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Our Biggest Most Embarrassing Fashion Mistakes

Author: Lolly Gautier-Ollerenshaw

In recent years there’s been something about January that’s made me rather stagnant in the fashion department. I’m not sure whether it’s down to the anti-climax after the Christmas break, the intention to live a little bit more austerely (for January at least) or whether the nondescript weather has to play a part. I know many of you love January (as stated in this post that Lauren shared last year) but for me it just feels a bit bleurgh and consequently my wardrobe follows suit.

When I shared this with the team, many of the other girls agreed which then led onto a discussion about our favourite fashion purchases of 2016 and those buys that weren’t say… quite as well thought out. And then we knew we just had to share them with you..from green jeans to velvet ski pants and some questionable see-through skirts, we’re revealing all this morning…


Three fashion disasters from my youth and childhood spring to mind. Firstly, my mustard/orange/brown splodged velvet ski pants that I so proudly wore when I was eight years old. (I now have a phobia of velvet; these probably explain why). Secondly, when I was around sixteen, I was a big fan of any Morgan top, so long as it had the brand name emblazoned across the front. And another favourite from my late teens was a combination of a pretty baby doll dress teamed with Reebok trainers. Oh the shame! Rich actually bought me some copper Reebok Classics for Christmas which look pretty epic but they don’t actually go with anything in my wardrobe so sadly they are going to be taken back today and probably swapped for some plain white ones.


Green jeans circa 1995. What were they all about?! I remember the day before ‘non-uniform day at school’ being utterly desperate for my mum to come home from town with a pair. My top of choice was a purple checked flannel shirt. What a combo.

More recently my summer capsule was an absolute flop. I ordered two dresses that clung to every lump and bump and meant to return them but inadvertently scooped them up in a pile of washing and so couldn’t take them back. Such a waste of money!


As much as I absolutely adore a denim skirt I just don’t think they suit me. I’d been eyeing up a black frayed version from New Look for a looong time very similar to this Topshop skirt, toying with the idea of whether or not I should take the plunge and buy one. In the end I ordered it on-line but sadly it has only been worn once as I just felt too self conscious in it. Maybe I should have opted for the tall version…..

Some of my most regrettable purchases were actually part of my wedding attire. I was suckered in to buying a pair of traditional wedding shoes from a bridal boutique I visited rather than trusting my gut, blowing my budget and ordering a pair of Louboutins. Then there was the hair piece which I had specifically made. It was very lovely, but far too big for my head. In the end I just wore an antique broach.


Green Dr Martins, waistcoats with swirly patterns, baker boy caps, chokers, those springy sparkly gem things you twirled into your hair, peasant style camisoles with the drawstring bust…oh the tragic list of fashion mistakes goes on and on and on. That said, like all of the team’s recollections above, these sartorial errors were very much of their time and I have no doubts that we’ll look back in ten years and ask ourselves what the hell we were thinking at those outfits we’re wearing as I type.

Perhaps one of my most shameful teenage fashion disasters is actually captured on video at the birthday party of my younger sister where I wore a white stretchy (think leotard material) long skirt with a slit up the front. I can remember thinking at the time that I looked like the cat’s pyjamas but when faced with the actual reality when I viewed the footage of said party last year every fibre of my being cringed with embarrassment. I can’t believe my mum let me wear something so distasteful…don’t even get me started on how see-through it was either.

I’d like to say I’ve learned from my mistakes but that didn’t stop me purchasing a fringed black mini/maxi skirt from Zara earlier last year. The model looked particularly awesome in it and so in my manic shopping haze there was a rather ridiculous part of me than thought I’d look the same too. Ha ha ha. Note to self…you are not 5ft 8 with legs up to your armpits Lolly so you will never in a million years look the same as that gazelle like Zara model. Suffice to say it’s gone into my January eBay pile.

What are your biggest most embarrassing fashion mistakes? Anything you’d care to share with us? And was there anything you purchased in 2016 which is doomed to languish at the back of the wardrobe forever more? Why not share your secrets in the comments box below…we promise we won’t tell.

Author: Lolly
Lolly is a self-professed frustrated florist and styling maven with an endless passion for all things pretty.
Follow Lolly on instagram @graceandgable

15 thoughts on “Our Biggest Most Embarrassing Fashion Mistakes

  1. Too conservative now but going back to the late seventies, yes, all your readers aren’t, thirty-somethings, shock! Going to the Rum Runner nightclub in Birmingham in full cowboy fashion, grey blouse and skirt with black fringes, white leather cowboy boots with red stitching and to finish it off, a red neckerchief and a gold sheriff badge, so wish I’d had a photo! Mind you, in those days you had to be picked from the crowd by the bouncers to make sure you were “cool” enough to go in. Obviously we all looked as ridiculous!

  2. Love the image you’ve just put in my mind Eileen – I’m thinking Jessie from toy story all ready to go to a night club!
    When I started going clubbing the rage was Lycra shoestring strap maxi dresses. I had a white one (totally see through and with a big split up one leg) a red one (bought from a posh shop in a sale so actually one of the better choices) a black one with a mesh back which was covered in glitter splodges. Non of these allowed for a bra and in those days there weren’t fancy atrapless or backless bra options available – I was a DD by the age of 16 so you can only imagine!
    Oh and the shoes I teamed this with were those bubble wedge Velcro strap one like the spice girls wore. Wow I thought I was ace. Happy to say I moved on quite swiftly from the Lycra dresses. But then came the fashion of dressing up jeans to go out so various pairs where bought, yet again with glitter adornments and all sorts of crap on them to make them look ‘dressy’ shameful. Don’t get me started on the hair.

