5 Fashion Mistakes I’ll Never Make Again

Let’s face it: we’ve all made fashion mistakes. From that 2 a.m. impulse buy that screamed “good idea” until the try-on, to the fashion faux pas of a tight skirt ripping in the office stairway during a fire drill. These are the relatable style bloopers we laugh about later.

But what about the personal fashion mistakes that dim your true self? The ones where your style took a backseat, leaving you feeling like a lesser version of yourself? Those are the real mistakes—the ones that spark wisdom and sharper fashion sense once the lessons sink in.

In this post, I’m diving deep into my style journey, sharing five fashion mistakes that once ruled my wardrobe, the hard-earned lessons they taught, and how they’ve shaped my life today. This gets vulnerable because fashion’s deeper side often goes unspoken. Maybe you’ll see yourself in these stories, maybe you won’t—style’s as unique as your personality. I hope my journey, as I rediscovered my personal style, unlocks something profound for you, freeing you to embrace your best fashion year yet.

Who’s ready to get real with me? Let’s go.

Mistake #1: Too many black shoes

Black shoes are a wardrobe essential—safe, versatile, and stylish with countless outfits. But this mindset led me to one of my biggest fashion mistakes: oversaturating my closet with black shoes, leaving me in a monochrome rut.

Surprisingly, this style mistake came later in my style journey. My “old wardrobe” (more on that later) was a rainbow of colors and patterns, with shoes to match every vibe. Then, after a major closet clearout years ago, I started over, footwear included. Working in an office, I bought shoes for maximum versatility, often ignoring my gut’s pull toward “fun” colorways for practical black pairs. I was playing it safe, scared of overconsuming or overspending. Fast forward, and my closet’s a black shoe parade—pumps, boots, flats, you name it.

This fashion blunder taught me balance: versatility is key, but so is personality. Now, I’m curating a wardrobe with intention, mixing a few classic black pairs with vibrant pops of color. Though I’ve no minimalist wardrobe, I embody the wisdom of prioritizing quality and personality over quantity.

My lesson? Don’t let “safe” stifle your style—choose pieces that reflect the real you, inside and out.

Mistake #2: Buying for style over fit

Fashion trends and aesthetics can inspire your style, but one of my biggest fashion mistakes was letting romanticism trump wearability. Chasing a certain look often led to wasted money, time, closet space, and feelings on items that just didn’t work for me.

I had a “come to Jesus” moment in my early 30s with shift dresses. Obsessed with the 1960s mod vibe—think Twiggy in chic, straight-cut frocks—I bought every shift dress that wowed me, imagining myself as a retro icon. In reality, they hung shapelessly, catching on my butt, giving colorful potato sack, and fueling the internalized shame I had for my body. Despite this, I kept chasing the aesthetic, ignoring how poorly it suited my body, until I finally acknowledged this style would never flatter me. Each unworn dress sat neglected, cluttering my closet and mocking my misplaced enthusiasm.

This blunder taught me to prioritize fit over fantasy. I now prefer to dress for my body type, choosing clothes that flatter my shape and boost my confidence. I lean into soft classic style, selecting timeless pieces that feel right, and trusting what my eyes show me when a fit or neckline looks off.

My lesson? Stay grounded in what works for your body in real time. Choosing fit over aesthetic frees you from future style mistakes and a wardrobe full of Goodwill donations.

Mistake #3: Allowing others to influence my OOTD

Inspiration is the heart of fashion, drawing from nature, eras, or others’ creativity, but one of my biggest personal fashion mistakes was letting others’ opinions override my style. When influence becomes control, it drowns your authenticity in a sea of inauthenticity. I learned this the hard way, dressing to please instead of to express.

In my early twenties, I happily expressed through my bold wardrobe, fueled by a great job and a zest for style. But my romantic partner’s backhanded comments, cloaked in pleasant tones, judged my outfits when we’d join his friends or family. One night, dressing for his friend’s party, his critique hit hard; I changed my outfit to avoid conflict. At the party, standing in a circle of small talk, I was silently seething, borderline plotting revenge for this violation against my very being. I faked an illness to escape early, feeling sick in spirit, not body.

