The 12 Most Cringe-Worthy Fashion Mistakes I’ve Made

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My life as a recreational fashionista has had its ups and downs over the past twenty-something years. There were good times – leather jackets, Jeffrey Campbell Litas, little black dresses, and a trusty pair of Converse All-Stars – but there were also the uh, not so good times, like the time I bought a very diaper-esque pair of drop-crotch harem pants. Yikes.

It’s necessary to fearlessly experiment in order to develop your own personal style. But needless to say, not every risky outfit you wear will be a smash hit. To toast at some of these uh, colorful times, I thought it’d be fun for us to take a little walk down memory lane and have a good laugh at my expense.

These are the twelve worst fashion mistakes I can remember making. I’m sure some of them will sound similar to you, too!

Let’s dive right in, shall we?

1. Uggs with Skirts and Shorts

Uggs

Close your eyes, and picture yourself in tenth grade and on a “date” with the guy you have a crush on. You’re probably at the movie theater, possibly at an outdoor shopping center for a local concert night. You might have spritzed on about three squirts too much of Glow by J.Lo or Escada. You may or may not be wearing a Hollister graphic tee. You’re definitely wearing a denim skirt and Ugg boots.

For me though, it didn’t stop with the jean skirts. I avidly wore Ugg boots with mid-length and long skirts (trying desperately to mimic that MK and Ashley look) and again the first year of college with Nike shorts. You read that correctly, Uggs with Nike shorts, and I wasn’t the only girl in my dorm hallway who committed this appalling sartorial crime. In the words of Cher Horowitz, I was “adorably clueless.”

I know I’m preaching to the choir, but there’s a right way and a questionable way to wear Uggs. Sherpa boots absolutely work with pants and leggings on cold days, but unless you’re surfing on a chilly beach, Uggs with mini skirts and shorts just don’t make sense. As for mid-length and long skirts, more structured and polished boots will give you a boho flair without making you look like a frump queen.

2. White Tights

White tights

Although dainty white tights looks totally fabulous on flower girls and children gussied up for Easter Sunday, white tights on grown people just doesn’t look right. Even if you’re a pro athlete, wearing leggings for compression reasons. Just ask Kevin Durant.

3. Running Shoes with Jeans

Women's running shoe

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In my defense, I ran cross country in high school and was frequently very, very proud of my flashy new running spikes. But with Converse, Vans, Sperry’s, ballet flats, old school kicks, ankle boots, riding boots, combat boots, mules, wedges, clogs, espadrilles, wellies, canvas sneakers, high-top dunks, TOMS, oxfords, pumps, and dozens of other styles out there, it seems like any option in one’s closet would be a better choice for an outfit than the pair of athletic shoes you bought to use at the gym.

I of course ignored this conventional piece of wisdom, and have several dozen pictures on Facebook of me in my flared denim and Nike trainers to prove it. So suburban mom chic!

4. Flesh-Colored Leggings

Flesh colored leggings

Product Info

A few years ago, I purchased a pink and baby blue tunic from Forever 21 and bought a pair of light pink leggings to wear with it. It wasn’t until I reviewed pictures from that weekend that I realized it looked like I was running around without pants on – and let me tell you, those Instagram filters didn’t help my cause! Talk about awkward.

Instead of wearing tan, peach, pink, or mocha-colored leggings, I recommend going with a pair that contrasts with the color of your legs. Remember, you can’t go wrong with solid black or charcoal gray!

5. Platform Flip Flops and Sneakers

Spice girls

Official Promo Material | Virgin Records

I blame this one on Bratz Dolls, The Spice Girls, and the cutesy colors that Sketchers came in. I may or may not have also rocked my platform sneakers with knee-high socks – forgive me, fashion gods, for I have sinned!

The one good thing about my old platform flops and sneakers is that I’ll be totally prepared the next time a ’90s themed party rolls around. I’ve got my Baby Spice costume down pat.

6. Hoop Earrings with Athletic Gear

J lo

Screen Capture | Sony BMG Music Entertainment 2001

Jennifer Lopez rocked her hoop earrings with velour tracksuits and it looked awesome. I took this as a sign that I should wear hoops to gym class, tumbling practice, tennis matches, and during powder puff football games.

