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Everybody’s look changes over time, from massive overhauls to subtle shifts the way we look is constantly evolving. Today we are going to share the way our tastes and styles have changed and what influences have prompted this.


I used to wear black a lot, I think I wore black every single day during my early 20’s along with huge oversized clothes and patterns that highlighted my size. For work I would wear a pair of black trousers with a red or purple shirt. I rarely wore dresses and possibly owned one pair of heels and had three pairs of shoes in total. Even my handbag (just the one!) was black. It is incredible to me now looking back to think how rarely a print or a different colour worked its way into my wardrobe. I was waiting until I was pretty (which in my head meant skinny) to buy nice things, I thought I would seem ridiculous if I bought a nice dress or pretty shoes, that people would think less of me because I was trying to hide the fact I was over weight.

The big thing that changed for me was that I forgave myself for being imperfect. I’m not saying I stopped caring about being healthy and fitter, because I do still care about that, but it did mean I stopped punishing myself for being fat by hiding myself under layers and wearing poorly fitting clothes. This commitment to looking as good as I can given who I am right now lead to a style that is probably best described as feminine and colourful. I wear colours and pattern every day and while black still features in my wardrobe I make sure I break it up with accessories and prints as much as possible.

The best part about being ok with yourself is that it is actually much easier not to buy the ill-fitting and ill-suited things because you are not competing with that horrible voice in your head that tells you it doesn’t matter what you wear you’ve already failed. The affirming fashion thought cycle goes something like this: feel slightly better about yourself, buy nicer clothes, get compliments about how nice you look, feel even better, take more care with your appearance, feel slightly better about yourself…. lather, rinse, repeat.


My answer to this is very much the same as Becs! I wanted to hide from the world and wear what I thought nobody would notice me in. Looking back now I can see how wrong I was.

I feel grew up a dirty child and when I say this I mean always roughing it up with the boys. I had only male cousins to play with and I’ve always had trouble keeping female friends. I had the occasional dress and wore mostly short/shirt combos. During my teenage years I NEVER had a handbag, flats, skirts/dresses. I always wore sports branded t-shirts like ADIDAS, Nike and stuck to cargo pants and does anyone remember those zip-off jeans from JayJays, with the fluoro trimming? I was always extremely self conscious of going out with my friends who were well into fashion before I was.

I was constantly fumbling with my keys, mobile and wallet in my hand as I didn’t have a handbag to carry anything in because I thought it was a “girl” thing to have. Looking back now I don’t know how I ever survived without a handbag! Now days I carry a LOT of different things, I guess growing up comes into play as well. I have more things I need to keep with me as I travel.

I continued to wear the same shirts and boys shorts until after I had finished high school. While most girls in my senior class wore dresses I was one of the few who stuck to boy shorts and a polo top. I just felt like I didn’t belong in a dress during high school years.

It wasn’t until I started seeking work I became far more aware of dressing femininely, and I found classic black skirts in Target and collared button shirts from places like Susans, Katies, Kmart and Target etc. I’m sure my Dad & brother were most relieved when I got out of that tshirt phase, I used to raid their cupboards ALL the time.

Before & After

After moving to Sydney for a boy ( 😉 ) I started to wear a lot more girly clothing. Lots of skirts, tops and cardigans. It wasn’t until I met Amy I was confident enough to buy a dress on my own and wear it out in public. Now I live in dresses and maxi skirts, which I’m slowly branching out into different styles and patterns.

I seem to have given you a GIANT wall of text, but I wanted you to get to know *me* 🙂

Caitlyn xo

Do you have any fashion evolution stories? Share them with us in the comments below.

What things influence how you dress now, has it always been the same?