This style mistake taught me to reclaim my confidence. I now build a wardrobe that reflects my personal style, not others’ expectations. I focus on how to dress better, choosing outfits that make my light shine, unbothered by anyone’s judgment or jealousy.

My lesson? Your style is your voice—don’t let others mute it. Embracing what feels authentic frees you to make fashion a joyful, spirited adventure.

Mistake #4: Disregarding color choices

Some say there’s no bad color, only bad lighting, but my style mistakes prove otherwise. Ignoring color choices kept my wardrobe stagnant, clashing with my natural palette. It wasn’t just a fashion misstep—it was a disconnect from my authentic self.

In my early twenties, family jokes about going gray throughout my life, paired with a partner’s nagging about my first grays, sparked a 15-year henna hair dye obsession. Henna’s warm, fiery tones pushed me toward fall palettes—think golds, oranges, and warm jewelry—ignoring my neutral-cool undertones and icy eyes. My hair and scalp suffered (a story for another day), and my style veered off course. For years, photos looked off; I couldn’t pinpoint why.

The thing about henna is that it’s very warming, color-wise. As the silver continued to multiply on my roots, the overtone increased in warmth with every root touch-up. I naturally began to gravitate toward very warm colors, fall palettes, and gold jewelry–completely losing touch with my natural undertones, which were very cool and icy.

A few years ago, I ditched the dye, letting my gray, silvery, and ashy brown roots shine through. The contrast—warm henna against cool natural strands—revealed the color clash. My wardrobe, makeup, and jewelry no longer worked, exposing a culture shock: I’d been living a lie, hiding my true colors out of fear. I cringe at old blog post photos, but embracing my bright winter palette feels like a second chance.

Now, I shop my closet with intention, choosing icy blues, silvers, and cool tones that harmonize with my natural hues. I even enjoy wearing bold lip colors.

My lesson? Our perceived flaws—like gray hair—are often our greatest assets. Matching your style to your true palette unlocks an authentic, vibrant wardrobe and makes shopping a breeze.

Mistake #5: Purging my closet due to trauma

Decluttering can be cathartic, but one of my worst fashion mistakes was purging my wardrobe in trauma’s grip. Reeling from rejection, I erased pieces that embodied my essence, leaving a void I’m still healing. It was a devastating loss of my true self.

Storytelling was my shield against rejection—school tales spun to seem cool, an abusive, older boyfriend to boast about in my senior year of high school. In college, I turned those stories inward, lying to myself instead to dull the pain. The rejections continued.

In my thirties, a betrayal crushed me. I put off the weight of that rejection because I was simultaneously dealing with the loss of my stepdad. But, during lockdown, I decided my wardrobe—tied to “bad energy”—had to go. In one weekend, I slashed it to a few basic items, justifying this was the only way I could step into my “new life”. After all, these pieces were just things and meant nothing. Secretly, my heart was breaking.

That silent devastation lingers, regretting vibrant pieces that represented me: bold and eclectic. I now find myself thrifting and hunting for unique finds to revive my maximalist edge. Budget shopping fuels my creativity, timeless essentials ground my outfits, and each new article I author fuels my passion for personal style.

Eleanor Roosevelt said it best:

“No one can make you feel inferior without your consent.”

Though the rejection from others is crushing, the deepest rejection I experienced was my own.

The lesson learned? External rejection is often a mirror of how we’ve rejected ourselves. The best way forward is learning to embrace and love ourselves fully. That’s what my journey is all about.

Afterthoughts

My style journey is a vibrant tangle of fashion mistakes and hard-won truths. From black shoe overload to mod dress flops, dimming my light for others, clashing colors, and purging my closet in trauma’s shadow, each misstep led to my eclectic, maximalist self. These aren’t just wardrobe fails—they’re my path to reclaiming myself.

Your style is your essence, pure and unfiltered. Whether you’re healing from silent devastation or finding catharsis in your personal style, your wardrobe is your voice—let it speak. Trauma nearly stole my truth, but I’m rebuilding, thrift by thrift, outfit by outfit. Reflect on your own fashion mistakes, search your heart, and wear your truth fearlessly. Here’s to closets that pulse with us—fun, life-giving, and free.

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