In Discussions, In my closet, Minimalism, Style, Style, Women

Style Evolution: How I have changed over the years [NOW]

You can read Part One [THEN] of my elementary, high school & college years.


I started realizing I had to be more career-minded and professional, so AGAIN, I went overboard and went straight into suits, pants, wrap dresses and so on.

That has never really gone away, but I have ditched the suits and have opted to only wear blazers with jeans to keep that masculine + feminine aesthetic alive.

I shopped a lot at Jacob and Smart Set for matching pantsuits, but oddly enough, never wore them together or at all. I just liked seeing them hang in my wardrobe to tell me: You’re now a professional.

I still have ONE full pant and skirt suit from when I bought it at Jacob a long, LONG time ago in the last year of my college before I started my job, and it has stayed with me ever since. It’s a tweed dark charcoal grey suit, and it has been my go-to interview suit for every time I need to trot it out. Fits like a dream.

I started veering into pencil skirts, buttoned-up tops and all of these kind of “business”-style wear, which has ended up being a running theme in my clothes these days.


You can see ALL of my outfits and filter by Work, Weekend, etc (just give it 30 seconds or so when you filter, that way it has time to load).

I look back at my style evolution over the years from when I was a kid and a few things still remain:


I very much enjoy bold colour and prints from when I was a child but now it is used in small doses.

It appears more in my jewellery than in my clothing, but I do have wonderful pieces where the skirt or the top is wild and colourful but still sophisticated without being too juvenile.

I find that my bags and purses stick to being more neutral than colourful these days, because I want them to go with everything, and sometimes a very colourful and wild bag is not as stylish against something that requires a plain cognac bag for instance.


I love me some leather, studs and grommets. I still can’t get away from liking all of that, but now it is in much smaller, more refined doses.

Leather leggings instead, or moto biker boots with few buckles, or even jewellery that is really strong and bold, but paired with more neutral or feminine outfits.

Or really great pieces of armour:


I still really like the structure of masculine clothing, but juxtaposed against feminine elements, like a soft silk white button-up shirt from Equipment underneath a strong wool blazer with some skinny jeans, and a really feminine, girly crystal necklace.

I like pairing very pretty things with very minimalist menswear.

Now, my idea of “pretty” doesn’t mean pink, purple, ruffles or frills, it means colour or print or a little pleat or draped item here and there, or a great printed scarf:

But when I take a look at what has changed, I am surprised to find that:


If it’s my top, or my skirt, or my jewellery, I only have ONE (if any) bright and/or colourful piece in my outfit. I am less inclined to mix prints and patterns altogether unless I think it would look cohesive.

I only want ONE really bright and colourful point to build an outfit around.


I have accepted that my shoulders are broad and a size bigger than the rest of me, and I should avoid puffed sleeves, spaghetti straps and halter tops at a minimum (which I do).

That is not to say that I never break the rules, but I am more aware that I am not comfortable and therefore feel less secure and happy in what I wear, if I am not wearing something that is confirmed in my head to ‘look good’.


This is why I can’t seem to get rid of half my wardrobe (or more) and just wear a few dresses or pants.

I have different personas, and some days, I feel beach-y, others, I feel girly…

Some days, I only want to wear girly, A-line feminine skirts with flowers.

Other days, I only want jeans and a t-shirt.

Other days, I want to wear a pinstriped bustier top and a light blazer and some riding boots or heeled boots.

…and if I am going to the playground, I still prefer jeans and a sweater or top, or a very simple jersey sheath dress for maximum movement & dirt control.

Whatever I wear, I feel better if I dress as who I am TODAY or who I want to be in my head for what I am doing today (I wouldn’t wear heels out to the playground).


I am choosing and gravitating towards simple outfits with less buckles, belts, and accessories.

I’ve been going more and more without wearing jewellery (even though I still love wearing and collecting it)..

Who knows what I’ll want in the future, but for now, I only want to feel ‘free’ and not so fussy.

Honestly, I think my partner’s side of the family has been influencing me more than I think. I always covet what the women on that side wear, no matter their age.


Psst! If you want to read about someone else’s style evolution, Adina’s has pictures & is comprehensive since 2009!

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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 May 29, 2018

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