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


12 fashion mistakes header

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

Product Info

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

Kevin Durant white tights
TV Screen Capture, TNT

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
Product Info

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

Nude flats
Photo: ELLE

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

Dress over pants
Photo: ELLE

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

Devil wears Prada
Screen Capture | 20th Century Fox

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!

Posted on on April 24, 2014 / Filed Under: College Life / Tags: , , , , , ,

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27 Responses to “The 12 Most Cringe-Worthy Fashion Mistakes I’ve Made”

  1. 1
    April 24th, 2014 at 9:11 am

    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.

  2. 2
    April 24th, 2014 at 10:26 am

    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

  3. 3
    April 24th, 2014 at 10:29 am

    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.

  4. 4
    April 24th, 2014 at 10:30 am

    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.

  5. 5
    April 24th, 2014 at 10:42 am

    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.

  6. 6
    April 24th, 2014 at 10:46 am

    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.

  7. 7
    April 24th, 2014 at 10:47 am

    I love hoop earrings but I find that they’re so hard to wear without looking tacky!

  8. 8
    April 24th, 2014 at 11:45 am

    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. ;)

  9. 9
    April 24th, 2014 at 12:00 pm

    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.

  10. 10
    April 24th, 2014 at 12:02 pm

    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 :P

  11. 11
    April 24th, 2014 at 12:03 pm

    Aww:( I still like the nude flat and a little hair poof…

  12. 12
    April 24th, 2014 at 1:07 pm

    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. :)

  13. 13
    April 24th, 2014 at 1:52 pm

    Nude flats are very chic! Celebs and professionals wear them all the time!

    I get tons of compliments on my point toed nude flats…

  14. 14
    April 24th, 2014 at 1:53 pm

    I wear running shoes and jeans, but mostly only in the semi-rural area where my parents live. (no one cares there). I used to think that dresses over jeans were super cool, but I don’t remember if I actually got around to trying it.

    I spent an entire summer once in Crocs, and then several summers in sports sandals, which are not the most fashion-forward footwear ever. Thankfully, I have some nice summer shoes now.

  15. 15
    April 24th, 2014 at 2:19 pm

    Ugh, HS was horrible, after spending the first 10 years of schooling in Catholic, uniform mandatory school. By the time I made it to public school in 11th grade, I thought it was cute to wear super flared sparkly jeans (in my defense it was 2001) lol with platform flip flops and a baby tee shirt with a ubiquitous fruit on it like a cherry….paired with an unfortunate flipped out bob and hoop earrings….did I mention I’m a plus size person??? Lol not to mention I thought I was bigger then I was and wore jeans like 2 sizes too big :/ or I was wearing a truly hideous faux velour hoody in a baby pink or blue….uuggghhhh my life!!!!! Lol

  16. 16
    April 24th, 2014 at 2:21 pm

    Not to make it better, but now as an adult, a lot of guys tell me that they like girls with big ol’ hoop earrings bc “all the hot girls wore them in HS” lmao I guess it just stays with you!

  17. 17
    April 24th, 2014 at 2:33 pm

    Crocs!! Sometimes with socks (yes, even knee-high socks)! I also wore Uggs with skirts all the time, and thought it was super cute! I shudder at those pictures. I also went through a period where I thought long sleeve shirts under short sleeve shirts were really cool. Oh and, I used to wear shrugs all the time! I had like 10 and absolutely loved them! Put all those together with my awkward phase (think thick frizzy side bangs because I was too lazy to straighten or blow dry them, braces, acne and metal rimmed glasses) — EW.

  18. 18
    April 24th, 2014 at 3:38 pm

    For about a year in middle school I only wore neon skirts layered with leggings.. Of different colors. I got people’s attention for sure.

  19. 19
    April 24th, 2014 at 5:13 pm

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

  20. 20
    April 24th, 2014 at 10:49 pm

    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

  21. 21
    April 24th, 2014 at 11:09 pm

    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!

  22. 22
    April 25th, 2014 at 1:34 am

    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.

  23. 23
    April 25th, 2014 at 3:05 pm

    Lol I made many of those fashion mistakes but hey I was in high school in 2004 and those trends were “fashionable?” Dresses over pants always makes me think of that JoJo video that was oh so popular in middle school lol.

    My worst fashion mistakes were a flared corduroy mini skirt with track shoes that were a 70s style oh gosh they were awful and a pair of olive green capri length goucho pants oh gosh I feel like Drew Barrymore in Never Been Kissed

  24. 24
    April 26th, 2014 at 9:20 am

    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…

  25. 25
    April 27th, 2014 at 2:27 pm

    What about the trend of feathers in the hair a few years ago? I never made that mistake (my mother wouldn’t let me), but I desperately wanted to be like the pretty girls I saw running around with two or more plumes in their hair!

  26. 26
    April 27th, 2014 at 5:51 pm

    My whole wardrobe until age 17or so was a disaster. At 15: Brightly colored shirts with beach logos from Walmart, paired with brightly colored knit bermuda shorts, and my rich friend’s cast-off Phat Pharm pink and orange sneakers. *Cringe* Very “little kid allowed to dress herself.” 16 was better, but still very run-of the mill. Flare jeans, flip-flops, Aeropostale logo tees, and my best attempt at the hair poof. Oh well, at least I was dressed?

  27. 27
    May 14th, 2014 at 8:47 pm

    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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