Not only did this make me look like some kinda crazy high-maintenance diva, but I’m pretty sure it was a health violation, too. Whoops!

7. Hair Bows Made for Children

Hair bow

Photo: Wikimedia Commons

Hair bows themselves aren’t the mistake – heck, we all know how fabulous Blair Waldorf made them look. My faux pas came freshman year of college when I rocked the ridiculously froo-froo ones that were clearly made for a preschool-aged girl. I mean, the teddy bear applique on the bow’s knot should have been a dead giveaway!

Borrowing items from family members is usually a cool thing – think about classic designer goodies from your mom or a hip aunt, dress shirts from your brother, or a worn-in cardigan from your grandpa. But purloining hair accessories from your little niece isn’t the best idea.

8. Nude Flats

There I was, at my first young professionals convention, wearing a spiffy new suit from Express and carrying a fancy black leather portfolio. I opted for ballet flats rather than heels, just because I knew I’d be walking all day long and wanted to stay comfortable. I was thrilled to hand out my resume, chit-chat with some of my old friends already in the work force, and generally impress everyone around me with my new-found professionalism. That is, until I walked by a full-length mirror and realized that, at a glance, my skin-colored matte flats made me look like I was walking around barefoot.

Nude heels, flattering and good. Nude flats with a patent sheen, chunky hardware, jewels, or other obvious embellishments, those are okay. But plain, completely skin tone-matching flats with bare legs? Never again.

9. Flip Flops with Pants

Flip flops with pants

Photo: Wikimedia Commons

I’m not saying that this can’t be pulled off – after all, I’ve seen girls rock flip-flops with linen pants and look totally fabulous. But every picture I see of myself from high school where I’m wearing a pair of flip-flops with corduroys, skinny cargos, or jeans, I shudder oh-so slightly.

If it’s cold enough or if you’re going to an event that’s formal enough to require pants, it is probably a good call to wear shoes with at least a little bit of coverage and structure. Gladiators or sandal wedges should do the trick.

10. Dresses Worn Over Pants

I’ll be honest, to this day I’m still somewhat of a supporter of this trend. It can definitely be done right – for example, a gauzy dress with linen pants, or a short tunic-like dress with a pair of skinny jeans. Totally chic!

I screwed this up by pairing long, patterned dresses with bell-bottomed jeans and yoga pants. Yes, I said yoga pants. Once, I wore a strapless dress with baggy black yoga pants, a denim jacket, and a pair of platformed Sketchers, and actually thought I looked sporty-chic and cool. (On that note, feel free to share any of your own embarrassing outfit stories – they’ll make me feel infinitely better about myself.)

11. Overly Patterned Tights

Generally, I like patterned leggings. They’re more substantial than tights, and have a feel that’s almost more like a jegging or a pair of patterned skinnies than leggings. But heed my warning and be careful when it comes to boldly patterned tights, especially if the patterned isn’t particularly cute.

I have a brown pair of argyle patterned tights from junior year that I tried to wear with a tweed skirt to prove my point. I pretty much looked just like Andie from The Devil Wears Prada on her first day of work.

12. The Hair Poof

So, I never did the full-on Snooki with a Bump-It… but I’m totally guilty of poofing and pinning the heck out of the back part of my crown, like some sort of crazed Southern Belle wannabe. I even used to pair the look with red lipstick and pearls. Being a sorority girl was a blast, but dang did I try my hardest to look like one or what?!

Luckily for well, the world, The Jersey Shore became a thing and the extreme poofing kinda died immediately after. I still look back at old date party pictures and blush a little bit, though.

Spill your guts, girls!

What are some of the fashion mistakes that you’ve made in the past? Did I list anything that you love to rock? What are some other fashion “don’ts” that you live by? What is the most embarrassing thing you’ve ever worn? Be sure to leave a comment and share some of your embarrassing fashion moments!

18 thoughts on “The 12 Most Cringe-Worthy Fashion Mistakes I’ve Made”

  1. My worst fashion mistakes were when I was young and chubby and wanted to dress just like my cousin, who got the pipe cleaner legs gene. Too-tight shirts and short-shorts can look cute, as long as they’re not clearly made for someone a couple sizes smaller. Going the other direction (giant baggy unisex t-shirts) worked out just as terribly.

