In Discussions, Style

Was there a point in your life when your style changed dramatically?

It was probably near to the end of high school, around the same time this guy said something about my eye-ball neon orange searing jacket.

Before then, I had dressed sort of unobtrusively. I dressed to NOT get noticed, to blend in, not get made fun of, and to be comfortable. I never wore anything that announced I was a girl, and in fact, dressed as if I wasn’t one.

Think: Grey v-neck ribbed t-shirt, $5 from some bargain bin in a sad little strip mall near my house that I was allowed to walk to alone, and some cheap Zellers (remember them? defunct franchise?) black jeans, with a round butterfly choker and some black shoes.

Ugh. Terrible.

The image is seared into my brain.

I dressed like all the other nerds, because I was loftily and very insecurely trying to announce that I had a brain, and therefore did not need to look like a girl or attract anyone to try and be pretty because it was meant for those who didn’t have brains….. never mind the fact that no one was actually attracted to me!

Also, no pink or purple, or flowers.

I was a sexless jellyfish.


After he made that comment, my braces came off (FINALLY), and I got contacts for the first time, being able to afford them from my part-time job.

Glasses off, braces off, new look onto my femininity and suddenly I was reborn, style-wise.

I wore a skirt for the first time since I was 9, and I became who I am today.

Now I’ve embraced skirts wholeheartedly.


The entire series can be found here: Women in Clothes Style & Fashion Survey

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Sherry of Save. Spend. Splurge.

Am my own Sugar Daddy. Am a millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using I have worked 50% of my career (taking 1-2 year breaks), and quadrupled my income within 2 years of graduating, going from $65K to $260K with an average lifetime savings rate of 50%. I have 11 side incomes that are on track in 2020 to make me $50K - $75K. I could retire today if I wanted, but love my work-life balance as a freelancing consultant in STEM (Science, Technology, Engineering, Math). I am all about balance - between time and money, and also enjoying my money. I also post daily on Instagram @saverspender.

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Posted on January 15, 2017

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  1. Corianne

    It wasn’t sudden, but during a period abroad, with some weight loss, I ended up buying more and more dresses… now I almost only wear dresses, or some skirts. 1-2 days a week, a pair of pants… Quite a transformation, from jeans and t-shirts to nice dresses in nice colours which suit me…

    1. Sherry of Save. Spend. Splurge.

      How do you deal with winter? Tights?

      1. Corianne

        yes, more than enough usually – though winters in Belgium/Netherlands will probably not be as cold as in Canada!? 😉

        1. Sherry of Save. Spend. Splurge.

          Canada is freezing. I breathe the Arctic air ..

  2. Izabela

    I changed my style when my baby was born. I spend 9 month breastfeeding and after that I came back to the WORLD. I was so over my home clothes that I needed to shake off everything what was connected with sitting at home. I started to look smart, professional… and I started to wear clothes for me and only me. Before that I was taught I should not be overdressed (now i think – what does it mean)… but know I understand that overdressed looks bad only when you are not sure about the clothes, when you are uncomfortable with it. But who can stop me from wearing a cocktail dress and make-up in the morning when i want to have a nice cup of coffee in my favorite Cafe? It’s like “Breakfast at Tiffany’s” just for me.

    1. Sherry of Save. Spend. Splurge.

      I DO THIS!!!!!! I SO DO THIS. I am so happy to hear that. I wear bodycon but comfortable dresses out with short heels with Baby Bun, and people give me the strangest (but appreciative I hope) looks, like I should be in stained yoga sweats instead.

  3. Tania

    Yes, very recently, in the past 5 years. I used to be girly rocker and love lots of extra details. Now I can’t stand it (on me, I can still appreciate it on other people). I’m now more of a classis minimalist mixed with a tomboy. Occasionally a boho but nothing like before. I think it’s my age (48 now) and also finally knowing my own style, not caring what others think, realizing simpler looks better on my curves, craving comfort above all else and having a creative outlet other than what I wear. I think we will all go through various stages in life. However, I think my current style will serve me well beyond my current middle aged stage.

    1. Sherry of Save. Spend. Splurge.

      I still like rock details but not overt ones….


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