  3. Oh lord! I think sixth form was probably my worst phase, tiny tiny mini kilts and shirts bulging with boob, more was more obviously…

    Also Lisa I had a Morgan case for my Nokia brick first phone- cooler than cool!

    1. I loved my Morgan stuff! My favourite top was a baby pink one with ‘Morgan’ written across the front in dark pink glitter ?

  4. So many fashion disasters throughout the years……. Without a doubt the absolute worst has to be the yellow dungarees I wore when I was about 14 to a party. I thought I looked amazing!!! Ha, ha – this was 1981 and they came from this cool jean shop in town.
    Another strange phase that both me and my elder sister went through in our early to mid twenties was wearing clothes that were just far too old for us! This was early nineties and we both wore lots of suit type outfits with big shoulder pads from places such as Alexon. What were we thinking?

  5. Lauren, I had a pair of green jeans circa 1995 too! I loved them so much. Spotted mine with a white Levi’s tee, matching green/brown waistcoat, and a green cord pork pie hat. I was quite the stunner in the ensemble… topped off with a corkscrew perm. That was also the era of many a black leggings/baggy flannel or denim shirt combos. And did anyone else have Ellesse trainers?! I saved for ages and bought a pair on sale with my own money, I thought I was cooler than cool.

    1. OMG I had purple Ellesse trainers that I LOVED that I wore with everything – regardless of whether it worked or not…floaty maxi dresses and short short mini skirts – I really didn’t care!

  6. Lolly chokers are already back in. Popped into top shop last weekend on a whim and the place is hoaching with chokers, and even worse dresses with built in choker attachments. Am clearly far too old now for topshop. Booo x

    1. Oh my god…really Rachel?? I think I stopped shopping in there about a year ago…with the exception of dungaree dresses and the odd skirt. I know exactly what you mean though..everything is just so short, or revealing or just too flimsy. I sound exactly like my mum…

  7. I can remember feeling so cool having a checked dolly/pinafore dress when I was 12. I loved it so much! I really wanted to look like Lauren Laverne (still do!) in her Kenickie days. I don’t know if I can bring myself to call it a fashion faux pas as it was one of the first outfits that made me feel grown up, but it was definitely an outfit of its time!

  8. There was a period when I basically walked around like an extra from Clueless, all a-line mini skirts, over the knee socks, Mary Jane shoes and twin-sets / angora knits / cami’s over t-shirts. I mean, way harsh, Tai.

    My biggest fashion mistake came not so long ago. I decided to wear an amazing leather shift dress to my best friends hen party, now it was technically Summer but as those of you north of the border know, it’s never really ‘Summer’ in Scotland. Except for that one warm day we sometimes get in July / August…

    Anyway, I was wearing said amazing leather dress on what turned out to be the hottest day of the year. Come 9pm I really needed the loo but found that I was unable to lift my dress over my thighs. I had a proper Ross from Friends moment (in the one with the leather trousers). I don’t think the bride-to-be would ever have guessed she’d spend her hen night locked in a cubicle with me trying to wrestle my clothing from my body but she did. That’s what best friends are for right?!

  9. My clothes shop of choice as I was approaching my teenage years was Tammy Girl. I wanted absolutely everything in this shop (my mum hated it and I was rarely ever allowed anything in there). I remember picking up a lovely co-ord set for a party, those tank tops with matching trousers which had an in-built skirt over the top – think s club 7. What was with those?! I was also in love with my baby blue shott jacket (yes I was a chav!) Up until the age of 18 my wardrobe choices were hideous!!! I also had a pair of those really baggy combat trousers with all the tassels hanging off! Oh the shame xx

  10. So the first one is actually quite odd because I had a t-shirt which was black & grunge in style which said ‘Malcom x’ on it, I was about 11 years old so to be honest I had no idea who Malcolm X was!! I think I just liked the big x or something! Can’t believe my mum let me where it?!
    Second…was a black bomber jacket when I was 14 that had ‘fantasia’ on which was a rave venue (which I had never actually been to!) but black bomber jackets were very in.
    Lisa – my good friend Karen & I loved Morgan so much we got a Saturday job there! We thought we were so cool :)))

  11. Lyndsey I will join you with your Clueless phase. We had no school uniform and for a time my best friend and I would go regularly to London to Soho to buy our school clothes (travelling from Sheffield) and kit ourselves out in matching PVC mini skirts and jackets in pink, red and blue, leg warmers, and boutique goodies. We’d squeeze into age 2-3 Postman Pat T shirts from mothercare (a cheap way to do crop top) I also had the green DMs Lolly, but mainly did the baby doll dresses with surplus army boots that were at least 4 sizes too big. A little clueless, a lot Shampoo and a fair amount of Bubble from Ab Fab…Every day. To school. Always red lipstick, always bleached blonde hair and never ever in jeans. I absolutely loved it and have no regrets. In contrast I now live in navy, black and denim and circulate about 6 outfits. I think I used up all my fun in the 90s.

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