Why We Buy: The Ugly Skirt

'Why We Buy' is a series on examining the various motivations for why we buy the things we buy using case studies from my own experience

Mar 22, 2025

Can we all agree that no one loves themed parties? The themes are usually the same: Western, flapper style/ 90s etc. At worst, it encourages cheap, throwaway costumes that will never see the light of day again. At best, it forces one to dig deep in their closet to put together something with a semblance of whatever the theme might be.

Yet, I didn’t mind it at all when my sister told me my niece’s first birthday party was going to be a themed one. Theme: Florals. And my adorable niece will be a butterfly. I mean, come on!! That’s just so darn adorable and also, florals is a good one as far as themes go. Not too specific, and still leaves it up for interpretation.

Or so I thought. As I started scrolling through my Indyx feed trying to find something to wear, I realized I own nothing that fits the theme. No floral prints or motifs embroidered on any of my clothes. This isn’t totally surprising since I lean into typically less delicate feeling clothing, but not even a single piece?!

Before you protest, I’ll admit all things floral are not necessarily delicate. There are plenty of floral things in the world that would fit my aesthetic. So, I start looking.

I do a Google search for floral dress. Side note: I’m convinced Google Shopping has caught on to my tastes. A few months ago, it would’ve shown me Free People (very much not me). Now, Dries Van Noten. Either the algorithm’s getting smarter, or Dries finally bought some ad space.

️So, I’m into Dries and yeah plenty of florals in their Spring collection (groundbreaking?!) but here’s the problem. Anything I love, the flower is too abstract. You can’t even tell it’s a flower. And the obvious flowers, I’m not super into.

I text my sister, “is this floral enough?” She responds, “it’s very abstract”. Now, here’s the thing: that doesn’t necessarily mean a no. Let me back up a little bit before you start hating on her.

I have two sisters, and both of them have a style very different from mine. They are more polished, feminine, delicate than how I dress up. Super cute, but what this means is we often have contrasting opinions on clothes.

So when my middle sister(the one who’s the mother of the birthday girl) says, “it’s very abstract” what she means is, “no, but you do you because I know and respect your style is different.” See that’s the cool thing about her, she has a theme, sure. But she also wants me to be myself, so I knew she was going to be OK with whatever I come up with. However, it was ME who wanted to abide by the theme as much as possible.

This is an interesting one. I don’t particularly care about aligning with expectations. After all, my modifier is irreverent. NOT aligning is part of the point. BUT in this case, I adore my niece SO much that I want to fit in. SO, we keep looking.

Finally, after hours of dead ends, I find it: a stunning Comme Des Garçons floral skirt. A skirt that feels like me. It’s bold. It’s chaotic. It’s weirdly beautiful. The colors crash into each other in the best way. I’m in love. This is the floral I can get behind

.I send it to the sisters group chat, expecting at least one raised eyebrow but maybe—just maybe—a nod of approval.

You see how I said above my middle sister is the respectful one. Youngest sister, not so much. She’s honest to her core—one of the things I love about her. Her response? Brutal. Let me translate for non-Hindi speakers

Me: [sends photo]...For Aanya’s Birthday
Her: What is this?
Me: Skirt
Her: Ugly

My middle sister then responds, always the softer one. She asks me how I plan to wear it. Which kinda top would go with it? Now I am not an outfit thinker so honestly, I don’t know. But I am confident I will figure it out.

This is the thing about a full body yes. I just KNOW. This goes against the common advice of making sure an item works with other items in your closet in a way where you can create at least 5 such items, but this approach has never led me wrong. I also have to credit

Amy smilovic

’s WoF philosophy for this—if you have a closet full of Without Fail clothes, your Have to Haves work when paired with those WoFs. And my closet is full of WoFs. That’s where the confidence to buy this skirt comes from.

Still, for entertainment value, I post our interaction on my IG stories. And guess what? The consensus is the skirt is ugly indeed. Friends who are comfortable enough to tell me the truth straight up say that, others I ask proactively and they uncomfortably answer with a non committal shrug, making their true feelings clear. I buy the skirt anyway.

Let’s examine this a bit. Because it goes beyond clothes.

Buying the skirt at this point would seem like a bad decision—if you’re measuring by popular vote. My sisters weren’t into it. My friends weren’t into it. Even Instagram, which is usually generous with outfit compliments, gave it a collective side-eye.

But here’s the thing: I don’t want to buy it for them. I want to buy it because I know. Not logically. Not strategically. Just instinctively. It felt like me. And that kind of knowing—unshakable, unreasonable, rooted in taste and intuition—is a muscle I’ve learned to trust.

And this is where we zoom out. Because this tiny act of defiance, this quiet, floral rebellion? It’s actually great training for the kind of career (and life) I want to build.

In work, especially creative or leadership roles, the ability to hold your own opinion—even when the room disagrees—is essential. It’s not about being stubborn for the sake of it. It’s about learning to tell the difference between what’s popular and what’s right for you. That’s how you make original things. That’s how you take bets that actually matter.

And guess what? Clothes are a risk-free place to practice this.

There’s almost no downside to wearing something you love—even if people don’t get it. You learn to sit with discomfort. You learn to back your taste. You learn to quiet the noise and tune into your own frequency. These are the same skills that show up when you're pitching a bold idea at work, advocating for a different direction, or trusting your gut in a room full of data.

So I trust my gut and make the purchase.

If you’ve read any of my other 'Why We Buy' stories, this is usually where it ends. But not this time. In this case though, let’s keep following the story to what happens AFTER I receive it.

I put on a random top from my closet with a random pair of shoes. I take a photo and send it to my sisters. Right away, their opinion starts to shift. OKOK we are getting there.

Rough translation: They think is it not bad, maybe even cute

Now, I might have bought this for the birthday party, but that is 3 months away. I am not going to save the skirt for that one event, that’s not how I shop anyway. I plan on wearing it often, before and after the event. The first time I wear it, it is for a Malibu brunch.

I pair it with a simple navy sweater for this result

.Folks? I LOVE it. Beyond love. I feel like myself. I post again on IG, more out of curiosity than anything else. I make it a poll, do people still think this skirt is ugly?

Most have flipped their opinion now! Some still think so. Oh well, it is what it is.

So yeah, the skirt may be “ugly” to some. But to me, it’s a signal. That I trust myself. That I know my style. That I can see beauty where others don’t—and that I’m willing to stand by that.

And honestly? That’s way more powerful than making others happy with my choices. Turns out, the ugliest skirt in the room can be the best decision you’ve ever made. And the best part is my niece won’t care what I’m wearing. But when she looks back at photos one day, I hope she sees someone who showed up as herself—and that doing so is always worth it.

What’s your version of the ugly skirt? The thing you bought (or did) that no one else understood—but you knew was right for you? I’d love to hear it. Drop it in the comments.

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