Why Are We Dressing Ugly on Purpose?

An exploration into self-aware fashion, unflattering silhouettes, and why we've given up looking "our best."

You’ve seen it in the wild, but you’ve heard it here first — Dressing ugly is officially cool now.

And before you call fashion subjective or before you even think of the one phrase that can only be described as the bane of my existence:

“Don’t yuck someone’s yum.”

I’m here to tell you that you’re invalid. This isn’t just a case of me being critical (for once). All fashion reason has left the building and it didn’t happen overnight. It’s a phenomenon with layers that’s been picking up steam for years.

Knowingly unflattering silhouettes are being celebrated. Sneakers we used to exclusively wear to mow the lawn are seen on runways. Shapeless dresses. “Wrong” shoes. Clothes that don’t fit. Low-waisted capris that make your legs look shorter than an overly sharpened pencil. The list goes on.

IMO Bella Hadid championed this by prompting the: “Is that outfit cute or is she just skinny?” discussion.

But it’s not just individual pieces. New outfit formulas are being created, not to flatter the body, but to solely spark visual intrigue. Clothes that you’d quite literally be bullied for wearing in middle school are all the rage now. And those participating are completely self-aware.

This isn’t a case of looking back on popular trends and realizing 20 years later that they may have been embarrassing in today’s context. Today is today’s context, and we’re dubbing our own clothes ugly in real-time.

Hell, even Vogue is doing it for us!

Stylists have thrown their own principles out the window in favor of looks that are more daring, exciting, and playful, but blatantly less “attractive.”

“Learn the rules like a pro, so you can break them like an artist.” - Pablo Picasso

The “flat shoe with everything” trend is really making waves in this department. The anatomy of a 2024 outfit seems to be a skirt or pant that hits at the calve + a flat shoe, which = the short leg special. Conventionally unappealing yet we are eating it right up.

When Did We Start Dressing Ugly?

From my experience, it was the moment chunky dad shoes came back into style. I can pinpoint the exact moment that I bought something I genuinely thought was ugly.

The year was 2018 — March to be specific. My Pinterest feed was “popping off” with editorial shoots featuring Fila Disruptors. I knew they were un-cute, but nonetheless, I felt compelled. So, naturally, I took to my private Instagram account and asked the opinion of my friends.

As you can see, 19-year-old me was pretty much the same as 25-year-old me.

The responses were positive. Some people said things like “What a statement!” which could honestly be interpreted as “Hideous! But go off queen!”

I wore them with everything. They were my go-to sneaker and ever since then, I have been living In Big Sneaker Land (even though skinny sneakers are all the rage).

Me & the beloved ‘Squidward’s House’ ft. my Fila Disruptors. Dad on vacation-core in 2019 was a BIG DEAL.

I think the “ugly shoe” movement was just the first step in normalizing ugly pieces.

But why do people do it? For me, wearing something I know isn’t necessarily cute in a conventional sense is fun. Playing around with clothes is exciting. It’s new. It’s almost like I’m a part of my own inside joke and those who understand, just get it. And those who don’t? Well, that doesn’t matter too much to me. They’re not going to hurt my feelings for thinking what I’m wearing is ugly… I literally agree with them. Fashion doesn’t need to be so serious ALL the time.

The Bigger Picture: How Has Our Culture Contributed to “Ugly on Purpose?”

My initial thought about why this is happening is of course a mixture of different opinions.

We’re Bored

Fashion is cyclical. And anyone who regularly listens to video essays about fashion would probably be rich enough to buy a Birkin if they got a quarter for every time they heard that sentence.

We live in a time where fashion history and trends from decades ago can be dug up in about 3 seconds. We have immediate access to inspiration from all eras of style via the internet. That being said, it seems that because of this (and the unfortunate nature of micro trends thanks to social media), we’ve mowed through just about every possible trend there is and seen them styled in all the “right” ways according to the style makers. We’re fatigued. We want something new.

The solution? Break rules. Take those trendy pieces and style them in a way that no one has ever seen mainstream-ly speaking. Be unflattering and know it. The self-awareness is an accessory in and of itself. That’s what makes it different this time around.

