I've Lost My Personal Style – Can I Get it Back?

A closeup of clothing hanging in a closet

As I sit writing this, I’m wearing pretty much the same thing I’ve been wearing for the past 5ish months. The formula is:

(1) Comfortable but unflattering sweater, in a color I don’t particularly care for + (1) uncomfortable pair of pants (usually jeans) + socks I don’t like

If I were going outside, I’d add:

(1) Stained, sad, long puffer coat that envelops my entire body + (1) my grungiest sneakers

Seems like a formula for a self-esteem disaster, right? Yes, you guessed correctly.


A brief history of my style, as follows:

I used to be the person considered by my friends to be the “fashionable” one. I wore deliberately wacky outfits throughout high school – the more things clashed, the better. I religiously read Teen Vogue and watched Project Runway. Once college began, I still maintained my playful sense of style, albeit slightly more sophisticated. The middle years of college were punctuated by trying to fit in on campus. I oscillated between copying whatever my friends were wearing, and going the grungy-college-student route of sweatpants et al. Toward the tail end of my senior year, I started to feel more comfortable back in my old style: a-line miniskirts, turtlenecks, patterned dresses. In the few years post-college, I felt pretty good about my personal style. I continued to hone in. I probably read about fashion more than I ever have. Yet now, at 28, I’ve completely lost track.

A closeup of clothing folded in piles

It’s hard to pinpoint why this began, but my current state is not allowing myself to wear the pieces I know I look good in. I don’t give myself permission to wear my favorite clothes. There’s some kind of mental block.

In the morning, I don’t even spare a glance at the nice pants, the cool shirts. I instinctively grab the uncomfortable, unflattering pieces that I would Kondo right out of my life, if given the chance. The bizarre, almost ironic thing is that I actually have a great wardrobe. I am incredibly lucky to own a number of well-made, beautiful, slow fashion garments. They just never actually make it onto my person day after day.

I am constantly combing through style inspiration. I save several photos to my “Style” folder in Instagram every single day. I know exactly what I’d like to look like, how I’d like to come across through personal style. I know that my favorite clothing colors are shades of brown, white, dark blue, and black. I love wearing linen. I’ve come to love wide-leg pants. These ideas are part of a list in my iPhone Notes app called “Clothing Thoughts” – it contains all my guiding style tenets. But I don’t put it into practice.

...Maybe I’m afraid to wear my best clothing for fear of ruining it? Am I holding it in too high of regard, making it too precious? Not giving it the chance to serve me?

Wracking my brain for the past few weeks, I’ve been hoping to tease out the root of this problem. Does it stem from a lack of respect for myself? Do I not value myself enough to present myself positively to the world? What happened to the me that was before – the me that had fun putting an outfit together for the day, that proudly accepted a compliment when I donned a striking look? I think a current lack of self-confidence is impossible for me to ignore. But I’ve also thought: maybe I’m afraid to wear my best clothing for fear of ruining it? Am I holding it in too high of regard, making it too precious? Not giving it the chance to serve me?


The other day, in part of a conversation, I offered the following explanation for some small behavior of mine: “Oh, you know, it’s because I like to torture myself.” It was an offhand comment, but as I’ve gone about my days since, I find myself thinking about that phrase over and over. I do have a habit of torturing myself. I do this in many ways – agreeing to do things I don’t actually want to do, cramming too many activities into too short a time span, creating a schedule that I know will stress me out by the end of the day.

One of the many ways I torture myself recently, I’ve realized, is by deliberately wearing outfits that I’m fully aware don’t flatter me. It’s like I’m choosing clothing items that will specifically make me blend into the background. Yet, when I wear all of these clothing items together, I can’t help but feel like I’m sticking out like a sore thumb. Why? Because I’m hyper-aware of how bad I look. I’m not seeking compliments here – I know for a fact that these are bad outfits. I don’t look good in them, and I don’t feel good in them either.

A closeup of clothing folded in piles

It’s time for me to slowly, but surely, work on dressing like my best self, even when I’m not always feeling my best. I have to realign my mindset from self-criticizing to self-empowering. It’s tough. I’m not sure when, or how, I came to regard myself with such disrespect, but I desperately want to change it. My fiancé reminded me that I need to focus on the things I enjoy doing – both fulfilling and challenging – and do those every day. It’s a simple enough idea, right? So, I’m working on reminding myself to live joyfully. Putting outfits together that make me feel confident brings me joy – full stop. I’m worth putting the effort in to feel that daily joy.

I’m reminding myself, too, that it’s okay to spill and tear and stain and generally wear things out; that’s all part of life. Clothes shouldn’t sit unworn in a closet. They are meant to both protect and empower us. They can elevate us in our day-to-day activities, however exciting or mundane those activities are. As a freelance artist, I’m usually working from home. But just because I don’t often have to show up for anyone outside of my home space, doesn’t mean I shouldn’t show up for myself.


Have you ever gone through a period of low self-esteem that ended up translating into your day-to-day appearance? How did you overcome the self-doubt? I’d love to hear your story in the comments.