Embarrassing Things I’ve Worn Growing Up!

I found myself chuckling the other day reminiscing on some of the things my Mum would allow me to wear when I was little. Don’t get me wrong, I wanted to wear all of these items, I remember absolutely loving them and thinking I looked good! I just wish my Mum/ somebody… anybody told me how hideous they were. I  thought this could be a funny – mostly embarrassing post and you might have to hold your head in shame too!

Embarrassing-Things-I-Wore-Growing-Up-2000s (13)


I remember wearing a poncho to school like there was no tomorrow. I actually called it a shawl back then! I used to wear this religiously to school on top of my polo shirt! Ponchos / capes of course came back in recently and were everywhere last Winter but this one above – and to school?! Just no. So, embarrasing. I have a school photo in it too and it’s just so cringe to look back at!

Embarrassing-Things-I-Wore-Growing-Up-2000s (1)

Fluffy Boots

I literally don’t even know what to say. I remember loving these boots and making my Mum rush and buy me another pair when the pair I had ruined. I just really don’t get what was going through my head?! They’re literally hideous and considering I really love my fashion now, why did I think these were OK?! Again, I used to wear these to school with a skirt and tights hahaha Oh my gosh.

Embarrassing-Things-I-Wore-Growing-Up-2000s (1)

Miss Sexy Trousers

I’m pretty sure most people went through the Miss Sexy phase didn’t they? As I’m tall, these used to be too short on me so I didn’t enjoy this phase for long but why oh why?! It’s funny really how us year 7/8s thought we were sexy in our little Miss Sexy trousers from bloody Blue Star! Cringe.


Embarrassing-Things-I-Wore-Growing-Up-2000s (15)

Trouser Skirt Combo

Another thing I remember absoutely loving and I actually remember when they were no longer available, feeling really upset!! I used to love being able to wear a skirt and trousers at the same time! Not quite sure why a skirt and tights wasn’t good enough but hey ho. I just don’t get it at all though now! Just to clarify, I would not have worn boots with them, my fashion sense clearly was bad for me to wear them but that’s even pushing it for year 2 Kaiesha.


Embarrassing-Things-I-Wore-Growing-Up-2000s (18)

Velour Tracksuit

All I have to say first of all is HA and Why?! I owned a few colours of these and I had a baby pink one that I used to wear all the time. Pretty sure me and one of my good friend Jade used to actually have matching as well as our matching England tracksuits during the World cup! I actually own a sorta velour tracksuit pyjama set at the moment because it’s pyjamas but I wouldn’t dream of stepping outside in a velour tracksuit anymore. I remember when everybody wore them though!


Embarrassing-Things-I-Wore-Growing-Up-2000s (17)

Skater Jeans

I used to love Busted. If you know me now I think that would be absolutely hilarious to read but I did. I also really liked Avril  Lavigne when she first came about and because of this … skater jeans with chains down the side were my thing. As disgusting as they were, I really liked the style of a fitted top and baggy jeans and that’s a style I still love now but skater jeans for a sk8r girl? No thanks. Not anymore!


Embarrassing-Things-I-Wore-Growing-Up-2000s (4)


What do you wear with skater jeans? Wristbands with a built in watch of course! I have a photo of me and two of my siblings looking very chubby, led on our living room carpet and I’m wearing a bandana and one of these in bright pink! It’s so funny to look back (if you want a laugh, scroll back on my Instagram, it’s on there!)


Embarrassing-Things-I-Wore-Growing-Up-2000s (7)


The trusty bandana I just mentioned! Bandanas still kinda come and go but I’ve definitely left them in the past. I used to think I looked so sick.


Embarrassing-Things-I-Wore-Growing-Up-2000s (10)

Cowboy Boots

This is one that embarrasses me the most. I really really don’t get why I liked these and again why my Mum let me leave the house in them? I actually had a white pair as well, like the photo I chose isn’t just a coincidence… I had a pair basically the same. Ew ew ew.


Embarrassing-Things-I-Wore-Growing-Up-2000s (3)

Chinese Slippers

Haha. Literally no words.


Embarrassing-Things-I-Wore-Growing-Up-2000s (2)

This Sexy Belt

This just makes me cringe. Imagine me in this with my cowboy boots? Beeeeeeautiful!


