Beyond the Small Talk: Changing our conversations about clothes

Complimenting someone’s outfit is a great way to initiate small talk and make a quick connection. It can also bring a smile to their face.

I recall a memorable encounter with one of the bosses at my work, who I admired for many reasons: she is smart, confident and always impeccably dressed.

One morning as I made a mad dash for my desk, I spotted her out of the corner of my eye. Suddenly, she was looking in my direction. “Great top.” she said. Like a starstruck fan girl, I managed to squeak out a ‘thank you’ and told her where I got the top. “Good to know,” she smiled.

My spirits quickly took a upturn from my disastrous start to the day. I had stayed up the night before to prepare for a nerve-wrecking presentation. After hitting the snooze button a few too many times in the AM, I was left with less than five minutes to put together a presentable outfit, only to have spilled water all over myself before heading out the door. Her comment gave me an instant boost of confidence.

But wait, why did I tell her where I got my shirt from? First of all, she certainly did not need my fashion advice. Secondly,  she didn’t even ask. Why was that the first thing that came out of my mouth?

While I would like to berate myself for making such a comment, I have to accept that this is a common response. If we think back to our water cooler chats, a small talk about clothes usually leads to a verbalized catalogue of brand names, retail stores and how to score the “best” deals.

We share this information as a way as a service to others. After all, who doesn’t want to be “in the know” or be perceived as an expert? However, these conversations are largely driven by the basics of consumption, generated by fashion marketing efforts, to create a need to acquire more clothing at the lowest price possible. 

Photo by iPrice Group from Pexels

What if we steered about from the frivolity of fashion and focus on the experience? What if we went beyond the small talk and share the stories behind what we wear?

The nature of small talk is non-controversial and brief, so it can be difficult to get past the superficiality and frivolity of the topic. When we share a piece of ourselves, you might be surprised to find that vulnerability can open up doors to more meaningful connections.

For many, style is more than labels and price tags; each piece tells a unique story. Style is embraced as an outlet for expression and reflects diversity and individuality. It is the story beneath the clothes that makes it unique. Our experience and emotions attached to the piece ultimately determines its value.

One of my favorite items in my closet is a pair of black leather slouchy boots with double buckles, acquired during an unforgettable trip to Spain with a group of friends I’ve known since university. Everytime I put them on, I am reminded of the unexpected adventures and the warmth of locals we met along the way.

Whenever someone comments on these boots, I feel compelled to share the highlights of the trip: how I wandered into the tiny alleys of Madrid and discovered a whimsical little boutique, how difficult it is the shop when you don’t speak the local language and how I met a lovely sales associate who searched the entire back room to find me the only pair of size 6 shoes left in the store. The boots carry with them a beautiful story about the universal language of kindness.


When we develop a connection with something, we also come to appreciate its history. As we learn to enjoy our experience with our garments, it challenges us to rethink our decisions as a simple financial transaction and retail thrill, and to consider its true value. We begin to appreciate the garment makers and resources that have shaped the garment, so we can weave them into the story of our clothes. 

Next time you strike up a conversation about someone’s outfit, be curious and listen. You might learn something new about the garment and the person.

And if you are the lucky recipient of a compliment, share your unique story.

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