Describe a Time You Saw Yourself Wearing Makeup and Thought, “What Was I Thinking?”

Published in: Just For Fun

This tends to happen whenever I come across pics of myself from the ’90s. Back when the pictures were taken, I probably thought I was blazing beauty trails and setting trends, but yeah, that was usually not the case, LOL!


Most of my cringe-worthy moments revolve around lipstick, and I have a ton of terrible pics from my sophomore year in college. I was going through a phase where I loved the look of really dark red lips — so dark they were almost black — and whenever I’d go out at night, I’d line my lips with black eyeliner (!), and then fill them in with the darkest red I could find.

Oh, but it got worse…

After my dark red phase, I was all about dark purple lip liner, on top of which I’d apply a frosty, peachy beige lipstick, and then a dot of clear gloss smack dab in the center of my lower lip.


On top of everything else, I also had really bad hair back then. One day I decided to chop my long hair down to what I called my “Dharma ‘do,” inspired by Jenna Elfman’s then short, flippy hair.

Buuuuut, it didn’t quite turn out the way I’d hoped. The layering, the waves, the shortness of it all? — disaster.

I remember catching a glimpse of myself in the mirror one morning and practically jumping out of my skin! Who the heck is that!? My hair was sticking out in all sorts of crazy directions, like a little brown Ronald McDonald.

Yep, those were rough years…

Describe a time you saw yourself wearing makeup and thought, “What was I thinking?”

Your friendly neighborhood beauty addict,


P.S. Friday is so close I can almost taste it! πŸ™‚

I hope you a had a great, great day today. This is my favorite time of year. Sunny with a cool breeze. Perfect for eating outside, which I did again tonight. When El Hub got home from work, we ducked out for Mexican food (had the fish tacos again, yum!), and now I’m settling down to watch a little TV.

How does your Friday look? More importantly, what are you up to this weekend?


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  1. My wedding. Like an idiot, I didn’t wear waterproof mascara. During the ceremony, i teared up, and yeah, I had black stuff all over my face. lol, Luckily it wasn’t a big ceremony, so not too many people saw it. ha

  2. Chris25 says:

    I remember when I was a clever 12 year old and I thought I could fix my weird disconnected eyebrow (I had a tuft that sprouted away from the brow, like an island) by filling in the space with a black eye pencil.

    I wound up looking like Jafar from “Aladdin”. Not good.

    And there was the time I wore turquoise and purple eyeshadows to school. The idea wasn’t bad, but the execution needed work. I should have blended more and used a neutral to soften the look.

  3. Christina says:

    When I was about to enter high school, I wanted to change up my hair since it was a new chapter in my life and all that jazz. My mom suggested that I go with highlights since I’ve never had them done before. Unfortunately, the hairdresser ended up bleaching and damaging my hair more than making me look all glammed up. My hair became frizzy and poofy with light brown streaks. Needless to say, I spent my freshman year growing out my hair to cut off that mess XD

    • Lucy says:

      the exact same thing happened to me! Though I got highlights when I was 13. Now 19, my hair has never been the same. Dry and frizzy and multi-tonal. My hair is a mixture of very very light brown and mid brown πŸ™

  4. A great majority of my pictures from middle and high school make me cringe. Powder that was supposed to be “translucent” turned up chalky on-camera; hair meant to be “wavy” and “windblown” ended up looking more like “cheap drag queen”… and that’s just the class and club pictures. The less said about the brows – and the eyeliner pencil I used to fill them in – the better.

    Ironically, though, the few pictures where I did look good, face-wise – at any point in my life – came from the times when I wasn’t even trying: all I needed was a little comb-through for my hair, some pressed powder (to take down the shine), some mascara, and gloss or lipstick to complete the look.

  5. Jennifer says:

    Back in high school I would overpluck my eyebrows. There are some pretty awful pictures out there. I try to just laugh it off. I’m still not very going at doing my eyebrows though!

  6. I, too, did some weird looks in the ’90s. My favorite was heavy black “smokey” liner w/ silver shadow plus — and this is the best/worst part — deep plum lips topped with *shimmery ice blue* gloss. I was never full-on goth but I looked half-dead, judging by the pics from that time period. It wasn’t until a school dance when I went out on a limb with a gold/copper look and got tons of compliments that I realized… hey, maybe purple/blue lips aren’t part of my best look after all.

