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My Style Evolution: From my 20s to my 30s

April 12, 2020 6 Comments

Turning 30 this year has given me a decade’s worth of lessons and memories to reflect on. My 20s felt like a well of wisdom, slowly filling up and culminating in the knowledge that there is still so much I don’t know, and nobody really has it figured out.

I grew – sometimes painfully – in every aspect of my life. But one great joy that I can happily reminisce about is how I developed my personal style. I went from thrift shop chic (read: hipster), to full-fledged flaunting of the latest trends, to figuring out what works best on my body, and what I feel most comfortable in.

Shall we take a little stroll down memory lane?

Early 20s

I have to give so much credit to my retail store job at 18 – I worked at Mendocino, a gorgeous Toronto/GTA-based boutique. Mendocino broadened my horizons, and I learned about really cool contemporary brands from around the world.

Because I was making probably $12 an hour part-time, I supplemented my love for premium denim and expensive trends with thrift store finds. This is something I still do now, perhaps with a little less of a penchant for novelty items and more for classic, timeless pieces.

Mid 20s

I was entirely inspired by bloggers, and eventually started my own (thanks for reading :)). I had even more fun with fashion, picking out weird things that really didn’t go together, and truly embracing the ethos that I was a woman who never dressed to catch a man’s eye, but for other women, and most importantly, for myself. I coveted cool outfits, and started investing in designer pieces. Most of my current wardrobe foundation was collected during this time.

Late 20s

By my late 20s I had stopped shopping for trends, and instead bought pieces I knew I would get a lot of wear out of, which also suited my body.

I used to have lots of pieces in my closet that would only work when paired with specific items. For example, I owned a sparkly top that was too tight, so I could only wear it with this one pair of high-waisted pants. Or a beloved tulle skirt that was so voluminous, I only ever wore it with a particular black tank top.

I’ve since streamlined my closet so that I have a much easier time combining all the pieces I own. It takes the stress out of getting dressed in the morning, and I always feel put together. I still have plenty of jollifiers (flamboyant novelty pieces) to keep my style feeling true to myself 🙂

One thing that’s been consistent through the decade is the confidence I felt, and still feel, when getting dressed. I’ve always felt completely at home in my outfits, and I think that’s the key to finding personal style.

Thank you so much for reading, and for taking a look back over the years with me 🙂 If you have a favourite outfit, I’d love to know in the comments! Xox


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  • Laura April 13, 2020 at 9:39 am

    I’ve always admired your style – I absolutely love the way you style your blazers and your coat collection is perfection!

    • jocelyncaithness April 17, 2020 at 8:11 am

      Love you! Many of my favourite outfits have been with you, gallivanting around Europe 😉 xox

  • Linda April 14, 2020 at 3:47 am

    You are perfection Jocelyn!

    • jocelyncaithness April 17, 2020 at 8:10 am

      No, you are!! Missing you <3

  • Rizwana April 16, 2020 at 11:28 pm

    Ekkkk you are too cute and lovely! The sweetest and most beautiful Fashion Diva 🙂

    • jocelyncaithness April 17, 2020 at 8:09 am

      Thank you SO much for reading <3 <3!!

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    About Me

    About Me

    Hi, Friend!

    I'm Jocelyn: a daydreamer and fashion lover disguised as a finance professional. My head may be in the clouds, but my stilettos are firmly planted on the ground ;)

    Jocelyn Caithness

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