Embarrassing-Things-I-Wore-Growing-Up-2000s (5)

White Eyeshadow

I used to experiment with makeup a lot when I was little and one of my favourite looks was white eyeshadow with the occasional blue mascara. I’m not a white eyeshadow fan at all, even now. The most influential person in the world could pull off an amazing white eyeshadow look and I’d still absolutely hate it so don’t ask why I loved it back then!


Embarrassing-Things-I-Wore-Growing-Up-2000s (11)

Very Thick Headbands

I have a big forehead and without making this a depressing post, it’s a feature of mine I despise so I’ve always hid it and still do now with a fringe. When I was little, I used to do this by wearing a thick headband and wearing it on my forehead as opposed to back in your hair to actually hold your hair back.  It’s sad really that an insecurity caused me weird tan lines and it also made my hair line really thin and weak but it’s funny to look back on I guess!


Embarrassing-Things-I-Wore-Growing-Up-2000s (16)

Neon Beads

Why oh why did I wear this and tie a little knot in it? I had so many colours and I remember they used to get tangled and I’d spend so long untangling them!


Embarrassing-Things-I-Wore-Growing-Up-2000s (1)

Tops With Prints

I’m getting a little older now, going to my first Nappy nights! One time, I wore a black top with pink neon hand prints on my boobs (I was 13-14), neon pink bracers and neon pink leg warmers! I gained an obssession with printing on tops and writing things like Kai Kai with stars and whatnot. Gosh.


Embarrassing-Things-I-Wore-Growing-Up-2000s (12)

Neon / Colourful Laces

While on the topic of neon, I used to own so many different colour laces and there was a particular way of lacing up shoes with particular bows and sometimes even more than one lace. There was even a phase of wearing shoe laces in hair as a headband (this time it was actually on my head, I didn’t attempt to conceal my forehead with numerous different laces).  


Embarrassing-Things-I-Wore-Growing-Up-2000s (14)

Printed Leggings

When leggings came back in and everywhere started selling crazy printed leggings. I was weird with this one, I used to like them back then but I just couldn’t pull them off because I’m so tall so I’d buy them and then never ever wear them. The ones I remember the most were the different colour paint splat ones H&M used to sell. This was when I was in year 8-9 so, 2008-2009. So funny. I despise leggings now. Don’t know what it is, I’m just a jeans/ trouser kinda girl.


Embarrassing-Things-I-Wore-Growing-Up-2000s (8)

The Slick Fringe

Another one that if you know me, you will laugh. I picked up this fringe style when I was in about year 5 and I wore it I swear until I was in year 9. That’s a good 4 years of intense gelling my hair. I was never a spotty teenager though, so maybe it has a hidden beauty trick within their somewhere?! I also used to do the little curls with my sideburns haha I don’t even find this one that embarrassing, it makes me laugh at the dedication I had whereas now I’m so lazy with my hair most days!


Embarrassing-Things-I-Wore-Growing-Up-2000s (6)

Wearing Hoodies Incorrectly

I’m proud to say I actually didn’t do this one but it’s definitely one I have to mention. You know when American Apparel initially made the colourful jumpers with white strings famous and everybody owned one and used to think they were a superhero by tying up the strings and wearing it undone? Yeah I didn’t get it.

That’s all for this post. I’m certain there are many more embarrassing things I used to wear so when I next get the photo album out, it might mean a part two!

Are you guilty of any of these?


BloglovinTwitter | Instagram | Pinterest

all images taken from Google Images


  1. Anonymous
    May 29, 2016 / 2:12 PM

    Omg Kaieshs, I so relate. I was also thinking of leg warmers, especially sparkly ones. (They weren’t awesome if they weren’t sparkly). Thanks for the smiles, and have a wonderful rest of your weekend.

  2. May 29, 2016 / 6:13 PM

    Haha I always wore a poncho, a proper knitted on too! Haha! & that belt

  3. kaiesha stewart
    June 1, 2016 / 10:46 AM

    Haha oh gosh I too wore leg warmers! Glad you liked the post, hope you had a great weekend too!

  4. kaiesha stewart
    June 1, 2016 / 10:47 AM

    Haha what were we thinking!

  5. kaiesha stewart
    June 1, 2016 / 10:47 AM

    We all were embarrassing!

Leave a Reply

Your email address will not be published.