  7. mn says:

    Every era has it fashion/makeup disaster. I don’t think you can really blame yourself if you like to experiment and it was an element of the times- remember those super thin eyebrows sported during the end of the original 90210 era? Or the cobalt blue heavy eyeliner/hot pink lipstick of the 80s? Sure, experimentation has a place but when it comes down to it, classic style wins each and every time.

  8. Heidi says:

    Junior high — Bonne Bell bronzing gel applied HEAVILY all over my NC20-on-a-good-day complexion — not cute!

  9. Marian says:

    I can’t remember any cringe worthy makeup but hair….that’s another story.
    Back in the 70s, I had an afro….lol
    I thought they were beautiful, so I took my very white self and got a very tight perm, picked it out and viola!

    • chudy says:

      ha,ha,ha, Marian
      you don’t know how far I can understand you…’cause….
      I’m from the 80’s…
      I think no need say nothing more…:)
      the overdose make up in my almost child-face was……

      Greats Mariam
      I’m with you…

    • Liz in Paris says:

      Ha, I’m a child of the 70s too. I wanted an afro but my hair was much too thin for it so I washed it and plaited it into dozens of tiny, really tight plaits while it was wet and went to bed like that. Then next morning, mega wavy hair going off in all directions! And I thought I looked cool! Moved on since then (but still listen to 70s prog rock hehe).

  10. merrybelly says:

    haha! My 7th grade year book picture…brown lipliner with frosty pink lipstick and blue eyeshadow πŸ™‚

  11. kalcedon says:

    Silver, gold or emerald green eyeshadow all over the lid with little or no blending when I was first trying up with make-up. Also, I thought I’d do okay applying any kind of chapstick without a mirror, because what could happen… tinted chapstick and lipbalm out of the line of my lips… great :D.

  12. Astrid says:

    I think my most cringe worthy makeup is when I actually bought a foundation lighter than my skintone, convinced by the SA that it would make my face ‘brighter’. Yeah right, it’s more like pasty, someone slapped a chalk on my face. Blergh.

  13. Diana says:

    I once wore a dark purple lipstick to school. I looked like a failed goth.

  14. dzehnie says:

    Too many too many to mention (bows head in shame). From the time I wore foundation meant for white skin (I’m dark skinned for ref) simply because I had it and didn’t want to waste it to when I used a heavily frosted pale silvery green cream stick as lipstick (looking back I think that was cream eye shadow) to when I used black pencil to draw my brows. Pay aTtention to my use of the word ‘draw’. To applying bright coloured eye shadow all the way to my brow bone (think blue, pink and green) or when I never knew eye shadow needed to be blended. Lol. Thank God my skills have improved

  15. Oh God…

    I hardly wore makeup through my university years. I think all I owned was a Maybelline trio (with matte browns of different shades), mascara, and maybe a pink lipstick. For my graduation I decided to wear some makeup, and I used a duo-ended mascara that was super popular back at the time. You know, the kind that has one end of white fiber and the other of regular mascara.

    It was probably the first or second time I used it, and I couldn’t quite figure out how to cover the white with black. I ended up showing up with eyelashes that look like salt and pepper… Not a good look!

    I haven’t used a duo-ended mascara ever since, and I don’t even remember where the photos of that day went. But when I think back about that day, I still cringe a little…

  16. Nina says:

    I have one word for you, PASTEL.

    I cannot, for the life of me, wear pastels. But I never knew that until the day when I smeared baby pink and mint green eyeshadow all over my lids. I looked like … omg I cant even describe how I looked like. LOL!

    So no more pastels for me. Ever. :-d

  17. Sarah S. says:

    To be totally honest, I don’t have to look far back to find makeup I cringe at – I’m always taking risks and now that I’ve got a beauty blog I can shudder and wonder why I posted some things up at all! More specifically, when I was in middle school and high school I usually wore foundaton, powder, and concealer that was too light for me and got major ghost face in photos. I also thought I was cool-toned (I know now I’m warm or at least neutral!) so I’d always be wearing unflattering colors, especially pastel eyeshadows that totally washed me out! Now I avoid pastels like the plague unless I’m going to combine them with something color-saturated, especially near the lashline.

  18. Shannon says:

    Junior High! Ugh. My friend and I got vanity shots together (HORRID pictures…) and it was before I’d really started wearing makeup. We both had this hideous white eyeliner on, and I’m pretty sure I wasn’t wearing any mascara. I think the idea was to try to make our eyes look bigger, but I looked like I was half asleep. Bad decisions, lol!

