Dressing Like the Cool Kids

I’ve been at a loss lately about what to wear. Nothing feels right. I hurt my back a couple months again and fell into the yoga pants habit for comfort. Then the excuses were: it’s only shopping, walking the dogs, driving the kid to school, visiting friends for coffee etc. It’s really snowballed lately. 

A couple weeks ago I was invited to an influencer event with people who engage the public via social media. Since the location was Forest Hill in Toronto I was pretty sure yoga pants wouldn’t be ok to wear. So I went to the closet and made some decisions that I thought were pretty ‘hip’. 

Upon arriving at the venue I realized I was terribly mistaken. In my excitement to layer I’d put one thing on that was too short, another that was too long and of course, the winter boots were a big mistake. I felt so frumpy. 

Coupled with this lack of basic fashion knowledge is the fact that my body shape has changed over the past few years. I’m just not sure how to dress myself to feel comfortable and look ‘not frumpy.’ 


Enter my best friend and partner in crime Micheline Kerswell. Miche owns an amazing consignment shop in the village of Port Hope, Ontario called My Sister’s Closet. She specializes in higher end brand name clothing and shoes for women from size 0 to ‘voluptuous’. She also has a section for men’s clothing too. 

Miche decided it was time to step in and save me from my own fashion sense. 

Her challenge was to find something I could wear to these influencer events that I was comfortable in and did not include yoga pants. 

Based on my figure, (I’m larger up top,) and age of 48, (but want to look 38,) and my most definitely voluptuous figure, she came up with this formula to help me plan my outfits:

skinny jeans/pants

shirts that extend below the waistline

layer a nice long jacket on top of it all with sleeves rolled

funky jewelry

a pop of colour on my feet

This is what it looks like:


To be honest the pants were a little out of my comfort zone since they are so revealing. However, many compliments later I feel maybe they aren’t so bad. (Plus they are teenager approved!)

Overall Fashion

I’m very happy with this outfit and the pants are as comfortable as my yoga pants – bonus! I love the red shoes, and I like the option to have the jacket on or off depending on the temperature. By wearing a top that goes below my waistline, my body looks longer in the torso and the open jacket makes me look more slender too. 

I’m ready for my next influencer gathering! fashion

Thanks Miche! 


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