let's all look stupid
the trials and errors of building the perfect outfit & why it's okay to fail miserably.
Later that night, I got to thinking: Is Carrie Bradshaw still a style icon even when she's wearing an outfit so heinous it provokes a visceral reaction through my TV screen?
The answer is yes… in a world according to me. I’m on my 4th Sex and the City rewatch and this time, I’ve brought my boyfriend along for the ride (he’s thrilled). During every other episode, he exclaims, “Ew, what is Carrie wearing?” And my reaction is typically, “I genuinely do not know.”
It was then that I realized — even though I hold Carrie Bradshaw in such high regard as a fashion-forward fictional character, I hate (probably) 75% of what she wears.
She’s the most inconsistent “It Girl” the world has ever seen. One day she’s wearing the John Galliano newsprint dress (fabulous) and the next, she’s hot pants + a paperboy newscap (unfabulous). And I don’t know whether or not to avert my eyes or commend her for her bravery.
Does the fact that she wears designer pieces trick us into equating that with style?
Do a handful of iconic looks cancel out all the mess in between?
Does her sheer willingness to experiment with her closet with zero shame make her an inspiration?
After it was brought to my attention just how much Carrie misses the mark (in my opinion), I had a revelation… The revelation was that instead of feeling ill, I felt understanding. My judgment had turned into a feeling of warmth. Maybe my heart grew three sizes that day (who knows), but my perspective had drastically shifted.
Enjoying fashion and playing with clothes means often taking risks. I can’t count how many times I’ve put together an outfit that I had lukewarm feelings toward, but wore it out anyways, just to see how it felt. Sometimes, you just have to look stupid to find out what works… and what doesn’t! Hell, maybe Carrie went home after taking on the town in a questionable outfit and said to herself, “Yeah, I’m never wearing THAT again.”
To thine own self be… silly looking (sometimes)
When I was in high school. I would try out so many different looks because I hadn’t pinpointed my personal style. I didn’t even know what cuts, colors, silhouettes, or prints suited me. It was all trial and error.
I remember one time I wore a giant, spotted vintage, faux fur vest to school that my mom got me from Goodwill. I was embarrassed wearing it because it wasn’t the norm… and not a single person was wearing fur in South Georgia. But deep down, I wanted to try it anyway. It felt a bit clunky like I was taking up way too much room, so I was a bit self-conscious.
By the end of the day, I had gotten so many compliments on it (could have been sarcasm??) that I hadn’t regretted wearing it at all. I was glad I took the risk, and now it’s an outfit I’ll always hold dear.
As we become adults, we’re judged for experimentation in this way, and it’s embarrassing to have a fashion flop, so we play it safe instead. But, I think those of us who enjoy pushing boundaries should do so more often and without fear. Why would we even be done experimenting with clothes when we hit adulthood? There is no shortage of fashion I haven’t yet tried and there certainly isn’t enough time in a day to test it all out. The possibilities are literally endless. Playing dress-up in your own closet can be the most exhilarating experience.
What’s the worst thing that could happen if you wear something that doesn’t “hit right?” You may feel a bit uncomfortable, but you learned something. Someone may judge you, but who cares? It’s not that serious.
When your outfit finally makes it out of the camera roll…
I recently went through an outfit crisis, as I tried to style a never-worn piece. Determined to leave the house in my white button-up shirt dress, I tested every possible configuration until I finally reached an ensemble I felt okay (not crazy) about.
And it was actually the queen of silly little outfits that inspired me to style this particular dress. What are the odds?
But it wasn’t easy. The journey involved me taking numerous mirror pictures looking like an absolute dorkus clown, as I desperately tried to put together a balanced look.
The following photos are not for the faint of heart, but I wanted to be completely candid and show the good, the bad, and the ugly of experimenting with your closet!
Vision 1: A classic take — what I had originally dreamt up in my head but I feared it was too plain jane. Was there a way to elevate it?
Vision 2: So, maybe Allison Bornstein’s “wrong shoe theory” could spice things up here. Wanting to match the black belt, I pulled out my platform flip-flops… which led me to the question, “Can a shoe ever be too wrong?” Answer: Yes.
Vision 3: A pop of color could be nice, instead of playing it safe with black. I thought maybe a red short peaking out, paired with a red shoe could be cheeky and fun. I didn’t HATE this idea but my red shorts were bloomers, so it was all bunchy in the back, which looked diaper-esque. Not the move.
Vision 4: White button-ups look great with ties, right? I had just bought a fun one at the thrift store, so now was my chance to style it. Lose the belt, add the tie… and VOILA, I looked like I was cosplaying as a yuppie trying to “let loose” with a tie that says “Hey! I like to have fun!”
Vision 5: For some reason, I wanted the tie to work. I did. What about tie + belt? The more I added, the sillier it became. I was leaving chic shirt dress territory and entering clown town… But it didn’t stop there.
Vision 6: The bozo-ification of Emilee. Shirt + tie + belt + giant shoe. I felt the urge to juggle my phone right then. This was completely absurd.
Vision 7: Would I look less silly if the tie was more simple? I had to see for myself. There were too many sold colors with the blacks and reds, that it didn’t feel balanced. Plus, the red tie was giving me Spongebob vibes… and I always somehow find a way to accidentally dress like him. Seriously, it happens more often than you’d think.
Vision 8: *drumroll*
After all of that closet soul-searching, I went with the very first option… I just added silver accessories (rings, necklace & watch) to “spice it up.” Was I crazy about it? No. Did I feel comfortable? Sure. My friend (pictured) and I even established a clever dress code theme inspired by the look to make it a little more fun.
Sex: Before & After
In conclusion: as natasha bedingfield would say, “release your inhibitions”
It’s okay to play.
As we unravel the threads of our risky ensembles, we find that style isn't always in the eye of the beholder—it's in the courage to be ourselves (and possibly look stupid in the process). So, next time you’re in the throes of a try-on sesh struggling to figure out what’s missing or how to elevate your look, remember, it’s not that deep.
Wear what you dare… even if it ends up being a fashion disaster. Cheers!
Fucking love this attitude! Plus I know my own “most embarrassing” outfits all helped me figure out what I do and don’t like in my clothing tbh ¯\_(ツ)_/ and then give it another decade and a half and you’ll come back around to them like, “oh wait, I was really on to something actually!”
I loved seeing all the versions of your outfit! And you looked fabulous in the end. I have a rule for myself that whatever I wear out of the house, own it. I tell myself I committed to this outfit and it’s on me so I’m going to keep my head high and look like I feel great in it even if I’m full of regrets.
And sometimes when I’m out I’ll see a woman whose outfit looks kind of “wrong” for the context, but I can see that she put some effort into it and I always think, that woman had a vision, she was in her room this morning playing. She might look a bit off, but I applaud her because I can imagine her dreaming up that outfit. There’s something more intimate about it than seeing someone in a very on-trend look.