    • Karen says:

      Hi Shannon,

      I think my friend Jen and I have some of those floating around, too. We got ours done at Glamour Shots at the mall, LOL! So terrible!

  19. Katherine G says:

    I definitely cringe at my middle school pictures. I had huge purple wire framed glasses, braces, eyebrows that showed my Italian heritage, and I always wore my hair in a center parted tight low ponytail. With high school came contact lenses and the braces coming off, but I was still super skinny and awkward. I was known as “horse girl” because I spent a lot of time at the barn training and working with horses. I wasn’t really respected by my peers until high school, which is where I branched out and tried a lot of different things.

    I started trying makeup around 8th grade, and while I was experimental with colorful eyeshadows and even lipstick from time to time, I didn’t really know how to apply it. I always say I didn’t really start looking at least halfway decent until college, which was when I discovered Sephora and had started experimenting with my hair more.

  20. Kate says:

    Oh god…..I was really into super pale foundation in high school. I mean, I am really pale but apparently, I was going for the dead look. I also overdosed on powder during that time. Also, it was the 90s (at least, that’s my excuse) and I was really into shades of brown. Brown eyeshadow, brown blush, brown lipstick paired with that super pale foundation and, to top it all off……overplucked, superskinny 90s eyebrows. So hot!

  21. shailly says:

    the cutest
    hey Karen I have the same ring… wow

    i love your blog !

  22. Kim says:

    Well, I’ve always been a bit blah in the makeup department but I’d have to say my 9th grade class picture where I’m wearing black liner on my lower lash line (applied after heating it with a lighter, of course). Not the most flattering look. My more embarrassing pics usually have to do with my fabulous hair. As an adult, it’s usually “I look so fat” at the time of the picture and “OMG, I look so thin here” when viewing the same picture 10 years later. HAHA!

    • Maria says:

      The makeup artist who does J.LO’s makeup and created that glowy look she always has recommends heating one of the drugs store black eyeliners and applying it to the waterline (I think it’s Maybelline) in this amazing book he published a few years back. You were ahead of your time maybe – cause I don’t know how old you are!!

  23. Ashley says:

    o man, probably when back in high school when i thought matching my eye shadow to my outfit was the coolest thing ever lol. I mean the exact shade no matter how bright. I thought i was THE makeup guru. When i look at pictures from back then it just makes me cringe. I still match my eye shadow to my outfits now to a certain extent but its different because i use more neutrals and i know what the word blending means lol.

  24. Lucie says:

    In middle school I was big on the smudgy thick black liner with no other eye makeup and red lips, and at the start of high school I always used foundation lighter than my skintone and thought it looked awesome…eeek. After getting over the learning curve with makeup though I feel like I’ve done pretty well!

  25. Christina says:

    Blue eyeshadow. I find that it looks really tacky all over the lid. And when I was a young, I thought it was ahhh-mazing. But as a liner (like a colbalt or navy), if the rest of the make up is down played it can be pretty funky and a nice alternative to black or brown. πŸ™‚

    Also, the biggest make up lesson I’ve learned is to work with your features. Our faces are not coloring books, so going overboard with vivid blushers and sparkling eye shadows and heavy make up will make you look far too “done up.” Its better to be seen for you, than your make up. πŸ™‚

    I also got into make up pretty young and I don’t recommend it. I let my daughter (whose 3) play with make up but I hope as she gets older she will benefit from my rough teenage years and aim not to make the same make up mistakes I made. Its wierd how deep cosmetics can be for someone, but I don’t want her to use it like a crutch like I did. I want to teach her about inner beauty and having a wickedly awesome personality and a good work ethic before I teach her how to apply make up. πŸ™‚

  26. Maria says:

    The purple lipliner with peach/frost lipstick was from the late 90210 days. That’s 1994/95 or even ’96 because I remember working for Estee Lauder at the time and MAC was totally catching on and we would wear it and try to find Lauder dup’s to say we were wearing – LOL! I never ever did the black eyeliner on my lips and I’m very thrilled I can say that but I did the opposite of the Sharpie brows and didn’t really wax or pluck much so I had very very thick brows back in the day and the pics are horrific!

    Karen, I Think you should post at least one of these pretty pics you talked us through, it’s only fair!!! πŸ˜‰

  27. Kellie says:

    I had a spiral perm with straight bangs (what I termed “lion hair) all through grade school. I look back on those pictures and cringe. In middle school/early high school I totally rocked the brownish/gold lipstick look. I am super pale and I seriously looked like a dead person. I also went through a semi-goth phase and wore black hoodies all the time with dark purple lipstick. Fun times!

