Kim Flanagan | Calgary’s Best Dressed 2026

As a fashion stylist for the past 20 years and a volunteer with Dress for Success, Kim Flanagan has learned that honouring your personal taste trumps adhering to fashion “rules.”

Dress: Ciebon (from Who Cares); Vest: KaaDiki (local designer); Bracelets: Zara; Boots: 3.1 Phillip Lim. Photo by Jared Sych; Styling assistance by Park Production House; Hair and makeup assistance by Michelle Simoneau-Clayton. Shot on location at Bankers Hall and Bankers Court.

How did you figure out your personal style?

“Probably with my parents, because we were taught that getting dressed is manners. It takes it off yourself, and instead becomes care for where you’re going and care for who you’re gonna go see.”

 

How does your style affect how you show up at work versus outside of work?

“I show up the same at the dog park as I do at work. If a vibe is the vibe, then that’s what I go with.”

 

What advice would you give someone cultivating their own style?

“Ditch any fashion rules that you have, they’re stupid and they hold you back. Say yes to yourself instead of no. I would never pick the clothes that I pick for myself if I followed my body type. Be attracted to what you’re attracted to, and then actually just try it on.”

 

Dress: Brunello Cucinelli; Oversized blazer: Opt (from Wilder’s Consignment); Broach: heirloom (from her mother); Shoes: Stuart Weitzman; Purse: Manish Arora. Photo by Jared Sych; Styling assistance by Park Production House; Hair and makeup assistance by Michelle Simoneau-Clayton. Shot on location at Bankers Hall and Bankers Court.

 

What is your favourite piece you own?

“My Lenny Kravitz coat! It’s a Trina Turk coat that looks like white feathers. Every time I wear it, I pray that I’m gonna run into Lenny Kravitz. It’s a rockstar coat, it just feels good.”

 

What is your favourite designer or place to shop in Calgary?

“I do well at Vespucci, I like looking for treasures and I generally find one there. In terms of designers, Paul Hardy and KaaDiki.”

 

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This article appears in the September 2026 issue of Avenue Calgary.

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