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  2. Lol, what, now I’m not allowed to wear flip flops with jeans?

    The other things on this list kind of made sense, but that one I don’t understand…

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  3. I was always small for my age, so the only store that fit me (and looked somewhat like I wasn’t shopping in the children’s section) was Abercrombie Kids. I finally got rid of my last pair of jeans a few weeks ago ….and I’m 23.

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  4. I don’t think there’s anything wrong with a decent sized poof…not Snooki extreme, but a lesser one, i still do it and curl my hair and leave my side bangs out.

    Like everyone else, I too wore some pretty embaressing outfits in middle/high school…can we say, shiny silver (think disco pants) flared jeans? Ughhh! And…i had the thickest, bushiest eyebrows ever (ew! then i discovered waxing haha) So many cringe worthy moments!

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  5. My biggest regret is that when I was in middle school, I wore collared shirts buttoned up all the way under sweater vests, and I wore my necklaces outside of the collar.

    I also did the athletic shoes with jeans and flip flops with jeans, and I also wore my fair share of platform shoes/flip-flops. %90 of my clothes came from my older sister, who did most of her shopping at GAP and Abercrombie. lol

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  6. I am guilty of wearing running shoes with jeans 😡 i have started doing it actually because i thought it was a lot more comfortable than rushing six flights of stairs in heels everyday

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  7. My worst fashion mistakes started in elementary school. The only shoes I was allowed to wear were running shoes. So naturally I wore them with dresses, jeans, overalls, everything. Then I had a goth phase from middle school to high school… Dark baggy clothes and pounds of eyeliner. 🙂

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  8. I wear plain nude flats at least twice a week and I get compliments almost every time. They make my legs look slimmer so whatever 😛

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  9. Ok yeah, I’ve def made the jeans with sneakers and jeans with dresses mistakes, but nude flats? Those are perfect for the office! They lengthen your legs and go with everything. I have to disagree on that being a faux pas.

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  10. I don’t think I will ever get over the hair poof. Probably because my hair has always been too long and thin to poof properly, so I missed out on the trend.

    Remember those pants with zippers on the legs so you could turn them into kapris or shorts? That was my greatest fashion sin. I wore the style like four times a week…

    … with my platform sketchers. 😉

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  11. Nude heels are very clearly shoes, whereas the wrong nude flats at a glance look like you’re running around barefoot… which can look strange.

    My worst style year was the 8th grade. Picture Crocs. With socks. Paired with maxi skirts. No regrets, because I liked it at the time, and there’s the comforting fact that middle school seemed to have been a dark time for us all.

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  12. It’s because nude heels are obviously shoes, whereas the wrong nude flats can be mistaken for bare feet at a glance, which can look downright weird in most social situations.

    Also, as for my worst fashion faux-pas… Crocs. With socks. Paired with maxi skirts. And big frizzy hair. Apparently middle school was a dark time for us all.

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  13. The only different between nude heels and nude flats is that one has a heel. Doesn’t make a nude flat any worse than a nude flat. Nude heels look no different than a nude flat. I don’t get why one is a faux pas and one is fashionable.

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  14. Middle school was awful. My DAILY outfit consisted of baggy jeans, a t shirt, a big black hoodie, and beige and pink sketchers. Coupled with crazy eyebrows (thin was in back then… Karma to everyone who made fun of me then because I don’t have to draw mine in) and bad acne. I cringe every time I think of it, but it makes it just a little more okay every time someone tells me I dress like Blair Waldorf.

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  15. Many consider my fashion mistakes to be the day I started being goth when I was 13; I’m 21 now and it’s still here LOL

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  16. Luckily for me, all of my worst fashion faux pas took place in middle school, so there is very little photographic evidence. But if memory serves, in middle school my typical outfit consisted of combat boots, black baggy pants from Hot Topic (which I LOVED because they had like, nine pockets), topped by a tee shirt from Old Navy (my mother said the shirts from Hot Topic were too threatening) (my favorite old navy tee shirt was orange, with a drawing of an owl smack over the chest, with the words hoo dat? Written underneath). This, by the way, was all paired with braces that I matched to whatever holiday was approaching, think glasses, and a truly unfortunate hair cut.
    So yeah. Don’t feel bad.

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