  28. Kali says:

    Love this post idea! Well this is embarrassing but I always wore black liner on my lower lash line. But the thing is…if I still had enough left over from the day before…I would wear it through the next day! This was through middle school and high school! Now that’s cringeworthy!! I didn’t wear any other makeup besides for that. Now I know much better!

  29. Caitlin says:

    In high school I had really bad skin, so I would wear really heavy foundation and powder that in retrospect was way too light for my already super pale skin. Also the trend back then was super heavy black eyeliner, heated with a lighter, then applied all around the whole perimeter of your eyes. I must have looked like a total goth! Not my finest moment.

  30. Caitlin says:

    Oh, or when I tried to do a ‘home’ perm…disaster!

  31. Thank god I wasn’t the only one who did the dark eyeliner as lip liner with frosty pale lips but it was the late 80’s early 90’s so we all looked daft! πŸ˜€

  32. LauraA says:

    My college senior recital pics from 2000 are ones that I cringe at. I’m a redhead of short-ish height, and my makeup styling makes me look like a cross between Bette Midler and Beverly Sills from the 1970s. In other words, pale skin, very darkly smudged eyes with heavy false lashes, bright red lips, overdone blush.

    Not exactly a glam look that stands the test of time. πŸ™‚

  33. Krystle says:

    2 things I look back on and wondered if I was drunk throughout my teenage years, following my friend by tweezing my brows way too thin and brown lip liner just to line my lips, nothing else lol

  34. Krisabelle says:

    OMG, this post and all of the comments are hilarious! Karen, I can’t believe you rawked black liner on your lips! I think my biggest beauty cringe was in high school when I wore this super duper light lilac frosty eyeshadow with a brown frosty Revlon lipstick called Coffee Bean (they still sell it!). I’m on the warm end of neutral and these cool shades did nothing for me! I was also verrrrrry into sporting glitter gel on my eyelids. Blame it on the 90’s!

  35. meghan says:

    Oh gosh, silver eyeliner with purple mascara for sure. But these were at least sheer enough to be subtle.

    I would also take a very very dark burgundy gloss and dot it on over a clear gloss to sheer it out, but I did it without a mirror and I don’t think it ever looked good.

    Face powder in shade #4 out of 6 when I was really a #1, it looked orange!

    I totally did the dark lipstick too, my friends and I used a frosty brown wet and wild and sometimes topped it with black lipstick! Oh middle school…..

  36. meghan says:


    Jerome Russell glitter gel and then later the loose glitter for the win!!!

  37. Vicki says:

    In the 1990’s you couldn’t see my make up for the hideous great big owl glasses I wore!

    I look back now and think “why didn’t somebody tell me what an eejit I looked?” but I guess they were the fashion!

  38. C.Diff says:

    I kind of didn’t understand that the Clinique “airbrush” concealer was really an undereye thing. I put it over some zits and realised later that it had turned circus peanut orange. Another time, back when I bothered to wear makeup to work, I had on Definicils in severely cold weather and it stuck under my eyes in feathery lines. Now I really only use Laura Mercier Secret Camouflage on spots, and that’s about the only makeup I’ll wear to work. πŸ™‚

  39. Ana says:

    I have always been fan of rock/heavy metal/gothic music, clothes and makeup, but my teen years (15 to 18) I got that look I called “Taylor Momsen got smeared panda eyes and crazy too light foundation for my skintone” LOL, I just laugh at those pictures of me… For real WHAT WAS I THINKING?! Then I discovered youtube and the whole makeup world! I don’t wear gothic clothes anymore but my taste for this music hasn’t change haha! πŸ™‚ loving colorful bright spring time!

  40. Ellen says:

    my senior photo, which unfortunately is immortalized on my senior page in my yearbook, on the wall in my house with all the other school pics (I have four brothers), etc.

    It’s actually a really good photo, except for the inch-thick eyeliner I’m wearing. it was before I was good at applying liner, so they were uneven at first, and I just kept slapping it on until the lines were even. not the best Idea I’ve had.

  41. Michele DiCola says:

    I don’t mean to be pompous but I loved makeup from the first day I found it ! People would come up to me and say close your eyes let me see your makeup. It is beautiful!
    I always did a great job ! I still do. The newer products make putting makeup on even easier and more fun. I love reading your blog looking for new & exciting ideas.

    Keep up the great work Karen !


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