Why is it ‘cringe’ to look like you’ve put effort into your outfit? I asked a stylist

“Making everything look effortless shouldn’t be looked upon with pride or be a thing we constantly devour on social media.”

Curated to within an inch of their lives (as much as an algorithm can be curated), my Instagram and TikTok feeds are full of content creators that I love. I scroll and I see two shirts tied together to create something new, skirts layered to create dresses, accessories chosen based on star signs and outfit building inspired by digital filters.

All these out-of-the-box concepts remind me that fashion is versatile, fun and personal. They make me want to put time into creating outfits that are unique and coordinated. The more time I spend on social media though, the more I see the negative perspectives creeping through. 

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Criticism is always lurking, no matter how creative, innovative or inventive you are. There’s this idea I’ve seen crop up recently that outfits that match are ‘too much’ and if people’s outfits look like they’ve been thought about, considered or planned, it’s ‘cringe’. 

As Emily North, the writer behind the Angel Cake Substack says, “I have a sense that through the quiet luxurification of fashion and emphasis on dressing in practical wardrobe staples, we are morphing into a culture where it feels cringe/embarrassing to put thought and effort into a ‘look’,” and I tend to agree.

It’s about looking chic, without looking like you’ve tried. I asked Stylist and Slow Fashion Advocate Jenna Flood, aka Ironic Minimalist, what she thinks of the idea that putting time and consideration into your outfits is embarrassing.  

“For me, it seems strange that dressing up or putting thought into an outfit is ‘embarrassing’ or ‘cringe’. Isn’t it better to put thought into your outfit so that it fully reflects your personal style? Sure, you don’t have to wear a suit and tie to go to the supermarket, but isn’t being able to dress up one of life’s pleasures?” As someone who does indeed dress up to go to the supermarket, I tend to agree. 

The popular ‘wrong shoe theory’ came to mind as I thought about this phenomenon. Is purposely choosing a shoe to mismatch your outfit a way of signposting that you didn’t try very hard? Jenna disagrees, looking at it in a more positive light. “I feel like it pushes you to consider something you wouldn’t have thought [about] before in your wardrobe. [It] helps you to create more looks without buying new things.”

Jenna noted that perhaps even she has fallen victim to dressing down. “I have noticed that I don’t wear my blazers as much as I used to, so maybe this trend has seeped its way into my mind unconsciously. For me, a blazer represents a put-together outfit. So maybe I need to make more of an effort to wear them more often. I do love the ‘boss’ feeling I get when I wear them!”

I feel similarly about wearing an outfit that features matching colours. I have this beautiful light burgundy jacket that I feel I can never wear with my favourite cherry red Doc Martens because it would be ‘too much’. Or perhaps I’ve been, as Jenna says, subconsciously influenced.  

Jenna suggests this whole idea is another trend within itself, just “A way to get us to buy more ‘effortless’ clothing” and I think she might be right. “Making everything look effortless shouldn’t be looked upon with pride or be a thing we constantly devour on social media,” Jenna laments. “Life is hard and we shouldn’t play that it’s easy.”

I can’t help but think this all stems from social media’s current obsession with aestheticisation. We put effort into making our Instagram grids look appealing, but being perceived as someone who overtly curates their content is a bit like being seen naked in public, hence the advent of ‘casual Instagram’. 

“I would rather see (and I have heard many people say this), an unpolished version of things. A dirty mirror in an outfit post (with no apology that it’s dirty!), an unironed shirt with a few wrinkles, an apartment with a bit of mess. I think we need to embrace the mess a bit more,” Jenna says. 

You should dress in a way that makes you feel great, and if that means putting hours of thought into an outfit or matching your handbag to your dress, then that should be embraced. Jenna agrees. “I enjoy creating a look for how or who I feel [like] on that day. Some days are polished with pieces that create a cohesive look, other days are a bit more baggy or oversized to give me comfort.”

If you’ll allow me to be cringe for a moment (in the spirit of this article), there are always going to be haters. There’s always going to be someone who thinks you’re doing too much or too little, who thinks your outfit is too boring, too colourful, too chaotic. Cringe it up, I say.

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