’s best to do it this for a few days.
Street style
Fall fashion week outfits
Cool outfits
Trending outfits
Search for a style icon you gravitate towards
I’m not going to tell you not to shop, but I’m avoiding buying anything until I know what I need for my new style. I definitely don’t want to buy something only to realize in a couple weeks, it’s not what I want to wear or I don’t need it or it’s just a little bit off.
My thoughts at the end of Step One (11/5/23)
First hurdle I had to work through: How do I get dressed during step one week? I’m primarily working from home so most of the days this week I wore my “comfy” clothes. But on Tuesday I was going into the city to see a broadway show and was immediately was hit with stress over what the f**k am I going to wear? This may be more of a concern to me than most of you but if you’re going through this process you want to look good right? The night before I was racking my brain over what I’m going to wear and whether or not I will like what I pick. Since we’re still in step one, we’ve only begun to scratch the surface of our style but aren’t ready yet to delve into outfits. Yet, we must get dressed. So here’s what I did: Replicate a past outfit you liked. So my suggestion would be to look back at your own outfits first and keep a photo diary of them on your phone. Refer back to them when you need to get “dressed”. Why is this easier than referring to your inspiration images? Because at least you have the clothing items in your closet. So you don’t have to worry about trying to work on adapting an outfit or buying anything new (because we’re not buying anything at this time, right?). Confession: I didn’t do this exactly but I did refer back to an outfit and wore the same kind of pieces, just not the exact same pieces. This is also something you can do. But in the end, I really liked the outfit and felt confident in my choice. And since I felt good, I was thinking about my outfit and enjoying the experience instead. That is my goal and I believe that’s how we should all feel in our clothes.

Also in my struggle to get dressed during this step I realized it difficult for me to remove preconceived notions of how I should be dressing. For example, I kept thinking “well it’s a broadway show in NYC so I should dress up. I should wear something fancy.” While wanting to wear something fancier isn’t wrong, I wasn’t in the right frame of mind to put together an outfit based on an item. My mind was going in a million different outfit combinations and I was questioning each one. And that’s because I'm unclear on what my style is, how I want to dress and whether that items in my closet work for my current style personality. Looping back to why I’m doing this in the first place! So my point is, the “shoulds” should be avoided during this time. Looking back at the outfit I ended up wearing, it’s a look I could wear to work or brunch with friends. I always feel like my looks should be compartmentalized for their occasion - work, hanging out, date night. I think this idea is what gets me into trouble and it’s something I want to address during this process.
Lastly, there is a criteria I want to add to the outfits I’m saving: Save past outfits that make you happy.
of Every Body Gets Dressed shared a question from a reader - what outfit made you happy? And she mentioned that for her it was different from an outfit that was more “flattering”. So I want to add this criteria to the outfits you save. What past outfit did you feel “happy” in? To clarify, this can be in addition to outfits that you liked or felt good in. These saves will be important for later steps.Please let me know if there are any other hiccups that arose during step one that I need to be addressing. Thank you!
Coming Next Week - STEP TWO: Be a Copycat
That's all for now, friends. If you'd like to follow me at @stylingdarya, I'd be thrilled. Additionally, feel free to reach out via DM or the comments below if you have any comments or questions (just please keep it friendly). Thank you for reading this post, it means the world to me that you're here. If you're enjoying what you're reading, please consider sharing this newsletter with others. (And if you have a moment to like it, that would be amazing!) Your support truly means a lot.
Happy Dressing!
xoxo, Darya