Rejection of “Flattering”

I’m going to a casual party. Do I wear the mini dress that hugs my body in all the right places or the casual shapeless maxi dress that is cool and comfy but swallows me whole? Depends on the mood.

Sometimes I’d rather dress in a way that makes me feel effortless and cool rather than in a way that accentuates my curves. I dress for myself and sometimes it feels a lot better to wear something conventionally unflattering. Sometimes, it feels like I’m being more true to myself by wearing certified “ugly” clothes.

Why do you think most of us wear mom jeans? Sure, it makes your backside look good if they hug you in a very specific way when you bend one leg and hold it up in an L-shaped position (yes this was too descriptive for me not to be referring to myself). Most of the time, you look stumpy and wider than you actually are. But they’re comfy, I like the silhouette, and it isn’t my goal to be hyper-feminine every time I leave the house.

What Do the Masses Think About the “Ugly on Purpose” Phenomenon?

To provide a more well-rounded view of this, I had the bright idea to do some field research… and it completely backfired, because I made the deadly mistake of posting to the wrong Reddit crowd (R/Unpopularopinion).

To be fair, I went to several fashion-related groups first and I was always somehow breaking a guideline by posting this discussion. I think the AI moderators take offense to the word ugly. They’re just not about it. Silly, stupid robots.

My original post that got destroyed to oblivion by incels & angry people. Yikes.

Anywho, I got lit up with a trillion comments from people getting angry at me for calling people’s clothes ugly… which of course was not the point I was making.

Hilariously enough, the comment section was SO hostile that the entire post got taken down after an hour. Luckily enough, I screenshotted everything for #entertainment and #journalism.

The phrase “wrong crowd” does not even scratch the surface of what I experienced in this comment section. More like, “wrong angry mob of people who hate their life, just got off work, and are looking to cause problems.” People also seemed to think I was mad about this phenomenon for some reason.

As you can see here, the comments get more hostile as we move down. Exhibit A:

I don’t think people care that much about fashion and just put on what they think looks good on them, regardless of if someone else thinks it’s ugly or not.

Since when is fashion not subjective?

Beauty is in the eye of the beholder. People don’t have the same tastes. If you see someone wearing something you think is ugly, don’t look at them. That ugly outfit could be their favorite one.

Do you have any actual supporting evidence for this claim of people intentionally dressing in unflattering styles, or is this a conclusion you have drawn based on your subjective opinion of their fashion sense?

Which… has been happening for eternity so why now is it a problem?

You think fashion houses and influencers don’t know what goes together and you do? Are you the head of five major fashion houses?

I also had a fair amount of people saying that I’m “too old” to understand current trends, even though they have no idea how old I am. Exhibit B:

You might just be getting old.

Nah, you’re just getting old and are no longer the primary target market for most fashion. Your parents’ generation felt the same about what was fashionable when you were young.

This has major “old man yells at clouds” energy.

On the bright side, there actually were some genuine responses from those who understood the discussion I wanted to have and provided their opinion on the trend. Exhibit C:

I think people are going for an ironic “I don’t care” look.

Honestly, humans can do with a lot less obsession and emphasis on looking hot and sexy.

I think “anti-fashion” can be a lot more fun than traditional fashion, since there are way less rules that go into it.

My favorite response was from someone who said this all reminded him of ‘The Uglies’ — a Judge Dredd comic series that features citizens that make themselves ugly on purpose to achieve uniqueness.

Now that’s what I call commitment to #fashion.

Closing Thoughts

The older I get, the more I appreciate fashion as an art form, rather than it simply being “clothes.” Silhouettes excite me more. Creating new shapes is fun. Fashion is playing dress up. Nothing is ever so serious. Rules are meant to be broken. That’s art.

Dressing ugly on purpose is freeing. Freeing from societal standards that tell you that you have to dress in a way that flatters your shape. Freeing from the opinions of others. When the only opinion you care about is your own (when it comes to what you’re wearing), I promise, you will unlock a new a level of fun when you get dressed.

I’ll leave you with this:

Move aside Bella Hadid, Spongebob did it first.